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Oxidative cyclocondensation of cyclic thio(seleno)ureas. 4. Electronic effects of the substituents and the medium

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have studied the electronic effect of substituents, steric factors, the medium, and the nature of the oxidizing agent on oxidative cyclocondensation of 2-thioxo-4-quinazolone and its substituted derivatives. We have found that electron-donor substituents promote the reaction while electronacceptor substituents inhibit the reaction.

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References

  1. N. I. Mukarramov and B. A. Urakov, Khim. Prirod. Soedin., Special Issue, 109 (1999).

  2. R. C. Elderfield, ed., Heterocyclic Compounds [Russian translation], Mir, Moscow (1965), Vol. 7, p. 427.

    Google Scholar 

  3. J. Goerdeler and M. Willig, Chem. Ber., 88, 1071 (1955).

    CAS  Google Scholar 

  4. J. Goerdeler and A. Fincke, Chem. Ber., 89, 1033 (1956).

    CAS  Google Scholar 

  5. S. Lotz and G. Gattow, Z. Anorg. Allg. Chem., 581, 99 (1990).

    Article  CAS  Google Scholar 

  6. G. Barnikov and J. Bodeker, Chem. Ber., 100, 1394 (1967).

    Google Scholar 

  7. C. P. Joshua and N. P. Kesavan, Indian J. Chem., 12, 962 (1974).

    CAS  Google Scholar 

  8. C. P. Joshua and N. P. Kesavan, Indian J. Chem., 13, 241 (1975).

    CAS  Google Scholar 

  9. C. P. Joshua and K. N. Rajasekharan, Aust. J. Chem., 30, 1819 (1977).

    Article  CAS  Google Scholar 

  10. D. Griffiths, R. Hull, and T. P. Seden, J. Chem. Soc., Perkin Trans. 1, 2608 (1980).

  11. D. J. Greig, D. G. Hamilton, M. McPherson, R. M. Paton, and J. Crosby, J. Chem. Soc., Perkin Trans. 1, 607 (1987).

  12. J. Goerdeler, Chem. Ber., 87, 57 (1954).

    CAS  Google Scholar 

  13. P. Kruger, Ber., 18, 1053 (1885).

    Google Scholar 

  14. B. F. Kurzer, J. Chem. Soc., 1 (1955).

  15. J. Goerdeler and F. Bechlars, Chem. Ber., 88, 843 (1955).

    CAS  Google Scholar 

  16. N. S. Cho and H. I. Shon, J. Heterocycl. Chem., 28, 1645 (1991).

    Article  CAS  Google Scholar 

  17. A. R. Katritzky, Adv. Heterocycl. Chem., 3, 263 (1965).

    Google Scholar 

  18. G. L’Abbe, E. V. Lock, R. Albert, S. Toppet, G. Verhelst, and G. Smets, J. Am. Chem. Soc., 96, 3973 (1974).

    Article  Google Scholar 

  19. R. Neidlein and K. Salzmann, Synthesis, 52 (1975).

  20. G. L’Abbe, G. Verhelst, Ch.-Ch. Ju, and S. Toppet, J. Org. Chem., 40, 1728 (1975).

    Article  CAS  Google Scholar 

  21. G. L’Abbe and Ch. Yu, Chem. Ind. (London), No. 8, 312 (1977).

  22. J. Goerdeler, D. Gross, and R. Keinke, Chem. Ber., 96, 1289 (1963).

    CAS  Google Scholar 

  23. V. I. Cohen, Synthesis, 768 (1978).

  24. Kh. M. Shakhidoyatov, B. A. Urakov, N. I. Mukarramov, M. A. Ashirmatov, and V. P. Bruskov, Khim. Geterotsikl. Soedin., 845 (1996).

  25. D. Barton and W. D. Ollis (editors), Comprehensive Organic Chemistry [Russian translation], Khimiya, Moscow (1983), Vol. 5, p. 253.

    Google Scholar 

  26. Organicum: Practical Handbook of Organic Chemistry [Russian translation from German Organikum], Mir, Moscow (1979), Vol. 2, p. 353.

  27. S. J. Niementowski, J. Prakt. Chem., 51, 564 (1895).

    Article  CAS  Google Scholar 

  28. S. Yangibaev, Dissertation in competition for the academic degree of Candidate of Chemical Sciences, Tashkent (1985).

  29. B. A. Urakov, Dissertation in competition for the academic degree of Candidate of Chemical Sciences, Alma-Ata (1990).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 616–622, April, 2006.

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Mukarramov, N.I., Urakov, B.A. & Shakhidoyatov, K.M. Oxidative cyclocondensation of cyclic thio(seleno)ureas. 4. Electronic effects of the substituents and the medium. Chem Heterocycl Compd 42, 540–545 (2006). https://doi.org/10.1007/s10593-006-0123-1

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  • DOI: https://doi.org/10.1007/s10593-006-0123-1

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