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Paper | Regular issue | Vol 24, No. 12, 1986, pp.3473-3476
Published online, 1st January, 1970
DOI: 10.3987/R-1986-12-3473
Pyrimidinium N-Dicyanomethylide. Synthesis and Reactivity towards Dimethyl Acetylenedicarboxylate

Antonio de la Hoz,* José Luis G. de Paz, Enrique Díez-Barra, José Elguero, and Carmen Pardo

*Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madridas, Ciudad Universitaria, E-28040 Madrid, Spain

Abstract

The titled compound (1a) has been prepared by reaction of pyrimidine with tetracyanoethyleneoxide (TCNEO). Reaction of 1a with DMAD yielded two regioisomer pyrrolopyrimidines (2a and 3a), via a 1,3-dipolar cycloaddition. Concerning the regioselectivity of the reaction, experimental results are in agreement with theoretical calculations.