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Communication | Regular issue | Vol 12, No. 1, 1979, pp.45-49
Published online, 1st January, 1970
DOI: 10.3987/R-1979-01-0045
An Unusual Synthetic Route to Mesoionic Pyrimidines

Frank Mercer, Louis Hernandez, Jr., and Harold W. Moore*

*Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616-5295, U.S.A.

Abstract

A new and novel synthetic route to the rare mesoionic pyrimidines is described. This involves the cycloaddition of formimidates to 1,4-dipolar zwitterions. The zwitterions themselves are generated from three independent pathways, i.e., 1) the thermolysis of 4-azido-2-pyrrolinones, 2) the thermolysis of 3-cyano-2-azetidinones, and 3) from the cycloaddition of chlorocyanoketene to formimidates.