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


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.


Copper Nitrogen Atom Pyrrole Schiff Dicarboxylic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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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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