Russian Chemical Bulletin

, Volume 54, Issue 5, pp 1239–1244 | Cite as

Synthesis of substituted 1,2-di(alkylsulfonyl)indolizines. Molecular and crystal structure of 3-(4-fluorobenzoyl)-6-methyl-1,2-di(propylsulfonyl)indolizine

  • N. E. Dontsov
  • V. N. Nesterov
  • A. M. Shestopalov
  • V. P. Litvinov


The reactions of substituted pyridinium salts with E-1,2-di(alkylsulfonyl)-1,2-dichloroethenes proceed regiospecifically. Heating of these reagents in chloroform in the presence of a threefold excess of Et3N affords substituted 1,2-di(alkylsulfonyl)indolizines in high yields. The structures of the reaction products were confirmed by physicochemical methods, including X-ray diffraction.

Key words

1,2-di(alkylsulfonyl)indolizines 3-(4-fluorobenzoyl)-6-methyl-1,2-di(propylsulfonyl)indolizine pyridinium salts E-1,2-di(alkylsulfonyl)-1,2-dichloroethene pyridinium ylides X-ray diffraction study 


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  1. 1.
    The Merck Index, Ed. V. J. O'Neil, Merck and Co., Inc., Whitehouse Station, New York, 2001, 951.Google Scholar
  2. 2.
    A. E. Chichibabin, Ber. Dtsch.Chem. Ges., 1925, 58, 1706.Google Scholar
  3. 3.
    A. M. Shestopalov, Dr. Sc. (Chem.) Thesis, N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, 1991, 377 pp. (in Russian).Google Scholar
  4. 4.
    V. P. Litvinov, Zh. Org. Khim., 1995, 30, 1441 [Russ. J. Org. Chem., 1995, 30 (Engl. Transl.).Google Scholar
  5. 5.
    V. N. Nesterov, N. E. Dontsova, A. M. Shestopalov, Yu. T. Struchkov, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 1996, 7, 950 [Chem. Heterocycl. Compd., 1996, 7 (Engl. Transl.)].Google Scholar
  6. 6.
    The Chemistry of Heterocyclic Compounds. Vol. 59 . Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Eds A. Padwa and W. H. Pearson, John Wiley and Sons, Inc., New York, 2002, 940 pp.Google Scholar
  7. 7.
    A. M. Shestopalov, V. P. Litvinov, Yu. A. Sharanin, and G. E. Khoroshilov, Dokl. Akad. Nauk SSSR, 1990, 312, 1156 [Dokl. Chem., 1990 (Engl. Transl.)].Google Scholar
  8. 8.
    A. M. Shestopalov, V. P. Litvinov, L. A. Rodinovskaya, and Yu. A. Sharanin, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 146 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 129 (Engl. Transl.)].Google Scholar
  9. 9.
    A. M. Shestopalov, L. A. Rodinovskaya, Yu. A. Sharanin, and V. P. Litvinov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1630 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 1446 (Engl. Transl.)].Google Scholar
  10. 10.
    A. M. Shestopalov, L. A. Rodinovskaya, V. P. Litvinov, B. Buinitskii, and M. Mikolaichik, Dokl. Akad. Nauk, 1992, 323, 1116 [Dokl. Chem., 1992 (Engl. Transl.)].Google Scholar
  11. 11.
    A. M. Shestopalov, O. P. Bogomolova, L. A. Rodinovskaya, V. P. Litvinov, B. Bujnicki, M. Mikolajczyk, V. N. Nesterov, and Yu. T. Struchkov, Heteroatom. Chem., 1993, 4, 593.CrossRefGoogle Scholar
  12. 12.
    E. N. Prilezhaeva, N. E. Dontsova, N. P. Petukhova, and V. S. Bogdanov, Gazz. Chim. Ital., 1990, 120, 235.Google Scholar
  13. 13.
    F. N. Allen, O. Kennard, D. J. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1.Google Scholar
  14. 14.
    A. M. O'Connell and E. N. Maslen, Acta Crystallogr., 1967, 22, 134.CrossRefGoogle Scholar
  15. 15.
    R. J. Gillespie and I. Hargittai, The VSEPR Model of Molecular Geometry, Allyn and Bacon, 1991.Google Scholar
  16. 16.
    Z. Berkovitch-Yellin and L. Leiserowitz, Acta Crystallogr., 1984, B40, 159.Google Scholar
  17. 17.
    R. S. Rowland and R. Taylor, J. Phys. Chem., 1996, 100, 7384.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • N. E. Dontsov
    • 1
  • V. N. Nesterov
    • 2
  • A. M. Shestopalov
    • 1
  • V. P. Litvinov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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