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Russian Chemical Bulletin

, Volume 55, Issue 1, pp 123–136 | Cite as

Synthesis of annulated oxazolidinones as potential precursors of cyclic cis-β-amino alcohols

  • Yu. B. Chudinov
  • S. B. Gashev
  • N. B. Chernysheva
  • V. V. Semenov
Article

Abstract

A simple method for the synthesis of annulated 1,3-oxazolidin-2-ones from accessible ketones, acetylene, and carbon dioxide was developed. If their molecules contain arylalkyl substituents, intramolecular cyclization in acidic media gave rise to fused heterocyclic systems in high yields. The effects of the substituents in positions 3 and 5 of the oxazolidine ring on the regioselectivity of this cyclization were studied. The possibilities of converting oxazolidinones into cyclic cis-β-amino alcohols were studied.

Key words

chiral auxiliary reagents β-amino alcohols carbonates dioxolanones 1,3-oxazolidin-2-ones amidoalkylation tetrahydronaphthalenes tetrahydroisoquinolines cyclization 

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References

  1. 1.
    K. Saigo, Yu. Khashimoto, and A. Sudo, Zh. Org. Khim., 1996, 32, 249 [J. Org. Chem. USSR, 1996, 32 (Engl. Transl.)].Google Scholar
  2. 2.
    K. Maruoka, S. Saito, and H. Yamamoto, J. Am. Chem. Soc., 1995, 117, 1165.CrossRefGoogle Scholar
  3. 3.
    S. Sugiyama, K. Morishita, M. Chiba, and K. Ishii, Heterocycles, 2002, 57, 637.CrossRefGoogle Scholar
  4. 4.
    I. Yu. Titov, Yu. B. Chudinov, N. B. Chernysheva, A. A. Bogolyubov, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 2006, 548 [Russ. Chem. Bull., Int. Ed., 2006, 55, No. 3].Google Scholar
  5. 5.
    N. B. Chernysheva, A. A. Bogolyubov, V. V. Murav’ev, V. V. Elkin, and V. V. Semenov, Khim. Geterotsikl. Soedin., 2000, 1409 [Chem. Heterocycl. Compd., 2000, 36 (Engl. Transl.)].Google Scholar
  6. 6.
    Germ. Pat. 1.098.953; Chem. Abstrs, 1962, 56, 2453.Google Scholar
  7. 7.
    N. B. Chernysheva, A. A. Bogolyubov, and V. V. Semenov, Khim. Geterotsikl. Soedin., 1999, 241 [Chem. Heterocycl. Compd., 1999, 35 (Engl. Transl.)].Google Scholar
  8. 8.
    H. Huang, J. Org. Chem., 2004, 24, 1388.Google Scholar
  9. 9.
    F. M. Menger, Tetrahedron, 1983, 39, 1013.CrossRefGoogle Scholar
  10. 10.
    A. M. Moiseenkov, V. A. Dragan, V. V. Veselovskii, B. A. Cheskis, N. A. Shpiro, and A. S. Shashkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1361 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 1226 (Engl. Transl.)].Google Scholar
  11. 11.
    V. Arivo, R. York, and R. F. Polany, Can. J. Chem., 1977, 55, 24.CrossRefGoogle Scholar
  12. 12.
    A. G. Sakhabutdinov and A. G. Usmanova, Zh. Org. Khim., 1988, 24, 1691 [J. Org. Chem. USSR, 1988, 24 (Engl. Transl.)].Google Scholar
  13. 13.
    A. Hoffman, J. Am. Chem. Soc., 1929, 51, 2542.CrossRefGoogle Scholar
  14. 14.
    O. Yu. Magidson and G. A. Garkusha, Zh. Obshch. Khim., 1941, 11, 339 [J. Gen. Chem. USSR, 1941, 11 (Engl. Transl.)].Google Scholar
  15. 15.
    A. A. Ponomarev and Z. V. Til’, Zh. Obshch. Khim., 1957, 27, 1075 [J. Gen. Chem. USSR, 1957, 27 (Engl. Transl.)].Google Scholar
  16. 16.
    C. L. Hewett, J. Chem. Soc., 1940, 293.Google Scholar
  17. 17.
    J. Rigaudy and M. Lachgar, Bull. Soc. Chim. Fr., 1994, 131, 177.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Yu. B. Chudinov
    • 1
  • S. B. Gashev
    • 1
  • N. B. Chernysheva
    • 1
  • V. V. Semenov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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