Abstract
5-Cyano-6-(β-dimethylamino)vinyl-1-methyl-4-pyrimidinone was synthesized by the interaction of α-cyano-β-(N-methylamino)crotonamide with N,N-dimethylformamide diethylacetal. Recyclization of the product in alkaline medium leads to 3-cyano-4-methylamino-2-pyridone. Nitration of the latter and transformation of the nitropyridone by boiling in POCl3 gave 2-chloro-3-cyano-4-methylamino-5-nitropyridine. This is a key compound for various transformations including the synthesis of derivatives of dipyrido[1,2-a:3,2-e]pyrimidine, thieno[2,3-b]pyridine, and (2-pyridylamino)polyene derivatives.
Similar content being viewed by others
References
V. G. Granik, E. O. Sochneva, and N. P. Solov'eva, Khim. Geterotsikl. Soedin., 416 (1980).
V. G. Granik, A. M. Zhidkova, and R. A. Dubinskii, Khim. Geterotsikl. Soedin., 269 (1981).
V. G. Granik, A. M. Zhidkova, and R. A. Dubinskii, Khim. Geterotsikl. Soedin., 518 (1982).
M. Yu. Yakovlev, A. V. Kadushkin, N. P. Solov'eva, O. S. Anisimova, and V. G. Granik, Tetrahedron, 54, 5775 (1998).
L. V. Ershov, S. S. Kiselev, and V. G. Granik, Khim. Geterotsikl. Soedin., 538 (1984).
S. A. Ryndina, A. V. Kadushkin, N. P. Solov'eva, and V. G. Granik, Khim. Geterotsikl. Soedin., 1643 (2000).
V. G. Granik, A. V. Kadushkin, and U. Liebscher, Adv. Heterocycl. Chem., 72, 79 (1998).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Krichevsky, E.S., Alekseeva, L.M. & Granik, V.G. Synthesis and Chemical Conversions of 2-Chloro-3-cyano-4-methylamino-5-nitropyridine. Chemistry of Heterocyclic Compounds 39, 328–334 (2003). https://doi.org/10.1023/A:1023962726390
Issue Date:
DOI: https://doi.org/10.1023/A:1023962726390