Quinazolines 1. Synthesis and chemical reactions of 6-chlorosulfonyl-quinazoline-2,4-diones

  • R. Sh. Kuryazov
  • N. S. Mukhamedov
  • Kh. M. Shakhidoyatov
Article
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Abstract

Treatment of quinazoline-2,4-dione and its symmetrical 1,3-dialkyl derivatives with chlorosulfonic acid gave the corresponding 6-chlorosulfonylquinazoline-2,4-diones. Reaction of the compounds obtained with nucleophilic agents (water, ammonia, aliphatic and cyclic amines) gave the corresponding free 2,4-dioxoquinazoline-6-sulfonic acids, 6-sulfamidoquinazoline-2,4-diones, and 2,4-dioxoquinazoline-6-sulfonic acid amides.

Keywords

2,4-dioxoquinazoline-6-sulfonic acid amides 2,4-dioxoquinazoline-6-sulfonic acids symmetrical 1,3-dialkylquinazoline-2,4-diones 6-chlorosulfonylquinazoline-2,4-diones nucleophilic and electrophilic substitution 
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References

  1. 1.
    A. H. Amin, D. R. Mehta, and S. S. Samarth, Progr. Drug Res., 218 (1970).Google Scholar
  2. 2.
    S. Johne, Pharmazie, 36, 583 (1981).Google Scholar
  3. 3.
    L. N. Yakhontov, S. S. Liberman, G. P. Zhikhareva, and K. K. Kuz’mina, Khim.-Farm. Zh., 11, No. 5, 14 (1977).Google Scholar
  4. 4.
    O. N. Volzhina and L. N. Yakhontov, Khim.-Farm. Zh., 16, No. 10, 23 (1982).Google Scholar
  5. 5.
    T. Hisano, K. Shoji, and M. Ichikawa, Org. Prep. Proced. Int., 4, 271 (1975).Google Scholar
  6. 6.
    N. Tulyaganov in: Pharmacology of Natural Compounds [in Russian], Fan Publishing House, Tashkent (1978), p. 56.Google Scholar
  7. 7.
    N. Tulyaganov, Kh. Alimdzhanov, and F. N. Dzhakhangirov in: Pharmacology of Natural Compounds [in Russian], Fan Publishing House, Tashkent (1978), p. 61.Google Scholar
  8. 8.
    N. Tulyaganov in: Pharmacology of Natural Compounds [in Russian], Fan Publishing House, Tashkent (1979), p. 71.Google Scholar
  9. 9.
    D. A. Dushamov, N. S. Mukhamedov, and N. A. Aliev in: Problems in the Development Chemistry and Technology of Organic Compounds in Uzbekistan, Sci. Conf. Coll. [in Russian], Tashkent (1988), p. 12.Google Scholar
  10. 10.
    D. A. Dushamov, N. S. Mukhamedov, Kh. M. Bobokulov, and N. A. Aliev, Khim. Prirod. Soed., 83 (2001).Google Scholar
  11. 11.
    N. S. Mukhamedov, E. L. Kristallovich, V. N. Plugar’, K. Giyasov, N. A. Aliev, and N. D. Abdullaev, Khim. Geterotsikl. Soedin., 1136 (1994). [Chem. Heterocycl. Comp., 30, 982 (1994)].Google Scholar
  12. 12.
    N. S. Mukhamedov, D. A. Dushamov, N. A. Aliev, Kh. M. Bobokulov, M. G. Levkovich, and N. D. Abdullaev, Khim. Geterotsikl. Soedin., 380 (2002). [Chem. Heterocycl. Comp., 38, 344 (2002)].Google Scholar
  13. 13.
    D. A. Dushamov, N. S. Mukhamedov, N. A. Aliev, Kh. M. Bobokulov, M. G. Levkovich, and N. D. Abdullaev, Khim. Geterotsikl. Soedin., 503 (2002). [Chem. Heterocycl. Comp., 38, 438 (2002)].Google Scholar
  14. 14.
    S. Gabriel and J. Colmen, Ber., 38, 3561 (1905).Google Scholar
  15. 15.
    M. Hedayatullah, J. Heterocyclic Chem., 18, 339 (1981).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2008

Authors and Affiliations

  • R. Sh. Kuryazov
    • 1
  • N. S. Mukhamedov
    • 1
  • Kh. M. Shakhidoyatov
    • 1
  1. 1.S. Yu. Yunusov Institute of the Chemistry of Plant SubstancesAcademy of Sciences Republic of UzbekistanTashkentUzbekistan

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