Functionalization of methyl 3-acetyl-5-[(methoxycarbonyl)amino]-2-methyl-1H-indole-1-carboxylate
- Authors: Velikorodov A.V.1, Ionova V.A.1, Shustova E.A.1, Stepkina N.N.1
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Affiliations:
- Astrakhan State University
- Issue: Vol 52, No 6 (2016)
- Pages: 834-837
- Section: Article
- URL: https://bakhtiniada.ru/1070-4280/article/view/214504
- DOI: https://doi.org/10.1134/S1070428016060129
- ID: 214504
Cite item
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.
About the authors
A. V. Velikorodov
Astrakhan State University
Author for correspondence.
Email: avelikorodov@mail.ru
Russian Federation, pl. Shaumyana 1, Astrakhan, 414000
V. A. Ionova
Astrakhan State University
Email: avelikorodov@mail.ru
Russian Federation, pl. Shaumyana 1, Astrakhan, 414000
E. A. Shustova
Astrakhan State University
Email: avelikorodov@mail.ru
Russian Federation, pl. Shaumyana 1, Astrakhan, 414000
N. N. Stepkina
Astrakhan State University
Email: avelikorodov@mail.ru
Russian Federation, pl. Shaumyana 1, Astrakhan, 414000
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