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Synthesis and structure of 2-hydroxy-3-formylbenzo[b]thiophene azomethines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A number of 2-hydroxy-3-formylbenzo[b]thiophene azomethines and their derivatives, which model the individual tautomeric forms, were synthesized. As a result of a study of the electronic, vibrational, and PMR spectra, a ketone-amine structure, the stability of which is confirmed by quantum-mechanical calculations of the atomization energies of the individual tautomeric forms calculated by the Pariser-Parr-Pople (PPP) method within the Dewar σ, π parametrization, was assigned to these azomethines.

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Literature cited

  1. V. A. Bren', V. I. Usacheva, Zh. V. Bren', B. Ya. Simkin, and V. I. Minkin, Khim. Geterotsikl. Soedin., 631 (1974).

  2. V. A. Bren', V. I. Usacheva, and V. I. Minkin, Khim. Geterotsikl. Soedin., 920 (1972).

  3. V. A. Bren', Zh. V. Bren', and V. I. Minkin, Khim. Geterotsikl. Soedin., 154 (1972).

  4. V. S. Bogdanov, M. A. Kalik, G. M. Zhidomirov, N. D. Chuvylkin, and Ya. L. Gol'dfarb, Zh. Organ. Khim., 7, 1953 (1971).

    Google Scholar 

  5. N. M. D. Brown and D. C. Norhebel, Tetrahedron, 24, 5655 (1968).

    Google Scholar 

  6. L. E. Nivorozhkin, M. S. Korobov, B. Ya. Simkin, and V. I. Minkin, Zh. Organ. Khim., 8, 1677 (1972).

    Google Scholar 

  7. G. O. Dudek and G. P. Volpp, J. Amer. Chem. Soc., 85, 2697 (1963).

    Google Scholar 

  8. D. H. Gerlach and R. H. Holm, J. Amer. Chem. Soc., 91, 3457 (1969).

    Google Scholar 

  9. M. Dewar, Molecular Orbital Theory in Organic Chemistry [Russian translation], Moscow (1972).

  10. A. L. H. Chung and M. J. S. Dewar, J. Chem. Phys., 42, 756 (1965).

    Google Scholar 

  11. M. J. S. Dewar and A. J. Harget, Proc. Roy. Soc., (London), A, 315, 443, 457 (1970).

    Google Scholar 

  12. R. H. Glavart and F. G. Mann, J. Chem. Soc., 2127 (1952).

  13. R. P. Dickinson and B. Iddon, J. Chem. Soc., C, 1926 (1970).

  14. P. Zochon, Bull. Soc. Chim. France, 393 (1965).

  15. H. I. Bacher and W. Z. Wanmacher, Rec. Trav. Chim., 68, 247 (1949).

    Google Scholar 

  16. Matsuki Vasuo and Adachi Voshio, Chem. Abstr., 69, 67,165 (1968).

    Google Scholar 

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Communication XVIII from the series “Benzoid—Quinoid Tautomerism of Azomethines and Their Structural Analogs.” See [1] for communication XVII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 635–642, May, 1975.

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Bren', V.A., Usacheva, V.I., Minkin, V.I. et al. Synthesis and structure of 2-hydroxy-3-formylbenzo[b]thiophene azomethines. Chem Heterocycl Compd 11, 555–560 (1975). https://doi.org/10.1007/BF00480477

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  • DOI: https://doi.org/10.1007/BF00480477

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