SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW 6-BROMO-1-BUTYL-3-ETHOXYCARBONYL-2-(N-METHYL-N-PHENYLAMINO)METHYL-5-(1,2,3,4-TETRAZOL-5-YL)METHOXYINDOLE

摘要

6-bromo-1-butyl-3-ethoxycarbonyl-2-methylindol-5-yIoxyacetonitrile (2) was prepared by reacting 5-hydroxy-indole with chloroacetonitrile in refluxing acetone with K_2CO_3 and catalytic amount of KI. Compound 2 was then subjected to regioselective bromination with NBS in presence of dibenzoyl peroxide in CCl_4 to yield exclusively 6-bromo-2-bromomethyl-1-butyl-3-ethoxycarbonylindol-5-yIoxyacetonitrile (3) which was condensed with N-methyl-N-phenylamine to obtain 2-(N-methyl-N-phenylamino)methylindol-5-yloxyacetonitrile (4). The 5-(1,2,3,4-tetrazol-5-yl)methoxyindole (5) was prepared by heating compound 4 at reflux with sodium azide, lithium chloride and ammonium chloride in DMF. All the newly prepared compounds were screened for their antimicrobial activities.