Novel spiroheterocycles containing a 1,3,4-thiadiazole unit: Synthesis and spectroscopic characterization

Abstract

We describe the preparation of a series of novel spiroheterocycles, namely 1,3,4-thiadiazole derivatives possessing an indane unit. These active heterocyclic compounds are prepared starting from thiocarbohydrazide and 2-indanone via an intermediate indan-2-thiocarbohydrazone which is used to afford the corresponding 2-(1-acetylhydrazino)-4H-acetyl-5-spiro(indano-2-yl)-1,3,4-thiadiazoline in an acidic medium. The 1,3,4-thiadiazole derivatives are obtained in good yields by reaction with aromatic carboxylic acids at reflux temperature in the presence of POCl3 as a catalyst, their structure–activity relationships are discussed and the structures of the newly synthesized derivatives are confirmed by spectroscopic techniques.