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Russian Journal of Organic Chemistry

, Volume 52, Issue 6, pp 834–837 | Cite as

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

  • A. V. Velikorodov
  • V. A. Ionova
  • E. A. Shustova
  • N. N. Stepkina
Article
  • 36 Downloads

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.

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Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • A. V. Velikorodov
    • 1
  • V. A. Ionova
    • 1
  • E. A. Shustova
    • 1
  • N. N. Stepkina
    • 1
  1. 1.Astrakhan State UniversityAstrakhanRussia

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