CHLOROACETONITRILE IN HETERO CYCLIC SYNTHESIS; NOVEL ROUTE FOR THE SYNTHESIS OF THIAZOLIDINE, CHORMENE, PYRROLE, AND PYRAZOLE DERIVATIVES AS ANTIMICROBIAL AGENTS

Abstract

Thiazolidinone (5b), chormeno [2,3-b] pyrrole (11) and 2-(2-ethoxyphenylamino) acetonitrile (16), were obtained from the reaction of chloroacetonitrile (1) with thioglycollic acid (2) , salicyaldehyde in presence of malononitrile, and o-phentidine ,respectively. Fusion of compound (5b) with hydrazine hydrate furnished (6), while fusion chloroacetonitrile (1), 2-chlorobenzaldehyde and thioglycollic acid (2) gave (8). Treatment of (1), and (16) with a mixture of aromatic aldehyde and hydrazine hydrate gave the corresponding Pyrazole derivatives (18,24,and 25). The reaction of compound (11) with each of acetic anhydride, carbon disulphide, and formic acid gave the corresponding chormeno [2,3-b] pyrrole derivatives(13-15),respectively. Refluxing (16) with salicyaldehyde in presence of ammonium acetate afforded- N-(2-ethoxyphenyl)-2-imino-2H-chromen -3-amine (19) .The novel pyrrole derivative (20) was obtained through reaction of (16) with a mixture of 2-chlorobenzaldehyde and malononitrile.