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Benzazoles. 4. Synthesis and chemical reactions of 6-chlorosulfonylbenzoxazolin-2-ones

  • M. E. Karimova
  • D. A. Dushamov
  • R. Sh. Kuryazov
  • N. S. MukhamedovEmail author
Article
  • 152 Downloads

The corresponding 6-chlorosulfonyl derivatives were synthesized from benzoxazolin-2-one and its 3-methyl derivative by treatment with chlorosulfonic acid. By treatment of the compounds obtained with water and other nucleophilic reagents (aliphatic and heterocyclic amines) 2-oxobenzoxazoline-6-sulfonic acids and a series of their amides were obtained, while reduction with SnCl2·2H2O gave 6-mercaptobenzoxazolin-2-ones.

Keywords

amides of 2-oxobenzoxazoline-6-sulfonic acids 6-mercaptobenzoxazolin-2-ones 6-chloro-sulfonylbenzoxazolin-2-ones reduction nucleophilic substitution electrophilic substitution 

References

  1. 1.
    K. B. Abdireimov, N. S. Mukhamedov, M. Zh. Aiymbetov, and Kh. M. Shakhidoyatov, Khim. Geterotsikl. Soed., 1165 (2010). [ Chem. Heterocycl. Comp., 46, 941 (2010)].CrossRefGoogle Scholar
  2. 2.
    E. Honkanen and A. I. Virtanen, Acta Chem. Scand., 15, 221 (1961).CrossRefGoogle Scholar
  3. 3.
    J. B. Bredenberg, E. Honkanen, and A. I. Virtanen, Acta Chem. Scand., 16, 135 (1962).CrossRefGoogle Scholar
  4. 4.
    E. E. Smissman, J. B. Lapidus, and S. D. Beck, J. Am. Chem. Soc., 79, 4697 (1957).CrossRefGoogle Scholar
  5. 5.
    C. S. Tang, S. H. Chang, D. Hoo, and K. H. Yanagihara, Phytochemistry, 14, 2077 (1975).CrossRefGoogle Scholar
  6. 6.
    Ch.-M. Chen and M.-T. Chen, Phytochemistry, 15, 1997 (1976).CrossRefGoogle Scholar
  7. 7.
    N. S. Mukhamedov, E. L. Kristallovich, V. N. Plugar', K. Giyasov, N. A. Aliev, and N. D. Abdullaev, Khim. Geterotsikl. Soed., 1136 (1994). [Chem. Heterocycl. Comp., 30, 982 (1994)].CrossRefGoogle Scholar
  8. 8.
    D. A. Dushamov, N. S. Mukhamedov, Kh. M. Bobokulov, and N. A. Aliev, Khimiya Prirod. Soed., 83 (2001).Google Scholar
  9. 9.
    N. S. Mukhamedov, D. A. Dushamov, N. A. Aliev, Kh. M. Bobokulov, M. G. Levkovich, and N. D. Abdullaev, Khim. Geterotsikl. Soed., 380 (2002). [Chem. Heterocycl. Comp., 38, 344 (2002)].CrossRefGoogle Scholar
  10. 10.
    D. A Dushamov, N. S. Mukhamedov, N. A. Aliev, Kh. M. Bobokulov, M. G. Lenkovich, and N. D. Abdullaev, Khim. Geterotsikl. Soed., 503 (2002). [Chem. Heterocycl. Comp., 38, 438 (2002)].CrossRefGoogle Scholar
  11. 11.
    S. Toyoshima and N. Morishita, Yakugoku Zasshi, 86, 203 (1966).Google Scholar
  12. 12.
    J. Scam, J. Pharm. Sci., 58, 1043 (1969).CrossRefGoogle Scholar
  13. 13.
    R. Sh. Kuryazov, N. S. Mukhamedov, and Kh. M. Shakhidoyatov, Khim. Khim. Tekhnol., No. 1, 50 (2008).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • M. E. Karimova
    • 1
  • D. A. Dushamov
    • 1
    • 2
  • R. Sh. Kuryazov
    • 3
  • N. S. Mukhamedov
    • 3
    Email author
  1. 1.Khorezm Mamun AcademyKhorezm RegionRepublic of Uzbekistan
  2. 2.Al-Khorezm Urgench State UniversityUrgenchRepublic of Uzbekistan
  3. 3.Acad. S. Yunusov Institute of Chemistry of Plant SubstancesAcademy of Sciences of the Republic UzbekistanTashkentRepublic of Uzbekistan

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