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Recyclization of 2,2-disubstituted 4(3H)-oxo- and 4-chloro-1,2-dihydropyrimidines to 4-aminopyridine derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The intramolecular cationotropic rearrangement of salts of two-ring 2,2-disubstituted 4-chloro-1,2-dihydropyrimidines to 4-aminopyridine derivatives was observed. Recyclization to 4-aminopyridines can take place in the reaction of two-ring 2,2-disubstituted 4(3H)-oxo-1,2-dihydropyrimidines with phosphorus oxychloride without isolation of the intermediate chloro derivatives. A probable mechanism that makes it possible to assert that the observed recyclization is a variant of the intramolecular cationotropic rearrangement that is characteristic for 2,2-dialkyl-substituted 1,2-dihydropyrimidines with functional substituents (for example, oxo or chloro) in the 4 position of the ring is discussed.

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Authors and Affiliations

  1. State Scientific-Research and Planning Institute of the Nitrogen Industry and Products of Organic Synthesis, 109815, Moscow

    A. V. Upadysheva, N. D. Grigor'eva, Yu. S. Ryabokobylko & A. P. Znamenskaya

  2. All-Union Scientific-Research Institute of Chemical Reagents and Ultrapure Chemical Substances, 107258, Moscow

    A. V. Upadysheva, N. D. Grigor'eva, Yu. S. Ryabokobylko & A. P. Znamenskaya

Authors
  1. A. V. Upadysheva
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  2. N. D. Grigor'eva
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  3. Yu. S. Ryabokobylko
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  4. A. P. Znamenskaya
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 107–111, January, 1983.

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Upadysheva, A.V., Grigor'eva, N.D., Ryabokobylko, Y.S. et al. Recyclization of 2,2-disubstituted 4(3H)-oxo- and 4-chloro-1,2-dihydropyrimidines to 4-aminopyridine derivatives. Chem Heterocycl Compd 19, 95–100 (1983). https://doi.org/10.1007/BF00512825

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  • DOI: https://doi.org/10.1007/BF00512825

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