NATURAL SCIENCES

Journal of fundamental
and
applied researches

REACTION 1,3-DIPOLAR CYCLOADDITION - A SYNTHESIS OF HETEROCYCLIC COMPOUNDS

2016. №3, pp. 86-106

Shustova Ekaterina A. - postgraduate student, Astrakhan StatРµ University, 1 Schaumyna Sq., Astrakhan, 414000, Russian Federation, tyrkov@rambler.ru

In mini review systematically and critically examined data, which collected over the past decade in the field of synthesis of azaheterocyclic compounds using the reactions of 1,3-dipolar cycloaddition of substituted nitroacetonitriles containing electron-withdrawing groups (nitro, ester, nitrile group, halogen, 1,2,4-oxadiazole, 1,2,3 - and 1,2,4-triazole rings) and conjugated cyanoethene (dicyano-and cyanonitroethene) to various 1,3-dipoles (diazoalkanes, nitrile imines, nitrile ylides, isoquinoline bromide, nitriles oxides, organic azides). Shown the prospects of three-component heterocyclization reactions, which allowing a one-step design of complicated azaheterocyclic compounds. Found that the products of these reactions, depending on the conditions of their implementation are pyrazines, pyrazoles, isoxazolines, 1,2,3- and 1,2,4-triazoles, pyrrolidines, pyrrolysine, isoxazolines, furoxan, isoxazoles, aziridines and other compounds. Analyzed synthetic possibilities of cycloaddition products (hydroxymethylation reaction, nitromethylation, hydrazonolysis, azaheterocycles functionalization, reactions of acid and alkaline hydrolysis), are opened fields of their practical applications and prospects for further researches are defined. It is shown that the desired products have antimicrobial, antifungal, fungicidal, antimycobacterial, insecticidal, growth-regulating, hypertensive activity and sedatives. Bibliography-113 primary sources.

Key words: замещенные нитроацетонитрилы, 1, 3-диполи, диазосоединения, окиси нитрилов, нитрилимины, нитрилилиды, азиды, 1, 3-диполярное циклоприсоединение, азагетероциклические соединения, биологическая активность, substituted nitroacetonitryl, 1, 3-dipoles, diazaco