Synthesis and antimicrobial activity of 6-bromo-1-butyl-3-ethoxycarbonyl-2-(4-chloro-phenoxy) methyl-5-(4-phenyl-5-mercapto-1,2,4-triazol-3-yl) methoxyindole

Citation
Gs. Gadaginamath et Sa. Patil, Synthesis and antimicrobial activity of 6-bromo-1-butyl-3-ethoxycarbonyl-2-(4-chloro-phenoxy) methyl-5-(4-phenyl-5-mercapto-1,2,4-triazol-3-yl) methoxyindole, I J HET CHE, 9(1), 1999, pp. 39-42
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
09711627 → ACNP
Volume
9
Issue
1
Year of publication
1999
Pages
39 - 42
Database
ISI
SICI code
0971-1627(199907/09)9:1<39:SAAAO6>2.0.ZU;2-H
Abstract
6-Bromo-1-butyl-3-ethoxycarbonyl-5-ethoxycarbonylmethoxy-2-methylindole (2) was brominated regioselectively with NBS in presence of benzoylperoxide in CCl4 to secure 2-bromomethylindole derivative (3), which was then reacted with 4-chlorophenol to get corresponding 2-(4-chlorophenoxy) methylindole d erivative (4). Hydroysis of compound (4) by ethanolic NaOH gave the diacid (5). Indole diester (4) was reacted with hydrazine hydrate to give exclusiv ely 3-ethoxycarbonylindoie-5-yloxyacetic acid hydrazide (6) which was treat ed with phenylisothiocyanate followed by NaOH (4%) solution to obtain the d esired 6-bromo-1-butyl-2-(4-chlorophenoxy) methyl-3-ethoxy carbonyl-5-(4-ph enyl-5-mercapto-1,2,4-triazol-3-yl) methoxyindole (9). All the newly synthe sized compounds were screened for their antimicrobial activities.