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

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

Chemoselective reaction of benz[<i>g</i>]indole dicarboxylate towards hydrazine hydrate: Bisheterocycles: Synthesis and antimicrobial activity of some new 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-oxadiazolyl/triazolyl/ pyrrolylaminocarbonylmethoxy-2-methylbenz[<i>g</i>]indoles

794-800The exclusive formation of 1-[2-hydroxyethyl]-3-ethoxycarbonyl-2-methyl benz[g] indol-5-yloxyacetic acid hydrazide 6 from 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-methoxycarbonylmethoxy-2-methylbenz[g]indole 3 revealed the chemo­selectivity of the C5-ester over C3-ester towards nucleophilic attack of hydrazine hydrate. This monocarbohydrazide 6 is reacted separately with CS2/KOH, acetonyl acetone and isothiocyanates to secure the desired 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-(5-mercapto-1,3,4,-oxadiazl-2-y1)methoxy-2-methylbenz[g]indole 7, 1-[2-hydroxyethyl]-3-ethoxy-carbonyl-5-(2,5-dimethylpyrrol-1-yl)aminocarbonylmethoxy-2-methylbenz[g]indole 8 and 1-[2-hydroxyethyl]-3-ethoxy­carbonyl-5-(N-substituted thiosemicarbazinocarbonyl)methoxy-2-methylbenz[g]indole 9a-c. These thiosemicarbazides 9a-c are reacted with 4% NaOH to produce the 1-[2-hydroxyethyl]2-methybenz[g]indol-5-(4-substituted-5-mercapto-1,2,4-triazol-3-yl)methoxy-3-caboxylic acids 10a-c. All theses newly synthsised compounds are screened for their antimicrobial activities

1,3-Dipolar cycloaddition reactions: Synthesis and antimicrobial activity of novel 1-triazolylethylindole and 1-triazolylethylbenz[g]indole derivatives

1068-1073Indole azide 4 and benz[g]indole azide 12 are reacted separately with dimethyl acetylenedicarboxylate to secure the desired 1-[4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 5 and 1-[4,5-di­methoxy­carbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylbenz[g]indole 13, respectively. The reac­tion of indole azide 4 and benz[g]indole azide 12 with ethyl propiolate has been found to be regiospecific and produce only the 1-[4-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 6 and 1-[4-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylbenz[g]indole 14, respectively. Indole azide 4 is also reacted with ethyl phenylpropolate to secure two isomeric products 1-[4-ethoxycarbonyl-5-phenyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 8 and 1-[4-phenyl-5-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole 9. All these newly synthesised compounds are screened for their antimicrobial activities