Intramolecular 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from Ethoxycarbonylcarbenoids and Schiff Bases |
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Authors: | A. F. Khlebnikov M. S. Novikov R. R. Kostikov J. Kopf |
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Affiliation: | (1) St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia;(2) Institut fur anorganische Chemie, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany |
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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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