SYNTHESIS AND CHEMICAL CONVERSIONS OF 2-CHLORO-3-CYANO-4-METHYLAMINO-5-NITROPYRIDINE

Authors

  • Э. С. Кричевский NIOPIK State Scientific Center of the Russian Federation, Moscow 103787
  • Л. М. Алексеева NIOPIK State Scientific Center of the Russian Federation, Moscow 103787
  • В. Г. Граник NIOPIK State Scientific Center of the Russian Federation, Moscow 103787

Keywords:

nitropyridine, 2-pyridone, 4-pyrimidinone, Torp–Ziegler reaction

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.

How to Cite
Krichevsky, E. S.; Alekseeva, L. M.; Granik, V. G. Chem. Heterocycl. Compd. 2003, 39, 328. [Khim. Geterotsikl. Soedin. 2003, 371.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1023962726390

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Published

2003-03-25

Issue

No. 3 (2003)

Section

Original Papers