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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


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.