Chemoselective reaction of bisheterocycle dicarboxylate towards hydrazine hydrate: Synthesis and antimicrobial activity of some new trisheterocycles:5-Pyrrolylaminocarbonyl/ oxadiazolyl/mercaptooxadiazolylmethoxy-1-furfuryl-2-methylindoles

Abstract

Chemoselectivity of C₅-ester over C₃-carbethoxy ester function of the bisheterocycle dicarboxylate towards the nucleophilic attack of hydrazine hydrate has been evidenced by the exclusive formation of 1-furfuryl-3-carbethoxy-5-hydroxy-2-methylindol-5-yloxyacetic acid hydrazide which is reacted separately with acetonyl acetone, triethyl orthoformate, carbon

disulphide and boiling ethanolic potassium hydroxide to furnish respectively the 1-furfuryl-3-carbethoxy-5-(2, 5-dimethylpyrrol-1-yl)aminocarbonylmethoxy-2-methylindole, 1-furfury l-3-carbethoxy-5-(1, 3, 4-oxadiazol-2-yl)methoxy-2-methylindole and 1-furfuryl-3 carbethoxy-5-(5-mercapto-1, 3, 4-oxadiazol-2-yl)methoxy-2-methylindole. The newly synthesized compounds are screened for their antibacterial and antifungal activities.