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Effects of acids on orientation in the reaction of 5-formyl-4-(1-pyridino)azole 2-oxides with aromatic amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Azole betaines containing vicinal formyl and pyridinium groups react with aromatic amines to give, when protonated by weak or strong acids, azolidine-2,4-dione-5-aldehyde azomethines (I) or 4-aryliminoazolidin-2-ones (II), respectively. Compound (I) is formed by the intramolecular migration of the oxygen in the 4-position of the azole, and (II) by decarbonylation of the original betaine. The orientation in the reaction of dicentric nucleophiles (hydrazines and o-phenylenediamine) is independent of the extent of protonation, giving betaine hydrazones and azolo[4,5-b]benzodiazepines, respectively. The PMR mass spectra of the products are discussed.

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Literature cited

  1. R. O. Kochkanyan, N. V. Spitsyn, and S. N. Baranov, Khim. Geterotsikl. Soedin., No. 2, 272 (1983).

    Google Scholar 

  2. R. O. Kochkanyan, S. S. Lukanyuk, T. A. Dmitruk, and N. G. Korzenevskaya, Zh. Obshch. Khim., 55, 155 (1985).

    Google Scholar 

  3. V. S. Garkusha-Bozhko, R. O. Kochkanyan, O. P. Shvaika, and S. N. Baranov, Khim. Geterotsikl. Soedin., No. 3, 372 (1976).

    Google Scholar 

  4. H, Wittman, P. Beutel, and E. Ziegler, Monatsh. Chem., 100, 1624 (1969).

    Google Scholar 

  5. H. Wittman, P. Beutel, and E. Ziegler, Monatsh, Chem., 100, 1619 (1969).

    Google Scholar 

  6. É. E. Gilbert, The Sulfonation of Organic Compounds [Russian translation], Khimiya, Moscow (1969), p, 372.

    Google Scholar 

  7. R. O. Kochkanyan, A. N. Zaritovskii, N. A. Klyuev, B. M. Zolotarev, and S. N. Baranov, Khim, Geterotsikl, Soedin., No. 2, 255 (1978).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Physical Chemistry and Carbon Chemistry, Academy of Sciences of the Ukrainian SSR, 340114, Donetsk

    R. O. Kochkanyan, A. N. Zaritovskii, A. B. Kruglova & N. A. Klyuev

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  1. R. O. Kochkanyan
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  2. A. N. Zaritovskii
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  3. A. B. Kruglova
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  4. N. A. Klyuev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 233–238, February, 1986.

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Kochkanyan, R.O., Zaritovskii, A.N., Kruglova, A.B. et al. Effects of acids on orientation in the reaction of 5-formyl-4-(1-pyridino)azole 2-oxides with aromatic amines. Chem Heterocycl Compd 22, 186–192 (1986). https://doi.org/10.1007/BF00519941

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  • DOI: https://doi.org/10.1007/BF00519941

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