Russian Journal of Organic Chemistry

, Volume 41, Issue 9, pp 1341–1348 | Cite as

Intramolecular 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from Ethoxycarbonylcarbenoids and Schiff Bases

  • A. F. Khlebnikov
  • M. S. Novikov
  • R. R. Kostikov
  • J. Kopf
Article

Abstract

Decomposition of ethyl diazoacetate in the presence of copper, copper acetylacetonate, or copper trifluoroacetylacetonate and ethyl 4-[2-(R-imino)phenoxymethyl]-2-butenoate leads to formation of chromeno-[4,3-b]pyrrole-2,3-dicarboxylic acid derivatives. The reactions involve intermediate formation of azomethine ylides which undergo regio- and stereoselective intramolecular cycloaddition at the C=C bond to afford chromeno[4,3-b]pyrroles. The steric structure of the product depends on the configuration of intermediate ylide and nature of the substituent at the ylide nitrogen atom.

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Copyright information

© MAIK "Nauka/Interperiodica" 2005

Authors and Affiliations

  • A. F. Khlebnikov
    • 1
  • M. S. Novikov
    • 1
  • R. R. Kostikov
    • 1
  • J. Kopf
    • 2
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut fur anorganische ChemieHamburgGermany

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