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4228091 
Journal Article 
CHEMOSELECTIVITY OF INDOLE DICARBOXYLATE TOWARDS HYDRAZINE HYDRATE - SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF OXADIAZOLYL PYRROLYL TRIAZOLYL PYRAZOLYLMETHOXYINDOLE DERIVATIVES 
Gadaginamath, GS; Joshi, RG; Kamat, AG 
1995 
1 
Revue Roumaine de Chimie
ISSN: 0035-3930 
40 
5 
475-484 
English 
WOS:A1995TC55000010 
The exclusive formation of substituted indol-5-yloxyacid hydrazides (4a-h) from 3-carbethoxy-5-ethoxy-carbonylmethoxyindoles (2a-h) revealed the chemoselectivity of C-5 ester over C-3 carboxy ester function towards the nucleophilic attack of hydrazine hydrate. These hydrazides (4a-h) were treated separately with triethyl-orthoformate, carbon disulphide and ethanolic potassium hydroxide followed by treatment with hydrazine hydrate (99%), acetonyl, acetone and acetyl acetone to furnish the desired substituted 5-(1',3',4'-oxadiazol-2'-yl)-methoxyindoles (5a-h), 5-(4'-amino-5'-mercapto-1'-2', 3'-triazol-3'-yl) methoxyindoles (6a-h), 5-(2', 5'-dimethyl-pyrrol-1'-yl) aminocarbonylmethoxyindoles (7a-h) and 5-(3', 5'-dimethylpyrazol-1'-yl) carbonylmethoxyindoles (8a-h), respectively: The Schiff base of hydrazide (9d) obtained from hydrazide (4d) and ethyl acetoacetate on heating with o-dichlorobenzene furnished dimer (11d) instead of pyrazolonylindole (10d). The newly synthesised compounds were screened for their antibacterial and antifungal activities. 
Chemistry