Tinatin Bukia

Diazo compounds are organic complexes containing two nitrogen atoms bonded together. Remarkably, diazo compounds are among the most important building materials in the organic synthesis field. The research was mainly oriented to synthesize diazo and spiro center consisting new photochromic compound. Notably, perspectives of spiropyrans to design new photocontrolled molecular equipment and biological materials, logic valves, and sensors are not exhausted. Therefore, today, active investigation to design and study compounds with new properties are underway [1]. For this purpose, azo group containing compound spirochome was synthesized which is also illustrated on the scheme below: Initially starting compound - 2,3,3-trimethyl-5-nitro-3H-indole (1) was synthesized by nitration of 2,3,3-trimethyl-3H-indole. The quaternization of compound 1 with CH3I was performed in a shallow ampoule at 80-82 ̊C in the acetonitrile area and quaternized salt 2 was isolated. With further reduction of compound 3 with LiAlH4 in tetrahydrofuran

compound 4 was extracted, which reacts with 3,5-dinitro salicylic aldehyde (4) and gives a compound 5. For the organic synthesis, mentioned above, techniques like distillation, crystallization, extraction, column chromatography, etc. were used. After each step of the synthesis, the mixture was tested on the thin layer chromatography with the eluent of ethyl acetate/hexane 1:2 ratio. Furthermore, the final compound’s IR, UV and NMR measurements were performed and interpreted by corresponding spectra. Studies on synthesized compounds are ongoing.

The purpose of the following research is to prepare the Azo group containing derivatives with the help of the coupling reaction of 5-amino-2,3,3-trimethylindolenine and β-naphthol. Azo group containing derivatives generally represent compounds with ArN=N-Ar' structure (Ar - aromatic group). They stand for the most widely spread type of synthetic colorings used in various fields such as cosmetics, foods, pharmaceutical industry. In addition, azo compounds can be exploited as antiseptic and antimycotic uses. Received Azo compounds give the opportunity to synthesize spiro compounds, which are widely used in modern technologies, in light-emitting, nonvolatile memory, and photo sensing gadgets. Also, in solar cells and biological and chemical sensors. In this research, initially was synthesized starting compound - 2,3,3-trimethyl-3Hindolenine-5-amine (2) by the reduction of compound 1 using Sn/ conc. HCl at high temperature. The diazotization of compound 2 was conducted using 2 M HCl and HNO2 at low temperatures. To the solution of diazonium salt 3 was added beta-naphthol (4) in equimolar alkaline solution. The formed azo compound was quaternized using CH3I in a shallow ampoule at 80-82 ˚C in the acetonitrile and quaternized salt 6 was isolated. By the treatment of compound 6 with alkaline solutions and interaction with 5-nitro-3- bromsalicylic aldehyde was obtained compound 7. Studies on synthesized compounds are ongoing.

The main purpose of our research study is to create and manufacture the azo compound from coupling 5-Amino-2,3,3- Trimethyl indolenine and aniline, producing the diazenilaniline. Azo compounds have an immense role in synthetic dyes and organic pigments, considering their synthesis and a great number of substituents. Azo dyes consist of a chromophore group, a double-bonded azo linkage, that is responsible for producing certain colours. Azo colorants offer a huge range of chemical pigments and a wide spectrum of colours. The majority of azo dyes are water-solubility and used as colorings of natural textile, leather, paper, and plastic, but are slightly susceptible to colouring wool and cotton. Another application of azo dyes is in cosmetology and pharmacology for treating bacterial infections. The classification of azo colorants includes acid, basic, direct dyes, etc. Acid dyes are anionic ones, that are manufactured for colouring mostly textile, polyesters, silk, or used as inks and paints. Basic acids possess water-soluble cationic azo dyes, that are characterized by positive charges. They play a significant role colouring the polyacrylonitrile fibers. Direct dyes acquire electrolytes for dying, because of their water-soluble anionic nature, that are used for colouring the celluloid fabric. In this research, initially was synthesized starting compound - 2,3,3- trimethyl-3H-indolenine (2) by the interaction of phenylhydrazine (1) with methyl isopropyl ketone (2) in an acidic area. Nitration of 2,3,3-trimethyl-3H-indolenine (3) was performed by using a nitration agent (HNO 3 /H 2 SO 4 ) (1). The reduction of compound 3 was conducted using Zn with conc. HCl at high temperature. The diazotization of compound 5 was carried out with HNO 2 aqueous solution at low temperatures and coupling was conducted via aniline (7). The formed azo compound 8 was separated out in the form of a precipitate.

Understanding the chemistry behind spyropirans is of utmost importance due to their far-reaching capabilities. For this purpose, it was selected to carry out synthesis and research of spirochromes containing azo dyes. The spiropyran and azo dye are fused in an unexposed form, while after exposure with UV rays, the symbiosis of the two dyes (merocyanine and azo-) will occur. It is essential that at one end of the molecule we will have an electron-donating, and at the other end electron-deficient substituents. In fact, the visible spectrum area of the compound prior to exposure will have an azo dye spectrum following the nature of the substituent(s), and after exposure, there will be a joined, flat, conjugated chain spectrum of the two dyes. In this research, the objective was to synthesize and characterize new spiro compounds. Initially was synthesized starting compound - 5-nitro-2,3,3- trimethylindolenine (2) by nitration of 2,3,3-trimethylindolenine (1). The reduction of compound 2 was conducted using Sn with conc. HCl at high temperature. The diazotization of Obtained compound 3 was carried out using HCl and NaNO2 at low temperatures. To the clear solution of diazonium salt 4 was added beta-naphthol (5) in equimolar NaOH solution. The formed azo compound 6 was separated out in the form of a precipitate. The quaternization of compound 6 with CH3I was performed in a shallow ampoule at 80-82 ̊C in the acetonitrile area and quarternized salt 7 was isolated. The treatment of obtained compound 7 with alkaline solutions and reaction with different nitro salicylic aldehydes give a compound 10 and 11.

Azo-compounds are important in the dye and pharmaceutical industries. The usefulness of azo colorants is attributed to the ease with which they may be synthesized by diazotization and azo coupling; infinite possibilities are suggested by different diazo and coupling components [1]. This research relates to the preparation of 4-((2,3,3- Trimethyl-3h-Indol-5-yl)diazenyl)phenol from 2,3,3-trimethyl-3H-indolenine-5-amine. The coupling component used in our experiment was an electron-rich aromatic compound Phenol. Phenolic azo dyes have various benefits over other dyes, including a broader color range, high color fastness, and light absorption. In this research, initially was synthesized starting compound - 2,3,3-trimethyl-3Hindolenine-5-amine (2) by reduction of 2,3,3-trimethyl-3H-indol-5-nitro (1). The reduction was conducted using Sn with conc. HCl at high temperature. The diazotization of compound 2 was carried out in the area of HCl using aqueous NaNO2 at low temperatures. To the clear solution of diazonium salt 3 was added phenol in equimolar NaOH aqueous solution. The formed azo compound 4 was separated in the form of a precipitate. The quaternization of compound 4 with CH3I was performed in a shallow ampoule at 80-82 ˚C in the acetonitrile area and quaternized salt 5 was isolated.

The Passerini reaction is a multicomponent reaction that combines isocyanides, ketones or aldehydes, and carboxylic acid to make α-hydroxy carboxamides discovered by Mario Passerini in the 90s. This reaction has been studied for many years and has also been widely used in medicinal chemistry because of its fast and effective generation of similar molecules. With this research, we plan to synthesize an Adamantane derivative using the Passerini reaction to hopefully synthesize a compound with high biological activity. Adamantane and its derivatives have been used in pharmaceuticals for many years for their various medicinal properties, especially in one specifically for disorders tied to central nervous systems (CNS), improve the symptoms of Parkinson's, and is valuable for Alzheimer’s treatments. In the present study, the aim of our work was to synthesize adamantane moietycontaining derivatives via a Passerini reaction, carry out their phis-chemical study and bio-screening via an online prediction program and compare it with some adamantane moiety containing medication. The synthesis was conducted according to the scheme, by the interaction of adamantane-1-carboxylic acid (1) and ethylisocyanoacetate (2) with a different aldehyde (isobutyl- (3), 2-phenylacetaldehyde (5), and 2-hydroxy-5- nitrobenzaldehyde in the area of CH2Cl2 at room t°. The obtained product was purified using column chromatography (ethyl acetate/hexane 1/9 reaction mixture) and the structure of the synthesized compounds was proved by IR and NMR spectroscopy.

Multicomponent reactions (MCRs) are extremely popular owing to their facile execution, high atom efficiency and the high diversity of products. one of the classic MCRs includes the Passerini reaction. in this work, an efficient classic three-component Passerini reaction is conducted with ethylisocyanoacetate, 5-nitro salicylic aldehyde, and carboxylic acid and offers direct access to α-hydroxy carboxamides. The electrophilic activation of the carbonyl group is followed by a nucleophilic attack by the isocyanide. This creates a nitrilium intermediate, which is then attacked by the carboxylate. The passerine reaction plays a central role in combinatorial chemistry. In the present study, the synthesis was conducted according to the scheme, by the interaction of adamantane-1-carboxylic acid (1) and ethylisocyanoacetate (2) with a butyl aldehyde (3) in the area of CH2Cl2 in room t°. The reaction was monitored by TLC (Hexane/ethyl acetate 2/1 ration mixture). The obtained product was chromatically purified on the column by the standard method (SiO2, petroleum/ethyl acetate) and the structures of the synthesized compounds were proved by IR and 1HNMR spectroscopy.

More than half of the synthetic dyes are formed by the electrophilic aromatic substitution mechanism of an azo coupling part that contains an activated hydrogen atom that is bonded to a carbon. As Bis-Diazo dyes can be synthesized in laboratories, the desired colors can be easily obtained and determined by the azo bonds and their associated auxochromes and chromophores. These compounds also contain chemical groups that can form covalent bonds with the substrates of various textiles that contributes to their wide applications. Bis-Diazo dyes or simply Azo dyes not only play a huge role in the contemporary dye chemistry, but many scientists even think that their importance may highly increase in the future. These synthetic colorants are widely used in paper, printing, textile, leather, cosmetics, pharmaceutical, and even food industries. For this reason, the abovementioned compounds are the most abundant in the printing and dye market, for example, at least 60% of total dyes in the world are characterized as azo dyes. In this research, initially the starting compound - 2,3,3-trimethyl-5-nitro-3Hindolenine (2) was synthesized by nitration of 2,3,3-trimethyl-3H-indolenine (1). The reduction of compound 2 was conducted using Sn with conc. HCl at high temperature. The diazotization of compound 3 was carried out in 2 M HCl and aqueous NaNO2 strictly at 0-5 ° C temperatures. Next an acidic solution of equimolar 2,3,3-trimethyl-3Hindolenine (5) was added to the solution of diazonium salt 4. The formed azo compound 6 was differentiated from the solution in the form of a precipitate.

This research focuses on the synthesis of adamantane-containing dipeptides via multi-component Ugi reaction (Ugi 4CR). The modification of drugs with adamantane has shown to increase their lipophilicity and stability [1]. Due to the wide application in the pharmaceutical field, adamantine derivative compounds are receiving more attention. Ugi reaction provides a fairly simple procedure to synthesize peptides and, therefore, is a useful method in this regard. However, the possibility of a side reaction occurring is high which can pose a challenge during the purification process. In this experiment, Ugi four-component reaction (Ugi 4CR) was conducted by condensation of isobutyl aldehyde (1) with 1-amino-adamantane hydrochloride (2) in the presence of TEA in an ethanol area at 40˚C temperature. After formation of the medium, compound 3, benzoic acid (4) (reaction 1) or trifluoroacetic acid (5) (reaction 2) were added to the reaction mixture and, finally, while cooling in an ice bath ethyl isocyanoacetate (6) was added. The reaction was monitored by TLC (Ethyl acetate/Hexane ½ ration mixture). After 72 h stirring and heating, dichloromethane was added to the reaction mixture, and it was transferred to the separation funnel. It has been worked up with saturated NaHCO3 and washed with 1M KHSO4 solution. The organic phase was concentrated and chromatically purified on the column by the standard method (SiO2, petroleum/ethyl acetate), and dipeptides 7 and 8 were obtained with low yield.

Multicomponent reactions (MCR) are effective in comparison to two-component reactions since we are able to receive a huge variety of products from a very little amount of starting material. One of the MCR systems involves the interaction with isonitriles; Such MCR systems are widely used in the pharmaceutical industry. It is quite effective and versatile to yield low-molecular druglike compounds. One example of an MCR reaction is the Ugi reaction. Ugi reaction is a multicomponent reaction in organic chemistry. It includes four compounds: acids, aldehyde or ketone, amine, and isonitrile. Ugi reactions are important as they are efficient and useful tools to prepare different types of bonds and compounds, such as peptides, different natural products, and heterocyclic compounds. The prime focus of this research is to take action on the 1-amine-adamantane in the Ugi reaction. Adamantane is considered an interesting field of research due to its exceptional qualities. Adamantane derivatives are actively used pharmaceutical industry due to their durable properties. Its derivatives are powerful compounds in a wide range of applications from systemic to topical therapy In this research, the reaction of 1-amine-Adamantane (1), isobutyl aldehyde (2), 4- methoxy benzoic (4) acid and ethylisocyanoacetate (5) through the multicomponent Ugi reaction was conducted in the area of MeOH, at 40˚C temperature. The reaction mixture was stirred for 72 h. After finishing the reaction, the mixture was worked up with saturated NaHCO3 and washed with 1M KHSO4 solution. The organic phase was concentrated and chromatically purified on the column by the standard method (SiO2, petroleum/ethyl acetate), and the corresponding dipeptide was obtained.

Azo dyes are particular because of their physiochemical stability and optical properties, as well as their efficiency in the dyeing process. They have also been discovered to be involved in DNA inhibition and RNA synthesis in the cell. Apart from the dying properties that azo compounds possess, they also have antibacterial, antiviral, antifungal, and cytotoxic features. Azo-metal complexes have been found to be potent antibacterial agents against E. Coli and Staphylococcus aureus. In the biomedical field, they are used as drug carriers or in cellular staining, which helps create better images of metabolic processes in the cell. Azo dyes are actively utilized in hypnotic medicine for the treatment of insomnia. They also have high-tech applications in lasers and optical systems, as well as fuel cells. The most current development in the usage of azo compounds is in cancer diagnosis and therapy. The biological significance of azo compounds is still being investigated and their full potential in this regard has not been explored as of yet. In this research, the starting compound - 2,3,3-trimethyl-5-nitro-3H-indolenine (2) was synthesized by nitration of 2,3,3-trimethyl-3H-indolenine (1). The reduction of compound (2) was conducted using Sn/HCl at a high temperature. The diazotization of compound (3) was carried out using HNO2 in an acidic area and at low temperatures. N,N-diethylaniline (5) was added to the solution of diazonium salt (4). The formed azo compound (6) was separated out in the form of a precipitate. The quaternization of compound (6) with CH3I was performed in a shallow ampoule at 80-82 ˚C and the quaternized salt (7) was isolated.

Azo compounds are among the very applicable compounds in Organic chemistry. Their popularity has significantly grown over the last period. They have been used in fields such as cosmetics, clothing industry, and biomedicine etc [1,2]. Azo dyes are reported to have antibacterial, antifungal and antiviral properties. These traits make them suitable to be used in medicine. Other than that, they possess the drug carrier and drug like properties. Because of their coloring function, azo dyes are also used in cellular staining, this helps with visualization of cellular organelles and eases the study of metabolic processes. Apart from biomedical application, azo dyes are widely used in textile, leather, paint, etc, production. This paper focuses on the synthesis of bis-azo dyes on the base of 2.3.3.- trimethylindolennie, as well as its UV study. In this research, initially, nitration of 2,3,3-trimethyl-3H-indolenine (1) with the "mixed acid" at a molar ratio of 1:1.1:28 (compound 1−HNO3−H2SO4) was carried out and the mononitration product 2 was isolated in 85 % yield. Azo Compound 3 with a high yield was obtained by reduction of 2,3,3-trimethyl-5-nitro-3H-indolenine in the presence of NaBH4 in Methanol at room temperature. The analysis shows that during the interaction of NaBH4 with the nitro group the reduction of the pyrrole ring in the indolenine nucleus takes place, while the diazo group remains stable in the molecule. Which is well seen in the infrared (corresponding peak 3200 cm-1 ) and NMR spectrum. The substance has a yellow color.

Perspectives of spiropyrans to design new photo controlled molecular equipment and biological materials, logic valves and sensors are not exhausted. Therefore, today, active investigation to design and study compounds with new properties are underway [1]. Recently, carbon nanoparticles have occupied a large place in the scientific literature due to their unique electrical, thermal and other properties. The works appeared on photochromic compounds (spiro-compound and azo derivatives), which are combined with carbon nanoparticles and their use in technology is introduced due to their improved properties. Both sides of a two-dimensional graphene are p-p* electron clouds that are active electrophilic and nucleophilic substituents. The exposed flat conjugated dye will be interacting with the graphene-electronic system, which will adjust in features of spiropyranes such as time of interconverting, action of environmental factors, dipole moment, relaxation, etc. It is noteworthy that the spiropyranes are already used in biological materials. Graphene nanoparticle can be used as a container due to its large surface. For this purpose, it was selected to carry out synthesis and research of spirochromes containing azo dyes and then conduct their functionalization with graphene nanoparticles. A new azo- and spiro-group containing photochromic compound was synthesized according to the given scheme. Initially was synthesized starting compound - 5-nitro-2,3,3-trimethylindolenine (2) by nitration of 2.3.3-trimethylindolenine (1). The quaternization of the compound 2 with CH3I was performed in a shallow ampoule at 80-82 ˚C in the acetonitrile area and quarternized salt 3 was isolated. With further reduction of compound 3 with LiAlH4 in tetrahydrofuran compound 4 was formed. By the treatment of obtained compound 4 with alkaline solutions forms compound 5, which reacts with 5-nitro salicylic aldehyde and gives a compound 6, the maximum absorption of which in the alcohol area is 660 nm (the maximum absorption of similar spiropyranes is 540 nm).

It is known that benzimidazoles and adamantanes have high level of bioactivity and are used as drugs against variety of diseases and infection [1,2], therefore the synthesis of new derivatives of adamantane containing benzimidazoles and study their biological activity is interesting. The present work aims to synthesis some of new 5(6)-(1-adamantyl)-1H-2-R-benzimidazoles based on adamantyldiaminobenzene. For this purpose, cyclisation of 4-(1-adamantyl)-1,2-diaminobenzene dihydrochloride with some aromatic carboxylic acids and aldehydes were conducted according to the scheme.The condensation reaction of 4-(1-adamantyl)-1,2-diaminobenzene dihydrochloride (1) with carboxylic acids in PPA or POCl3 medium was conducted. It was found that by heating a mixture of compound 1 with aromatic acids (salicylic-, dibromo-, and diiodsalicylic-, 3- amino- and 4-amino benzoic acids) in a ratio of 1: 1, 1: 2 in the presence of PPA, the corresponding benzimidazoles 2, 5, 6 were isolated in different yields, but isolation of benzimidazole derivatives 3 and 4 with dibrom and diiodosalicylic acids under the same conditions failed, due to the grinding of the reaction mixture and the removal of iodine and bromine. Preparation of benzimidazoles 3, 4, 7 were possible by heating the reaction mixture in POCl3 medium (107°C). The condensation reaction of compound 1 with aromatic aldehydes was studied. By boiling the equimolarratios of diaminobenzene 1 and aldehyde (salicyl-, 3,5-dibromosalicyl-, 5-bromosalicyl-, 5-nitrosalicylaldehydes, 3-nitrobenz-, 4-nitrobenz-, 4-diethylaminobenzal-dehydes) in abs. alcohol and by oxidizing the obtained Schiff bases in nitrobenzene, the corresponding adamantylben zimidazoles 8-15 were synthesized in high yields.The molecular structure of the synthesized compounds was established by spectroscopy analysis, including IR, UV, 1 H, 13C NMR and HRMS. It is perspective to place the nanoparticles of synthesized compounds (2-15) on the polymer matrix to impart prolonged effects of biological activity. 

In the present study, the synthesis of adamantane moiety containing new dipeptide via isocyanide-based multicomponent reaction by using adamantane-1-carboxylic acid with an equimolar ratio of isobutyl aldehyde, glycine ethyl ester hydrochloride, and ethyl isocyanoacetate is described and the preparative method of the synthesis was worked up. By interaction of obtained dipeptide with hydrazine hydrate is formed corresponding hydrazide derivative. The hydrazide compound was then allowed to react with some aldehydes and acids forming the corresponding hydrazones and carbonyl hydrazides.

It is interesting to combine spiropyran with other photochromic compounds to maintain the important properties of both classes. For this purpose, we have selected a diazo group, which, after irradiation of the sample by incorporating the formed spiropyran conjugated chain, will cause (or lead to) a sharp change in the maximum absorption, which has been confirmed. We synthesized a new hybrid (azo and spiro) photochromic compound according to the given scheme. We first synthesized the starting compound - 5-nitro-2,3,3-trimethylindolenine (2) by nitration of 2,3,3-trimethylindolenine (1)[4]. With further reduction with LiAlH4, in the area of International Online Conference - 2020, Tbilisi, Georgia 26 absolute diethyl ether, at room temperature, was obtained compound 4with a high-yield (99%). Quaternization of the formed compound 4with CH3I was performed in a shallow ampoule at 80- 82˚C in the acetonitrile area and quarternized salt 5 was isolated. We obtained the same compound 5 in a second way, namely, we first conducted quaternation of compound 2 with CH3I at acetonitrile at 25-30 ˚C. With further reduction of compound 3 with LiAlH4 in the area of tetrahydrofuran compound, 5 is formed. By the treatment of obtained compound 5 with alkaline solutions forms compound 6, which reacts with 5-nitro salicylic aldehyde and gives a compound 7, the maximum absorption of which in the alcohol area is 660 nm (the maximum absorption of similar spiropyranes is 540 nm). Presumably, it represents spiropyrane.

Isocyanide-based Multicomponent Reactions (IMCR) like Ugi Reaction, are the most interesting to synthesize biologically active peptides and amides [1]. Ugi reaction involves condensation of four components: An aldehyde, an amine, an isocyanide, and an acid are condensed and quickly produce the main product. This 4-component reaction is productive to obtain the pseudo peptides, peptides and peptoids. Adamantine is a widely used compound in the synthesis and applications of new drug delivery systems and other numerous transformations [2] . The aim of our research work was to synthesize amino-1-adamantine containing dipeptides via Ugi-4-component reaction. Amino-1-adamantane (1), aldehydes (2), acids (3) and ethylisocya-noacetate (4) were chosen as starting materials for the IMCR (table 1). The reactions were conducted in the ethanol area at 35°C temperature and the mixture were stirred for 32h. Afterward CH2Cl2 was added quaked with saturated NaHCO3 and 1M KHSO4. The organic phase was concentrated and purified on the column. Dipeptides 5a-h, Passerini product 6, amides 7, and shiff bases 8 were obtained. 

Adamantane active group has proven its high membrane permeability through the path of its lipophilicity and symmetric geometry. Besides, it was shown that in most cases, attachment of adamantane group decreases toxicity and prolongs the activity of substances [1]. On the other hand, Benzimidazole is well-known for anti-viral, antimicrobial and fungicide capabilities. Our research combines the two active group and aims for enhanced biological activity [2]. Previously, we have synthesized 2-(1-adamantyl)-1H-benzimidazole derivatives and studied certain properties of them [3]. The aim of present work was to synthesis of N-alkylated 2- (1-adamantyl)-1H-benzimidazoles, 5(6)-amino-2-(1-adamantyl)-1H-benzimidazole and study some transformations. 2-(1-adamantyl)-1H-benzimidazole (1) in high yield (93%) was obtained by heating a mixture of 1-adamantanecarboxylic acid and o-phenylenediamine in POCl (Scheme 1). By interaction of alkyl halogens with compound 1 in the area of DMF in presence of KOH compound 2 and 3 was synthesized. The nitration reaction of compound 1 was carried out by using at a molar ratio of 1:28 HNO3/H2SO4 and compound 4 was isolated in high yield. 5(6)-amine-2-(1- Adamantyl)-1H-benzimidazole 5 was obtained by reduction of 5(6)-nitro-2-(1-adamantyl)-1H[1]benzimidazole (4) with molecular hydrogen in the presence of Raney Ni in alcohol area and by interaction of compound 5 with Benz aldehyde and 5-nitrobenzaldehyde corresponding Schiff bases 6 and 7 were isolated in high yields.

The remarkable structural and chemical properties of adamantane afford attractive opportunities to design various adamantane-based scaffolds for biomedical applications. Adamantane itself has a great lipophilic property which is greatly beneficial as it enables to its derivatives to hit specific target segments of cells. First of all, this property ensures that the adamantane derived drugs penetrate or bind the lipid bilayer quite well, in some cases incorporating selective binding to certain receptors and ion channels. Also, the lipophilic nature of adamantane prevents the metabolic cleavage of other functional groups which increases the drug’s overall activity, making it more effective and long lasting. Moreover, adamantane derivatives are also known for its biocompatibility, meaning they are not toxic. The human liver has the ability to digest these compounds, hence, the chances of drug accumulation in the living organism through the time should be minimal. Considering the activity of N-(1-adamantyl) carboxamides [1 & 2], we aimed to synthesize new derivatives of N-(1-adamantylcarbonyl)-ophenylenediamine according to the Scheme 1

Adamantyl-containing compounds have attracted many chemists’ attention due to their drastic influence on biological processes. They have shown antiviral, antibacterial, antifungal, anti-inflammatory and central nervous, and 11b-HSD1inhibitory activities. The lipophilicity of Adamantane changes ADME properties of molecule, binds a hydrophobic site in enzyme and acts as an inhibitor so, they are widely used in drug industry. These newly synthesized products contain not only Adamantane trace, but also a C-N double bond called imine or Schiff base. Schiff bases are active against a wide range of organisms since they play an important role in living organisms, such as decarboxylation, transamination and C-C bond cleavage. The aim of this research was to synthesize Adamantyl containing drug-like molecules which might have biological activity. Converting Adamantane carboxylic acid to ethyl Adamantane carboxylate was done by solving Adamantane carboxylic acid in absolute ethanol and adding thionyl chloride to the mixture dropwise in stirring condition during 3-4 hours. Secondly, by dropwise adding of hydrazine hydrate pure ester was converted to carbohydrazide. After completion of reaction and washing procedures, white sticky product was left. The reaction of carbohydrazide and following aromatic aldehydes in ethanol, produced corresponding Schiff bases. All reaction mixtures were washed using hexane through the Schott’s funnel. The range of yields of the reactions was between 75-85%. The final step of synthesis was to reduce the C-N double bond by reducing the agent Sodium borohydride. Two Schiff bases out of three were reduced and collected. The structures were confirmed by IR and 1H NMR spectroscopy.

Adamantane active group has proven its high membrane permeability through the path of its lipophilicity and symmetric geometry. Besides, it was shown that in most cases, attachment of the adamantane group decreases toxicity and prolongs the activity of substances [1]. On the other hand, Benzimidazole is well-known for its anti-viral, antimicrobial and fungicide capabilities. Our research combines the two active groups and aims for enhanced biological activity [2]. Previously, we synthesized 2-(1-adamantyl)-1H-benzimidazole derivatives and studied certain properties of them [3]. The aim of the present work was to synthesize N-alkylated 2- (1-adamantyl)-1H-benzimidazoles, 5(6)-amino-2-(1-adamantyl)-1H-benzimidazole and study some transformations. 2-(1-adamantyl)-1H-benzimidazole (1) in high yield (93%) was obtained by heating a mixture of 1-adamantane carboxylic acid and o-phenylenediamine in POCl (Scheme 1). By interaction of alkyl halogens with compound 1 in the area of DMF in presence of KOH compound, 2 and 3 were synthesized. The nitration reaction of compound 1 was carried out using a molar ratio of 1:28 HNO3/H2SO4 and compound 4 was isolated in high yield. 5(6)-amine-2-(1- Adamantyl)-1H-benzimidazole 5 was obtained by reduction of 5(6)-nitro-2-(1-adamantyl)-1H-benzimidazole (4) with molecular hydrogen in the presence of Raney Ni in alcohol area and by the interaction of compound 5 with Benz aldehyde and 5-nitrobenzaldehyde corresponding Schiff bases 6 and 7 were isolated in high yields. The structures were confirmed by IR and NMR spectroscopy.

Benzimidazole derivatives are characterized by various types of pharmacokinetic and pharmacodynamic properties. Benzimidazole nucleus is one of the bioactive heterocyclic compounds that exhibit a range of biological activities. The chemistry and pharmacology of adamantane derivatives have been of great interest because of their wide range of pharmacological properties. They amplify the energy of the human body and significantly improve the emotional and physical state of patients. Previously, we synthesized 2-(1-adamantyl) benzimidazole derivatives [1]. In the present study, the aim of our work was to synthesize a series of novel 5(6)-nitro-2-(1- adamantylmethyl) benzimidazole according to scheme 1. The condensation reaction of 5(6)-nitro-o-phenylenediamine with 1-adamantane acetic acid was conducted in presence of POCl3 at 1 h heating at 105-108°C temperature and of PPSE at 5 h heating at 160-163 °C. Compound 1 with a high yield was obtained. The interaction of alkyl halogens with 5(6)-nitro-2-(1-adamantylmethyl)-1H-benzimidazole (1) in the area of DMF in presence of KOH compounds 2 and 3 were synthesized. The reduction of compound 1 with molecular hydrogen in the presence of Raney Ni was carried out in the alcohol area and compound 4 was obtained with a 65% yield, in which interaction with 5-bromosalicylic-, 3,5-dibromosalicylic-, 5- nitro-salicylic-, 3-nitrobenzaldehyde in alcohol area by heating at 1-5 h was formed corresponding Schiff bases 5-8. Condensation of amine 4 with acetic anhydride to the formation of the corresponding acyl derivative 9 with a high yield. The structures were confirmed by IR and 1H NMR spectroscopy.

The target synthesis and study of adamantane nitrogen-containing new structures for viral and bacterial infection and against other biologic agents to create new effective means are perspective and actual. For this aim, the synthesis of high effective mebendazole (mebenvet, vermoxe) and albendazole drugs adamantane-containing analogs was realized. Particularly, the synthesis of new derivatives of 5(6)- benzoyl-2-(1-adamantyl)benzimidazoles, 5(6)-(1-adamantyl)-2-aminophenyl benzimidazoles, and benzoxazoles. 5(6)-benzoyl-2-(1-adamantyl)benzimidazoles were synthesized by interaction of 4- benzoyl-o-phenylenediamine dihydrochloride with adamantane-1-carbonyl chloride in abs. THF and the obtained compounds cyclization in POCl3 were performed. Also, by direct interaction of diamines with adamantane containing carboxylic acids in POCl3 and in the case of heating 3- acetylaminoadamantane-1-carboxylic acids in an oil bath in 225–250°C were obtained corresponding products. The synthesis of new derivatives of 5(6)-(1-adamantyl)-2-aminophenyl benzimidazoles was carried out by condensation 4-(1-adamantyl)-o-phenylenediamine dihydrochloride with aromatic aldehydes in acetonitrile in presence of hydrochloric acid and hydrogen peroxide at the room temperature, or by boiling in the area of absolute ethanol/nitrobenzene. Also 4-(1-adamantyl)- ophenylendiamines condensation reaction with p-aminobenzoic acid and p-acetylaminobenzoc acid in boiling polyphosphoric acid and polyphosphoric acid/xylene were carried out. The optimal conditions of the reaction were established, and the corresponding benzimidazoles were isolated. The synthesized nitro derivatives reduction and obtained amines acylation and condensation with aldehydes were studied. The corresponding amides and Shiff bases were obtained.

Geraniol (3,7-dimethyl-trans-2,6-octadiene-1-ol) and its cis-isomer nerol are valuable aromatic substances having subtle perfume of rose aroma and used in perfumery, also they are strategic raw materials – “building units” in syntheses of A, E and K vitamins, carotenoids, ionones and methyl-ionones. Commercial production of geraniol and nerol (up to 10 thousand tons annually) generally is based on the catalytic liquid-phase isomerization of linalool (3,7-dimethyl-1,6- octadiene-3-ol). Catalytic transformation of terpene alcohols include not only isomerization, but also their dehydratation, cyclization and condensation. These processes have been studied by us earlier for linalool [1], this report presents data on catalytic transformations of geraniol. The same micro-mesoporous catalysts synthesized by recrystallization of commercial BEA- zeolites in NaOH aqueous solutions and characterized by chemical composition, pore volumes and specific surface areas defined by nitrogen adsorption-desorption, and the acid properties estimated using temperature-programmed desorption of ammonia, have been used in experiments carried out in an atmosphere of nitrogen or argon in a liquid phase at 27–150°C. The analysis of products of catalytic transformations was carried out by the GCMS (Agilent Technologies, 5890B/5977A, capillary column HP-5ms, Ultra Inert, 30 m x 0.32 mm x 0.25 μm); the main products are β-linalool, trans-geraniol, trans,trans-farnesol and (2E,6E)-6,11-dimethyl-2,6,10-dodecatrien-1-ol, small quantities of β-mircene, D-limonene, trans-β-ocymene, β-ocymene, α-terpineol, nerol, cis-isogeraniol, trans,trans,trans geranylgeraniol, p-camphorene and unidentified isomer of trans-geranylgeraniol are present. It is established, that in “zeolitic reactor” it is possible to receive such large molecules as trans,trans-farnesol and (2E,6E)-6,11-dimethyl-2,6,10-dodecatrien1-ol at a relatively low temperature, by one-pot method and with selectivity up to 35 and 52%, respectively. 

Isocyanide-based Multicomponent Reactions (IMCR) like Ugi Reaction, are the most interesting to synthesize biologically active peptides and amides [1]. Ugi reaction involves condensation of four components: An aldehyde, an amine, an isocyanide, and an acid are condensed and quickly produce the main product. This 4-component reaction is productive to obtain the pseudo peptides, peptides and peptoids. Adamantine is a widely used compound in the synthesis and applications of new drug delivery systems and other numerous transformations [2] . The aim of our research work was to synthesize amino-1-adamantine containing dipeptides via Ugi-4-component reaction. Amino-1-adamantane (1), aldehydes (2), acids (3) and ethylisocya-noacetate (4) were chosen as starting materials for the IMCR (table 1). The reactions were conducted in the ethanol area at 35°C temperature and the mixture were stirred for 32h. Afterward CH2Cl2 was added quaked with saturated NaHCO3 and 1M KHSO4. The organic phase was concentrated and purified on the column. Dipeptides 5a-h, Passerini product 6, amides 7, and shiff bases 8 were obtained. 

The synthesis of new derivatives of 5(6)- benzoyl-2-(1-adamantyl)benzimidazoles, 5(6)-(1-adamantyl)-2-aminophenyl benzimidazoles, and benzoxazoles were conducted. 5(6)-benzoyl-2-(1-adamantyl)benzimidazoles were synthesized by interaction of 4- benzoyl-o-phenylene-diamine dihydrochloride with adamantane-1-carbonyl chloride in abs. THF and the obtained compounds cyclization was done in POCl3. Also, that product was obtained by direct interaction of diamines with adamantane containing carboxylic acids in boiling POCl3 and in the case of 3- acetylaminoadamantane-1-carboxylic acids by heating in an oil bath at 225–250°C. The synthesis of new derivatives of 5(6)-(1-adamantyl)-2-aminophenyl benzimidazoles was carried out by condensation 4-(1-adamantyl)-o-phenylenediamine dihydrochloride with aromatic aldehydes in acetonitrile in presence of hydrochloric acid and hydrogen peroxide, or in absolute ethanol/nitrobenzene. Also 4-(1-adamantyl)- o-phenylendiamines condensation reaction with p-aminobenzoic acid and p-acetylaminobenzoc acid in polyphosphoric acid and polyphosphoric acid/xylene were carried out. The optimal conditions of the reaction were established, and the corresponding benzimidazoles were isolated. The synthesized nitro derivatives reduction and obtained amines acylation were studied. The corresponding products were obtained.

The aim of the present work was the synthesis of 2-(1-adamantyl)-1H-benzimidazoles and some adamantine-containing dipeptides . It is known that 2-(1-adamantyl)-1H-benzimidazole (1) is not formed by heating of o-phenylenediamine with 1-adamantane carboxylic acid either in polyphosphoric acid or its ethyl ester or in aqueous hydrochloric acid at atmospheric pressure. 2-(1-Adamantyl)-1H-benzimidazole (1) was obtained by heating o-phenylenediamine with 1- adamantane carboxylic acid in a POCl3 medium in 93% yield. Nitration of 2-(1-adamantyl)-1H-benzimidazole (1) with the "nitration mixed acid" was carried out employing different ratios of the reactants. At a molar ratio of 1:1.1:28 (compound 1 : HNO3:H2SO4), the mononitration product 2 was isolated in 92% yield, whereas at a ratio of 1:10:56 (compound 1: HNO3:H2SO4) the dinitration product 3 was obtained in 81% yield. 2-(1-Adamantyl)-1H-benzimidazol- 5(6)-amine (4) was obtained by reduction of 2-(1-adamantyl)-5(6)-nitro-1H-benzimidazole (2) with hydrazine hydrate or molecular hydrogen in the presence of Raney Ni in alcohol. To prepare new derivatives of 2-(1-adamantyl)-1H-benzimidazole, the condensation of amine 4 with salicylaldehyde, 5-bromo-, 5-nitro-, 5-nitro-salicyl- and 3,5-dibromosalicylaldehyde was carried out by heating in an alcohol solution for 1-3 hours. The corresponding Schiff bases 6-10 were isolated in high yields. Condensation of amine 4 with 1-adamantanecarbonyl chloride, Acetic acid anhydride, salicylic acid chloride, 4-benzamidobenzoic acid chloride and benzoyl chloride in the absolute ether in the presence of TEA, or by the Schotten-Baumann method in benzene or toluene in the presence of 10% aqueous NaOH led to the formation of the corresponding novel 2-(1-adamantyl)-1H-benzimidazol-5(6)-amine acyl derivatives 11-15. Some adamantane-fragment containing dipeptides were synthesized on the basis of isocyanides via Ugi reaction. Adamantane-1-carboxylic acid, different aryl- and alkyl amines, aldehydes and adamantane-2-on, ethyl isocyanoacetate and benzene isocyanide are used as reacting components. Ugi-reaction was carried out in ethanol at different temperatures and the following structures of dipeptides (1, 2) were obtained.

The adamantane derivatives are characterised by diverse biological activity including but not limited to antiviral, antimicrobial, anticarcinogenic, anti-cataleptic, immunotropic, neuro-psychotropic activities. 35 compounds (adamantane derivatives (N-adamantylanilides, 4-(1-adamantyl)anilides, adamantylbenzimidazoles) and analogues of salicylanilides) were synthesized by us in order to reveal prospective antiviral, antibacterial and anthelminthic agents. The synthesized compounds were investigated against different Gram positive and Gram negative bacteria and virus strains in collaboration with U.S. Army Medical Research Institute of Infectious Diseases (USAMRIID, S. Bavari, R. Panchal). The different bacterial species and strains used in this study include Bacillus anthracis (Sterne), B. anthracis (Ames), Staphylococcus aureus ATCC 29213, MRSA 1094, F. tularensis (Schu4), F. novicida. Mycobacteria smegmatis ATCC 19420, Escherichia coli ATCC 25922, Acenitobacter baumanii complex, Klebsiella pneumoniae 5657, Pseudomonas aeruginosa PA01, Yersinia pestis CO92, Y. pestis (pgmpST-), Burkholderia mallei ATCC 3344, B. pseudomallei DD503, B. thailandensis, and B. cepacia . The minimum inhibitory concentration (MIC) was determined by the broth microdilution method [4]. Several adamantane derivatives showed broad-spectrum antibacterial activity. The different viral strains used for the study included the recombinant Zaire Ebola virus (EBOV) engineered to express the enhanced GFP (EBOV-eGFP), Marburg Ci67 (MARV) Venezuelan equine encephalitis virus (VEE), Eastern equine encephalitis virus (EEE) FL91, Rift Valley fever virus (RVFV) ZH501 and Crimean-Congo haemorrhagic fever (CCHF) [5]. The adamantane derivatives were tested at a single concentration of 20 µM against different virus families namely Filoviruses (EBOV, MARV), Bunyaviruses (Rift valley fever virus and Crimean-Congo haemorrhagic fever virus) and alphaviruses (Venezuelan equine encephalitis virus and Eastern equine encephalitis virus). Several adamantane derivatives exhibited a broad-spectrum antiviral activity. However, several of the identified hit compounds were also toxic to the cells as measured by the eduction in cell number in our high-content imaging assays. 

It is known that benzimidazole derivatives characterize wide spectrum biological activity. Furthermore, it has been experimentally found that the introduction of the adamantane fragment into the molecule of medication enhances its bioactivity and reduces its toxicity. Therefore, adamantine-containing benzimidazoles are interesting in the search for new medications. The aim of the present work was to find the improved method and the optimal conditions for the synthesis of 2-(1-adamantyl)-1H-benzimidazole and study some of its transformations [1]. In this direction 2-(1-Adamantyl)-1H-benzimidazole has been synthesized, and its nitration and following reduction have been carried out. By condensation of the obtained 2-(1-adamantyl)-1H-benzimidazole-5(6)-amine with aromatic aldehydes and acyl chlorides, the corresponding novel Schiff bases and amides have been accessed. Some of 2-(1-adamantyl)-N-alkylated- benzimidazoles have been synthesized.

        It is known that adamantane derivatives are characterized by biological activity. Highly effective active substances are used in medicine. Furthermore, it has been experimentally found that the introduction of the adamantane fragment into the molecule of an active substance enhances its bioactivity and generally reduces toxicity. Also, benzimidazole derivatives are known as biological activity compounds. They are used in medicine, and veterinary medicine. Therefore, adamantine-containing benzimidazoles are of interest from the viewpoint of searching for new compounds with a broad spectrum of pharmacological action. As well known, peptides are biologically active substances, which are presented in all living cells of organisms. They participate in and control a lot of biochemical and physiological processes. Because of a wide spectrum of activity of adamantanе fragment-containing compounds, adamantane derivatives were used in the synthesis of peptides, and their biological activities were studied. At the same time, adamantane-containing peptides synthesized based on isocyanides by multicomponent reactions are not adequately studied. Issues from this we were interested in the study of synthesis and biological activity of adamantane fragment containing peptides via Ugi reaction based on isocyanide. The aim of present work was the synthesis of 2-(1-adamantyl)-1H-benzimidazoles [4] and some of adamantine-containing dipeptides . 2-(1-Adamantyl)-1H-benzimidazole (1) was obtained by heating o-phenylenediamine with 1- adamantane carboxylic acid in a POCl3 medium in 93% yield. Nitration of 2-(1-adamantyl)-1H-benzimidazole (1) with the "nitration mixed acid" was carried out and the mono nitro product 2 was isolated in 92% yield. 2-(1-Adamantyl)-1H-benzimidazol- 5(6)-amine (4) was obtained by reduction of 2-(1-adamantyl)-5(6)-nitro-1H-benzimidazole (2). To prepare new derivatives of 2-(1-adamantyl)-1H-benzimidazole, the condensation of amine 4 with several aldehydes was carried and corresponding Schiff bases 6-10 were isolated in high yields. Condensation of amine 4 with several led to the formation of the corresponding novel 2-(1-adamantyl)-1H-benzimidazol-5(6)-amine acyl derivatives

Antimicrobial drugs or chemicals are the substances used to kill or slow down the growth of microorganisms. They include antibiotics, antiviral, antifungal, and anti-parasitic agents. The biological activity of the compounds depends on the structure of the molecule. Benzimidazole is one such compound, which attracts the attention of synthetic chemists for the synthesis of antimicrobial drugs. This compound has various applications in several fields. Benzimidazole plays an important role in various medicines. This stimulated great interest in the structural study of Benzimidazole and related compounds and much success was made in the pharmacetical industry. Some commercially used Benzimidazole based drugs are: Azomycin, Metronidazole, Benomyl, Clemizole, Enviroxime, Irtemazole, Astemizole, Omeprazole, Pentoprazole, Thiabendazole and Nocodazole. It shows a wide spectrum of biological and pharmacological properties such as antifungal, antimicrobial , anthelmintic, antiviral, topoisomerase inhibition and anticancer activities. On the other hand, several compounds of this group have revealed their teratogenic, embryotoxicity and other side effects. It is expected that if the carbamate group (-NHCOOR) is changed by lipophilic, hydrophobic, membranotropic and immunotropic adamantane pharmacophore will eliminate these negative effects and improve the biological characteristics of the molecule. Hence the search for novel biologically active compounds through the synthesis of adamantane-containing benzimidazoles and a study of their physicochemical and biological properties is a very timely scientific task. Thus, we may state that synthesis and analysis of new derivatives of adamantane containing benzimidazoles for the creation of prophylactic and therapeutic medications that meet the modern requests are perspective and actual. For this aim the synthesis and reactions of 5(6)-(1–adamantyl)benzimidazoles were studied and previously reported. The following work is connected to the syntheses and research of new 2-(1-adamantyl)benzimidazoles. For this goal some adamantane ring containing benzimidazole derivatives (a, b, c) were synthesized by us

Adamantyl-containing compounds are utilized for a number of applications in medicinal chemistry (Amantadine, Rimantadine, Paramantine,Protexin,Bromantane, Kemantaneand many others are used widely in medicine). The adamantane derivatives are characterized by antiviral, antimicrobial, anticancerogenic, anticataleptic, immunotropic, neuro-psychotropic, and other activities. The adamantyl group is present in seven compounds in current clinical use for the treatment of neurodegenerative disorders, viral infections, and type 2 diabetes, and in many more substances that are in development as potential therapeutics. In many cases, the adamantly group has been found to improve the pharmacological properties of a parent compound, without increasing its toxicity. On the other hand, dipeptides are characterized by a wide range of biological activities and are widely used in the drug industry [3]. It is known a lot of synthetic methods to obtain Peptides, but developments of isocyanides-based multicomponent reactions are more interesting [4-6]. In that way, the adamantane-containing peptides which are obtained via Ugi-reaction are less studied. Therefore, new developments for the synthesis of adamantane containing new peptides and the study of its properties are of great interest. The aim of the research is to synthesize adamantane containing new dipeptides by using 1-aminoadamantane, adamantan-2-one and adamantan-1-carboxylic acid, in which 1-3 structure was obtained. The structure of the obtained products was established by NMR spectral data.

Adamantane fragment containing organic compounds possess antiviral, antibacterial, anticancer, anticataleptic, immunotropic, neuro-psychotropic and other activities. They amplify the energy of the human body and significantly improve emotional and physical state in patients. Introduction of adamantane fragment into the molecule of a preparation changes or partly increases its biological activity, in most the cases reduces toxicity, which can be explained by the spatial structure of the compound, hydrophobia and lipophilicity. Also, suitable conditions of transportation into the biological membranes, prolongation effect of preparations, high immunotropicity and others can be considered. The aim of the research work is the development of a synthetic method for adamantane-fragment containing some benzylidenes, benzimidazoles and dipeptides. Studying the effects of electron donor adamantane on reaction capacity and specific biological activity of obtained adamantane-containing compounds. We aimed to synthesize new derivatives of o-phenylenediamine in the molecule with adamantane-1-carboxamide (Ad−CONH) and arylidenimine (Ar−CH=N) groups. 2-(1-Adamantyl)benzimidazole (9) was synthesized with a high yield. Afterward, by nitration of 9 and reduction of 10 was formed compound 11. Some of the new corresponding amides 12-14 were obtained by the interaction of 5(6)-amino-2-(1-adamantyl)benzimidazole (11) with carboxylic acid chlorides and the condensation of 11 with aromatic aldehydes gave new Schiff bases 15-18. The Ugi four-component reaction (Ugi 4CR) was conducted by condensation of aldehyde or adamantane-2-on, amine, adamantane-1-carboxylic acid, and isocyanide at 0-60 °C on the ethanol medium. Dipeptides 19 a-h and 20 a,b was obtained with a 42 – 64 % yield [7]. The structure of some synthesized compounds was determined by IR, 1 H NMR, and 13C NMR spectral data.

Multicomponent coupling reactions are a powerful method for the construction of a diverse collection of small molecules as a source for biologically interesting compounds. The Ugi four-component coupling reaction is represented among this class of reactions. The Ugi reaction is a coupling reaction between aldehyde, amine, isocyanide, and carboxylic acid to give dipeptides in one step.  It is known a lot of synthetic methods to obtain Peptides, but developments in isocyanide-based multicomponent reactions are more interesting [1]. In that way the bioactive adamantane-containing peptides which are obtained via Ugi-reaction are less studied [2]. Therefore, new developments for the synthesis of adamantane containing new peptides and the study of its properties are of great interest. The aim of our research were to synthesis of adamantane containing new dipeptides by using aminoadamantane, adamantanone and adamantane carbocylic acide. The structure of the products was established by   NMR and Mass-spectra data.

Substances with an adamantane fragment in the molecule have a broad spectrum of biological activity. For this aim we synthesized 2- and 5(6)-(1-adamantyl)benzimidazole derivatives. The synthesized adamantylbenzimidazoles were assayed for their biocide, antihelmintic, antitumor, and anti-HIV activity revealing compounds with identified activity [3, 4]. For the prognosis of probable activities of adamantane-containing benzimidazoles, we provided virtual screening by online program www.Pharmaexpert/passonline/ which has shown that adamantylbenzimidazole are with high probability expected to have the following effects in the experiment: Antiviral (Influenza, Picornavirus, Adenovirus); Anthelmintic; Antineoplastic (brain cancer); Antiparkinsonian; Cytostatic; Nootropic; Urologic disorders treatment and other activities. 

The synthesis of some of the adamantane-containing new benzimidazoles by the following structure (a, b, c) has already been published [1,2]. Now here are presented some of the synthesized compounds NMR studies.  The NMR (1HNMR and 13CNMR) research was carried out at the institute of organic chemistry, at Saarland University, Germany.  It is known that in the 1HNMR spectrum of the CH2 protons of adamantane are characterized by signals in the region 1.58‐1.18 ppm, and CH Protons‐ in the regions of 1.96 ppm. The study of our synthesized compounds has shown that the CH2 and CH protons of the adamantane have been shown signals in the field of 2.099 ‐1.71 ppm In the compounds (1‐7), which is explained by the influence of the electron acceptor ring of benzimidazole. By the influence of the adamantane ring, the signals of the aromatic protons are displayed at 8.428‐7.077 ppm in compounds 2,5, and 7, and the signals of the aromatic protons are observed in the field 7.87‐6.52 ppm in the compounds 1,3,4 and 6. The 13CNMR research has shown that the signals of carbon atoms were displayed in the field 40.85‐27.29 ppm. in the compounds 1‐7. The report will be presented the NMR spectral data and theoretical calculation of NMR by a computer program,,Chem Draw Ultra 10.0'' and will be explained the influence of the substituted group in the benzimidazole and adamantine ring.

Peptides play a crucial role in fundamental physiological and biochemical functions of life. For decades now, peptide research is a continuously growing field of science.  Peptides (proteins) are present in every living cell and possess a variety of biochemical activities. They appear as enzymes, hormones, antibiotics, receptors, etc. Synthetic peptides may be useful in structure‐function studies of polypeptides, as peptide hormones and hormone analogs, in the preparation of cross‐reacting antibodies, and in the design of novel enzymes.[1] It is known that The adamantine line organic compound because of a wide spectrum of pharmacological activity is used widely in the medicine and the presence of adamantane radicals in molecules of medicinal preparations, enhances their activity and depresses the toxicity It is known a lot of synthetic methods to obtain Peptides, but developments in isocyanide based multicomponent reactions is more interesting [2]. In that way, the adamantane-containing peptides which are obtained via Ugi‐reaction are less studied [3]. Therefore, new developments for the synthesis of adamantane containing new peptides and the study of its properties are of great interest.  The aim of the research is to synthesize adamantane containing new dipeptides by using aminoadamantane, adamantanone, and adamantane carboxylic acid, in which the structure of dipeptides was obtained. The structure of the products was established by NMR and Mass‐spectra data.  

             It is known that the adamantane ring containing organic compounds is used widely in medicine (Amantadine, Rimantadine, Paramantine, Protexin, Bromantane, Kemantane, and many others) because of the wide spectrum of pharmacological activities. The adamantane derivatives are characterized by antiviral, antimicrobial, anticancero­genic, anticataleptic, immunotropic, neuro-psychotropic, and other activities. On the other hand, dipeptides are characterized by a wide range of biological activities and are widely used in the drug industry. it Is known a lot of synthetic methods to obtain Peptides, but developments in isocyanide-based multicomponent reactions are more interesting. In that way, the adamantane-containing peptides which are obtained via Ugi-reaction are less studied. Therefore, new developments for the synthesis of adamantane containing new peptides and the study of its properties are of great interest. The aim of the research is to synthesis of adamantane containing new dipeptides by using aminoadamantane, adamantanone and adamantane carbocylic acide, in which 1-2 structure was obtained. The structure of the products was established by   NMR and Mass-spectra data.  

The aim of this work was to synthesize the new derivatives of 5(6)-amino-2-(1-adamantyl)-benzimidazole. It is known that o-phenylenediamine does not react with adamantane-1-carboxylic acid and does not give adamantylbenzimidazoles. By us, this reaction was fulfilled by the interaction of o-phenylenediamine with adamantyl-1-carboxylic acid in presence of POCl3 at 1 hour boiling, And the corresponding cyclized product 2-(1-adamantyl)benzimidazole with 85% yield was obtained. The nitration was performed using a nitration agent (HNO3/H2SO4, 1:2,5) and the corresponding nitro-product with 88% yield was obtained, in which catalytic reduction with molecular hydrogen in absolute alcohol at room temperate in the presence of Raney nickel was isolated 5(6)-amino-2-(1-adamantyl)benzimidazole (4). The structure of synthesized compounds was established by IR and NMR spectrum analysis.

The presented work is dedicated to the synthesis of a new derivative of adamantanbenzimidazoles, namely the synthesis of 2-, 5 (6) -diamantan substituted benzimidazoles. The study of 3-acetylaminoadamantan-1-carbonic acid (1), 3- (p-acetylamy-nophenyl) adamantan-1-carbonic acid (2), 3-aminoadamantan-1-carbonic acid (3) and 3- (p-aminophenyl) adamantan- Condensation of 1-carbonic acid (4) [7] with 4– (1-adamantyl) -O-phenylenediamine (5) [8] dihydrochloride, the corresponding benzimidazoles 6-9 were synthesized (Scheme 1)

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