Chemoselective reaction of indole 1,3-dicarboxylates towards hydrazine hydrate:Bisheterocycles:Synthesis and antimicrobial activity of some new 2-methyl-3- ethoxycarbonyl-1-oxadiazolyl/thiazolidinonyl/pyrrolyl-aminocarbonylmethylindoles

摘要

Chemoselectivity of 1-ester over C_3-ester of the indole dicarboxylates 3a,b towards the nucleophilic attack of hydrazine hydrate has been evidenced by the exclusive formation of l-hydrazinocarbonylmelhyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 5a,b which have been further reacted separately with CS_2/KOH,p-chlorobenzaldehyde and acetonyl acetone to furnish the l-(5-mei-capto-l,3,4-oxadiazol-2-yl)metliyl-3-etlioxycaitonyl-5-substituted-2-metliylindoles 6a,b,1-p-Chlorobenzyl-idenehydrazinocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 7a,b and l-(2,5-dimethylpyrrol-l-yl)-aminocait)onylmethyl-3-ethoxycarbonyll-5-substituted-2-methylindoles 8a,b respectively.The Schiffs bases 7a,b are reacted separately with thioglycolic acid to get the desired l-(2-p-chlorophenyl-4-thiazolidinon-l-yl)aminocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 9a,b.These newly synthesised compounds are screened for their antibacterial and antifungal activities.