NATURAL SCIENCES

Journal of fundamental
and
applied researches

HETEROCYCLIZATION REACTIONS OF NITROACETONITRILES AND THEIR STRUCTURAL ANALOGS

2017. №2, pp. 110-132

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

In the review there were systematized and critically considered the data collected for the last decades on the synthesis of azaheterocyclic compounds produced by the reactions of 1,3-dipolar cycloaddition of the substituted nitroacetonitriles and their structural analogs containing electron-accepting groups (nitrate ester and nitrile groups, halogen, 1,2,4-oxadiazol, 1,2,3-and 1,2,4-triazole cycles) as well as of the conjugated cyanoethenes (dicyano- and nitrocyanoethenes) to various 1,3 dipoles (to diazoalkanes, nitrile imines, nitrile ylides, isochinoline bromides, nitrile oxides, organic azides). There were shown the perspectives of three-component heterocyclization reactions that enable to synthesize azaheterocyclic compounds of complex structure in one stage. Depending on the conditions in which these reactions are carried out, they are shown to produce pyrazines, pyrasols, izoxazolines, 1,2,3- and 1,2,4-triazoles, pyrrolidines, pyrrolisines, izoxazolines, furoxanes, izoxazols, aziridines and other compounds. The synthetic potential of cycloaddition products (including the reactions of hydroxymethylation, nitromethylation, hydrosonolysis, functionalization with azaheterocycles, reactions of acid and alkaline hydrolysis) are considered. The areas of their practical application are specified along with the perspectives of their further investigation. The synthesized products are shown to possess antimicrobic, antifungal, fungicidal, antimycobacterial, insecticidal, growth-regulating, hypertensive activities as well as they are sedative agents.

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