Synthesis and biological activities of 3-hydroxy-5-(2 ',5 '-disubstituted indol-3 '-yl)-1,2,4-triazoles and 4-acetyl-2-acetylamino-5-(2 ',5 '-disubstituted indol-3 '-yl)-1,3,4-thiadiazolines

Abstract

2,5-Disubstituted indol-3-carboxaldehydes (1a-d) were condensed with semicarbazide and thiosemicarbazide in ethanol and catalytic amount of glacial acetic acid under reflux conditions, afforded semicarbazones (2a-d) and thiosemicarbazones (4a-d), respectively. The semicarbazones (2a-d) on reaction with ferric chloride hexahydrate in ethanol produced 3-hydioxy-5-(2',5'-disubstituted indol-3'-yl)-1,2,4-triazoles (3a-d). When thiosemicarbazones(4a-d) were heated under reflux for 4 h with acetic anhydrate these gave 4-acetyl-2-acetylamino-5-(2',5'-disubstituted indol-3'-yl)-1,3,4-thiadiazolines (5a-d). The newly synthesised compounds were confirmed on the basis of analytical and spectral data. All the compounds were screened for their antimicrobial and anthelmintic activities.