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Synthesis of 2-Substituted and 2,3-Disubstituted Quinazolin-4-ones Containing a Sterically Hindered Phenol Residue

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A series of 2-substituted and 2,3-disubstituted quinazolin-4-ones containing a 3,5-di(tert-butyl)-4-hydroxyphenyl group has been synthesized. They were prepared by the condensation of carboxylic acid imino ester hydrochlorides containing the indicated fragment with ethyl anthranilate and also by the reaction of azomethines, N-acylhydrazones, or the 4-phenylthiosemicarbazone of 3,5-di(tert-butyl)-4-hydroxybenzaldehyde with 2-methyl-4H-2,1-benzoxazin-4-one.

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REFERENCES

  1. V. I. Kelarev, F. Laauad Yakh'ya, R. A. Karakhanov, A. F. Lunin, and O. V. Malova, Khim. Geterotsikl. Soedin., 107 (1986).

  2. V. I. Kelarev, V. N. Koshelev, R. A. Karakhanov, V. G. Kartsev, S. Yu. Zasedatelev, A. M. Kuatbekov, and G. V. Morozova, Khim. Geterotsikl. Soedin., 514 (1995).

  3. V. I. Kelarev, V. N. Koshelev, N. V. Belov, O. V. Malova, and R. A. Karakhanov, Khim. Geterotsikl. Soedin., 240 (1994).

  4. V. I. Kelarev, V. N. Koshelev, N. V. Belov, O. V. Malova, and R. A. Karakhanov, Khim. Geterotsikl. Soedin., 224 (1995).

  5. V. I. Kelarev, V. N. Koshelev, and M. A. Silin, Khim. Geterotsikl. Soedin., 822 (1997).

  6. M. A. Silin, V. I. Kelarev, and V. Abu-Ammar, Khim. Geterotsikl. Soedin., 256 (2000).

  7. Kh. M. Shakhidoyatov, 4-Quinazolones and their Biological Activity [in Russian], Fan, Tashkent (1988).

  8. V. I. Kelarev and V. N. Koshelev, Usp. Khim., 64, 339 (1995).

    Google Scholar 

  9. V. I. Kelarev, S. G. Shvekhgeimer, V. N. Koshelev, G. A. Shvekhgeimer, and A. F. Lunin, Khim. Geterotsikl. Soedin., 889 (1984).

  10. J. P. Pauchard and A. E Siegrist, Helv. Chim. Acta, 61, 129 (1978)

    Google Scholar 

  11. A. K. Mukerjee and P. Kumar, Chem. and Ind., 936 (1980).

  12. K. D. Deodkar, S. D. Samant, S. R. Pednekar, D. S. Kanekar, A. A. Inamdar, and P. Y. Patkar, Indian J. Chem., 21B, 67 (1982).

    Google Scholar 

  13. D. J. Brown, in: A. R. Katritzky (editor), Comprehensive Heterocyclic Chemistry, Pergamon Press, Vol. 3, Oxford (1984), p. 57.

  14. A. R. Katritzky (editor), Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya, Moscow, Leningrad (1966), p. 569.

  15. R. M. Silverberg, G. C. Bassler, and T. C. Morrill, Spectroscopic Identification of Organic Compounds [Russian translation], Mir, Moscow (1977).

  16. V. V. Ershov, G. A. Nikiforov, and A. A. Volod'kin, Sterically Hindered Phenols [in Russian], Khimiya, Moscow (1972).

  17. T. N. Pliev, Dokl. Akad. Nauk, SSSR, 176, 113 (1967).

    Google Scholar 

  18. T. N. Pliev, Zh. Prikl. Spektrosk., 13, 124 (1970).

    Google Scholar 

  19. F. Yu. Rachinskii, G. D. Bol'shakov, Yu. A. Bruk, M. Z. Kremen, L. V. Pavlova, T. G. Potapenko, and N. M. Slachevskaya, in: The Chemistry of Sulfo Organic Compounds Contained in Oils and Oil Products, Khimiya, Vol. 7, Moscow (1964), p. 45.

    Google Scholar 

  20. Yu. A. Bruk, F. Yu. Rachinskii, L. V. Zolotova, M. Z. Borodulina, Zh. Obshch. Khim., 42, 1603 (1972).

    Google Scholar 

  21. I. A. Golubeva, E. V. Klinaeva, V. N. Koshelev, V. I. Kelarev, and I. A. Gol'dsher, Khim. Tekhnol. Topliv Masel., No. 1, 30 (1997).

  22. V. I. Kelarev, M. A. Silin, I. G. Kotova, K. N. Kobrakov, I. A. Rybina, and V. K. Korolev, Khim. Geterotsikl. Soedin., 243 (2003).

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Authors and Affiliations

  1. I. M. Gubkin Russian State Oil and Gas University, Moscow, 117917; himeko@dol.ru

    V. I. Kelarev, M. A. Silin, V. N. Koshelev & O. A. Borisova

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  1. V. I. Kelarev
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  2. M. A. Silin
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  3. V. N. Koshelev
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  4. O. A. Borisova
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Kelarev, V.I., Silin, M.A., Koshelev, V.N. et al. Synthesis of 2-Substituted and 2,3-Disubstituted Quinazolin-4-ones Containing a Sterically Hindered Phenol Residue. Chemistry of Heterocyclic Compounds 40, 616–621 (2004). https://doi.org/10.1023/B:COHC.0000037317.38046.fc

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  • DOI: https://doi.org/10.1023/B:COHC.0000037317.38046.fc

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