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Communication | Regular issue | Vol 24, No. 11, 1986, pp.3053-3058
Published online, 1st January, 1970
DOI: 10.3987/R-1986-11-3053
Cyclization of Dinitriles by Hydrogen Halides. 3. The influence of the Tautomerism

Pedro Victory* and Miquel Garriga

*Departmento de Química Orgánica, Instituto Químico de Sarriá, Universitat de Barcelona, 08028 Barcelona, Spain


In order to study the possible influence of the tautomerism in the direction of cyclization by hydrogen halides of the 6-cyanamino-5-cyano-3,4-dihydro-2-pyridones (3), the non-tautomeric N-methylcyanamino substituted derivatives 10 have been synthesized. The reaction of 10 with hydrogen halides leads regiospecifically to the 4-halogeno-2-imino-1-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones 12, 13 and 14, showing the insufficient reactivity of the N-cyano group in front of the conjugated one. On the basis of the results of the cyclization of 10, an interpretation of the more complex cyclization of 3 is proposed.