Russian Journal of Organic Chemistry

, Volume 46, Issue 7, pp 971–975 | Cite as

Some condensations of methyl 4-acetylphenylcarbamate

  • A. V. Velikorodov
  • N. M. Imasheva
  • A. K. Kuanchalieva
  • O. Yu. Poddubnyi
Article

Abstract

Condensation of methyl 4-acetylphenylcarbamate with isatin in the presence of diethylamine afforded methyl 4-[(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetyl]phenylcarbamate which was converted into the corresponding chalcone on heating in glacial acetic acid in the presence of hydrochloric acid. 1,3-Dipolar cycloaddition to that chalcone of azomethine ylide generated from 2-phenacylisoquinolinium bromide by the action of triethylamine gave methyl 4-(3′-benzoyl-2-oxo-1′,2,2′,3,3′,10b′-hexahydro-1H-spiro-[indole-3,1′-pyrrolo[1,2-a]isoquinolin]-2′-ylcarbonyl)phenylcarbamate. Condensation of 2-hydroxy- and 2,4-dihydroxybenzaldehydes with methyl 4-acetylphenylcarbamate in the presence of gaseous hydrogen chloride resulted in the formation of chromenium salts with a methoxycarbonylaminophenyl fragment on the C2 atom in the heteroring.

Keywords

Glacial Acetic Acid Chalcone Isatin Light Yellow Crystal Mesomeric Effect 

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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • A. V. Velikorodov
    • 1
  • N. M. Imasheva
    • 1
  • A. K. Kuanchalieva
    • 1
  • O. Yu. Poddubnyi
    • 1
  1. 1.Astrakhan State UniversityAstrakhanRussia

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