Chemoselectivity of indole-dicarboxylates towards hydrazine hydrate: Part III - Synthesis and antimicrobial activity of novel 4-thiazolidinonylindoles

Abstract

156-159Exclusive formation of 3-carbethoxyindol-5-yloxyacetic acid hydrazides <b style="mso-bidi-font-weight: normal">3a,b from 3-carbethoxy-5- ethoxycarbonylmethoxyindoles 2a,b reveals the chemoselectivity of the C5-methyl ester function towards the nucleophilic attack of hydrazine hydrate. These mono hydrazides 3a,b on reacting with benzaldehydes furnish 1-alkyl-5- benzalhydrazinocarbonylmethoxy-3-ethoxycarbonyl-2-methylindoles 5a-h which on treatment with thioglycolic acid afford the desired 1-alkyl-3-ethoxycarbonyl-2-methyl-5-[(2-phenyl-4-thiazolidinon-3-yl)aminocarbonylmethoxy] indoles 6a-h. All the new compounds have been screened for their antibacterial and antifungal activities. </span