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/pyrrolyl­aminocarbonylmethylindoles

Abstract

1663-1668Chemoselectivity of 1-ester over C3-ester of the indole dicarboxylates 3a,b towards the nucleophilic attack of hydrazine hydrate has been evidenced by the exclusive formation of 1-hydrazinocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 5a,b which have been further reacted separately with CS2/KOH, p-chlorobenzaldehyde and acetonyl acetone to furnish the 1-(5-mercapto-1,3,4-oxadiazol-2-yl)methyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 6a,b, 1-p-Chlorobenzyl­idene­hydrazinocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 7a,b and 1-(2,5-dimethyl­pyrrol-1-yl)­amino­carbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 8a,b respectively. The Schiff’s bases 7a,b are reacted separately with thioglycolic acid to get the desired 1-(2-p-chlorophenyl-4-thiazolidinon-1-yl)aminocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 9a,b. These newly synthesised compounds are screened for their antibacterial and antifungal activities