Journal of fundamental
applied researches

Synthesis of azaheterocyclic compoundsthe 1,3-dipolar cycloaddition

2013. 2, pp. 147-168

Makhommed Akhmed Abdelrakhim - post-granduate student, Astrakhan Stat University, 1Schaumyn Sq., Astrakhan, 414000, Russian Federation,

In mini review authors 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 of domestic and foreign literature of the last decades.

Key words: substituted nitroacetonitryl,1,3-dipoles,diazacompounds,nitril oxides,nitrilimines,nitrililides,azides,1,3-dipolar addition,biology activity,industrial toxicants