Synthesis and Antimicrobial Activity of Polyfunctionally Substituted Heterocyclic Compounds Derived from 5‐Cinnamoylamino‐2‐Cyanomethyl‐1,3,4‐Thiadiazole

Abstract

Cinnamoyl isothiocyanate 1 was reacted with 2‐cyanoethanoic acid hydrazide 2 to afford 1‐cyanoacetyl‐4‐substituted thiosemicarbazide 3, which on treatment with a mixture of glacial acetic acid and acetic anhydride gave the desired 5‐cinnamoylamino‐2‐cyanomethyl‐1,3,4‐thiadiazole 4 . Compound 4 was subjected to react with aromatic aldehydes, phenylisothiocyanate, carbon disulphide, and arylidene malononitrile to give coumarin 5 , thiazolidines 8 , 9, and 1,3,4‐thiadiazolo[3,2‐a]pyridine 13 derivatives. The structures of all synthesized compounds were ascertained by spectral and analytical data. Antimicrobial activity of some of prepared compounds was investigated, and compounds 7, 8 were found to exhibit the highest strength.