NATURAL SCIENCES

Journal of fundamental
and
applied researches

Synthesis of functional substituted n-arylcarbanates and their transformations

2013. №4, pp. 126-148

Ionova Valentina A. - post-graduate student, Astrakhan State University, 1 Shaumyan Sq., Astrakhan, 414000, Russian Federation, valentinka86@yahoo.com

The results of synthesis of functionally substituted N-aryl carbamates and their use in the preparation of new aryl- and hetaryl-carbamates are summarized i1n mini-review. The prospects of use of N-nitroso-alkyl-N-aryl carbamates, amino, chloromethyl, hydroxy, acyl derivatives in the synthesis of 1,2-oxazine, indole, benzimidazole, 1,4-benzoxazine chromene, dihydrocoumarin, azetidine , thiazolidinone, 1,2,3-selenadiazole, 1,2,3-thiadiazole carbamate derivatives, spiro compounds with various heterocyclic moieties, and other biologically active compounds are shown. Reaction of methyl-N-(4-acetylphenyl) carbamate semicarbazone with selenium dioxide in acetic acid and thionylchloride receives corresponding 1,2,3-selenadiazole and 1,2,3-thiadiazole derivatives with a phenylcarbamate fragment. By refluxing of methyl-N-(4-acetylphenyl)carbamate thiosemicarbazone with chloroacetic acid, phenacylbromide in ethanol at the presence of АсОNa, and also with acetic anhydride are received thiazole and thiadiazole derivatives. The regularities of acyl substituted of methyl-N-phenylcarbamate condensations with isatin are explored and are founded that, in the case of meta-and para-substituted compounds corresponding indolinone chalcones are convenient key in synthesis of new compounds. Condensation of methyl (2-acetylphenyl)carbamate with isatin in similar conditions is accompanied by heterocyclization with formation of the methyl ester of 2,4t-dioxo-1,2,3-,44-tetrahydro-11Н-spiro[indole-3,2[-quinoline]-1--carboxylic acid. The efficiency of three-component condensation and ionic liquids in the synthesis of polyfunctional heterocyclic compounds is shown. It is found that L-proline is effective organocatalyst in the reaction of indolinone chalcone with azomethine providing regiospecific cycloaddition. Among of the synthesized aryl and hetarylcarbamates are founded substances exhibiting antimicrobial, antifungal, cardiovascular, anti-tuberculosis and protivoleproznuyu activity.

Key words: N-arylcarbamates,aromatic electrophilic substitution reactions,nitration,nitrosation,chloromethylation,condensation reactions,ring closure reactions involving carbamate and some other groups,hetarylcarbamates,reactions of carbamate group,heterocyclization