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IJC-B Vol.44B(04) [April 2005] >


Title: Chemoselective reaction of benz[g]indole dicarboxylate towards hydrazine hydrate: Bisheterocycles: Synthesis and antimicrobial activity of some new 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-oxadiazolyl/triazolyl/ pyrrolylaminocarbonylmethoxy-2-methylbenz[g]indoles
Authors: Bhovi, Manjunath G
Gadaginamath, Guru S
Issue Date: Apr-2005
Publisher: CSIR
IPC CodeInt.Cl.7 C 07 D 209/04
Abstract: The 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 chemo¬≠selectivity 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-ethoxy¬≠carbonyl-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.
Page(s): 794-800
ISSN: 0975-0983(Online); 0376-4699(Print)
Source:IJC-B Vol.44B(04) [April 2005]

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