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Russian Chemical Bulletin

, Volume 60, Issue 1, pp 153–156 | Cite as

3-Hydroxy- and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones: synthesis and reactions with alkylating and acylating agents

  • P. S. Khokhlov
  • V. N. Osipov
  • A. V. Roshchin
Full Articles

Abstract

Reactions of methyl 2-isothiocyanatobenzoate with hydroxylamine and alkoxyamines afforded earlier unknown 3-hydroxy-2-sulfanylquinazolin-4(3H)-one (1a) and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones (1b,c). Base-catalyzed reactions of compound 1a with alkyl halides were not regioselective, yielding O,S-dialkylation products. In the presence of acetic acid and sodium acetate, compound 1a was alkylated only at the S atom to give 2-alkylsulfanyl-3-hydroxyquinazolin-4(3H)-ones. Selective O-acylation of compound 1a at position 3 yielded 3-acyloxy-2-sulfanylquinazolin-4(3H)-ones.

Key words

quinazolinones 2-isothiocyanatobenzoate hydroxylamines cyclocondensation alkylation acylation 

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References

  1. 1.
    S. Eguchi; in Topics in Heterocyclic Chemistry, Ed. S. Eguchi, Springer, Berlin, 2006, 6, 113.Google Scholar
  2. 2.
    J. P. Michael, Nat. Prod. Rep., 2007, 24, 223.CrossRefGoogle Scholar
  3. 3.
    G. W. Rewcastle, in Comprehensive Heterocyclic Chemistry, Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Elsevier, Oxford, 2008, 8, 117.Google Scholar
  4. 4.
    D. J. Brown, in Chemistry of Heterocyclic Compounds, Ed. E. C. Taylor, John Wiley and Sons, Inc., New York, 1996, 55.CrossRefGoogle Scholar
  5. 5.
    RU Pat. 2 275 362, Byull. Izobret., 2006, 12; Chem. Abstrs, 2006, 144, 390940.Google Scholar
  6. 6.
    L. N. Tumey, D. Bom, B. Huck, E. Gleason, J. Wang, D. Silver, K. Brunden, S. Boozer, S. Rundlett, B. Sherf, S. Murphy, T. Dent, C. Leventhal, A. Bailey, J. Harrington, Y. L. Bennani, Bioorg. Med. Chem. Lett., 2005, 15, 277.CrossRefGoogle Scholar
  7. 7.
    T. P. Tran, E. L. Ellsworth, M. A. Stier, J. M. Domagala, H. D. H. Showalter, S. J. Gracheck, M. A. Shapiro, T. E. Joannides, R. Singh, Bioorg. Med. Chem. Lett., 2004, 14, 4405.CrossRefGoogle Scholar
  8. 8.
    V. Colotta, D. Catarzi, F. Varano, F. R. Calabri, G. Filac- chioni, C. Costagli, A. Galli, Bioorg. Med. Chem. Lett., 2004, 14, 2345; I. L. Dikii, O. S. Kris’kiv, V. P. Chernikh, L. A. Shemchuk, N. V. Dubinina, Visn. Farm. [Bull. Pharm.], 2006, 2, 64 (in Ukrainian).CrossRefGoogle Scholar
  9. 9.
    A. V. Kotov, V. V. Zakharychev, A. G. Smirnov, V. I. Fetis- ov, P. B. Gordeev, O. A. Luk’yanov, A. L. Chimishkyan, I. V. Martynov, Dokl. Akad. Nauk, 2001, 381, 694 [Dokl. Chem. (Engl. Transl.), 2001, 381].Google Scholar
  10. 10.
    P. N. Pohorgava, S. N. Singh, Egypt. J. Chem., 1972, 15, 495.Google Scholar
  11. 11.
    R. K. Saksena, A. Khan, Indian J. Chem., 1988, 27B, 295.Google Scholar
  12. 12.
    S. Senda, A. Suzui, Chem. Pharm. Bull., 1958, 6, 47Google Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • P. S. Khokhlov
    • 1
  • V. N. Osipov
    • 2
  • A. V. Roshchin
    • 1
  1. 1.N. N. Semenov Institute of Chemical PhysicsRussian Academy of SciencesMoscowRussian Federation
  2. 2.N. N. Blokhin Cancer Research CenterRussian Academy of Medical SciencesMoscowRussian Federation

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