Functionalization of methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate

doi:10.1134/S1070428016060129

Paper

Functionalization of methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate

Published Jul 24, 2016 · A. V. Velikorodov, V. A. Ionova, E. A. Shustova

Russian Journal of Organic Chemistry

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Abstract

Oxidative heterocyclization of methyl 3-{1-[2-(carbamoylhydrazinylidene)]ethyl}-2-methyl-5-[(methoxycarbonyl)amino]-1H-indole-1-carboxylate by the action of selenium dioxide in acetic acid and heating of the corresponding thiosemicarbazone in boiling acetic anhydride gave 1,2,3-selenadiazole and 2,3-dihydro-1,3,4-thiadiazole derivatives, respectively. Methyl 3-acetyl-2-methyl-5-[(methoxycarbonyl)amino]-1H-indole-1-carboxylate reacted with selenium dioxide in dioxane–water (30: 1) at 80‒90°C to form methyl 5-[(methoxycarbonyl)amino]-2-methyl-3-(2-oxoacetyl)-1H-indole-1-carboxylate whose condensation with o-phenylenediamine afforded methyl 2-methyl-5-[(methoxycarbonyl)amino]-3-(quinoxalin-2-yl)-1H-indole-1-carboxylate.

Study Snapshot

This study demonstrates the potential of methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate for functionalization with selenium dioxide, resulting in 1,2,3-selenadiazole and 2,3

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Functionalization of methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate

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