TY - JOUR

T1 - Intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated from ethoxycarbonylcarbenoids and Schiff bases

AU - Khlebnikov, A. F.

AU - Novikov, M. S.

AU - Kostikov, R. R.

AU - Kopf, J.

N1 - Funding Information: This study was performed under financial support by the Program “Universities of Russia” (project no. ur.05.01.316) and by the Russian Foundation for Basic Research (project no. 05-03-33257).

PY - 2005/9

Y1 - 2005/9

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=28444488951&partnerID=8YFLogxK

U2 - 10.1007/s11178-005-0344-2

DO - 10.1007/s11178-005-0344-2

M3 - Article

AN - SCOPUS:28444488951

VL - 41

SP - 1341

EP - 1348

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 9

ER -