Ambidentate reactivity of 3-azapyrylium systems in nucleophilic attack reactions

Authors

  • C. B. Бородаев Scientific Research Institute of Physical and Organic Chemistry, Rostov State University, Rostov-on-Don 344090
  • M. E. Kлецкий Scientific Research Institute of Physical and Organic Chemistry, Rostov State University, Rostov-on-Don 344090
  • H. B. Шибаeва Scientific Research Institute of Physical and Organic Chemistry, Rostov State University, Rostov-on-Don 344090

Abstract

It has been shown that recyclization of 4-acylmethyl-3-azapyrylium salts under the influence of primary amines affords 4-(β-hydroxystyryl)pyrimidinium salts, which, upon further heating with the amine, are recyclized to form 4-acylaminopyridinium salts. It has been established that nucleophilic attack of 6-acylmethyl-substituted 3-azapyrylium salts in aqueous NaOH solution leads to functionally substituted pyridines. By means of MNDO quantum-chemical calculations with an accounting for solvation effects, in a continuum model, it has been shown that two directions of nucleophilic attack of the azapyrylium ring — at positions 2 and 6 — are equally probable.

How to Cite
Borodaev, S.V., Kletskii, M.E. & Shibaeva, N.V. Chem. Heterocycl. Compd. 1994, 30, 612. [Khim. Geterotsikl. Soedin. 1994, 697.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169845

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Published

1994-05-25

Issue

No. 5 (1994)

Section

Original Papers