Synthesis of 2-Methyl-l-phenylthiocarbamoylglyoxal Arylhydrazones and Diethyl(arylazo)(phenylthiocarbamoyl)malonate and their Reactions with Hydrazines

Abstract

Abstract Treatment of a-phenylthiocarbamoyl acetyl acetone (1) with aromatic diazonium salts effects acetyl cleavage with the formation of 2-methyl-I-phenylthiocarbamoylglyoxal arylhydrazones (2a-c), which afford the anilinopyrazoles (5a-c) and the phenylimino-2- pyrazolines (6a-c) on treatment with hydrazine or phenyl hydrazine respectively. Treatment of diethyl a-phenylthiocarbamoyl malonate with aryl diazonium salts gave diethyl (arylazo)(phenylthiocarbamoyl) malonate which afford the 7-phenyl-5-(arylazo)- 2,3,7-triazabicyclo[3,2,0]hept-I-ene-4,6-dione (9a, b) and its 3-phenyl derivatives (9c, d) with hydrazines and phenyl hydrazine respectively