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


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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.

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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