Download PDF
Synthesis 2002(1): 0133-0137
DOI: 10.1055/s-2002-19313
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Syntheses of New CF3-containing Diazolopyrimidines

Arcady L. Krasovsky, Anton S. Hartulyari, Valentine G. Nenajdenko*, Elizabeth S. Balenkova
Department of Chemistry , Moscow State University , 119899 Moscow, Russia
Fax: +7(95)9328846; e-Mail: Nen@acylium.chem.msu.su;
Further Information

Publication History

Received 1 August 2001
Publication Date:
04 August 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

A new simple and efficient way to CF3-containing pyrimido[1,2-a]benzimidazole and pyrazolo[1,5-a]pyrimidines, by the reaction of 1,1,1-trifluoro-4-sulfonyl-but-3-ene-2,2-dioles 1a,b with aminoheterocycles is described. The influence of reaction conditions and nature of the aminoheterocycles on regiochemistry was investigated.

Key words

cycloaddition - heterocycles - pyrimido[1,2-a]benzimidazole - pyrazolo[1,5-a]pyrimidines - sulfones

    References

  • 1 Elnagdi MN. Elmoghayar MRH. Elgemeie GEH. In Advances in Heterocyclic Chemistry   Vol. 41:  Katritzky AR. Academic Press; New York: 1987.  p.320 
    Google Scholar
  • 2a Elnagdi MN. Elmoghayar MRH. Sadek KU . In Advances in Heterocyclic Chemistry   Vol. 48:  Katritzky AR. Academic Press; New York: 1990.  p.219 
    Google Scholar
  • 2b Elnagdi MN. Taha NH. Abd ElAllFM. Abdel-Motaleb RM. Mahmoud FF. Coll. Czech. Chem. Commun.  1988,  53:  1089 
    Google Scholar
  • 3 Bouillon J.-P. Janousek Z. Viehe HG. Tinant P. Declercq J.-P. J. Chem. Soc., Perkin Trans. 1.  1995,  2907 
    CrossrefGoogle Scholar
  • 4 Kawase M. Hirabayashi M. Saito S. Yamamoto K. Tetrahedron Lett.  1999,  40:  2541 
    CrossrefGoogle Scholar
  • 5 Balicki R. Nantka-Namirski P. Pol. J. Chem.  1980,  54:  2175 
    Google Scholar
  • 6 Rempfler H, and Duerr D. inventors; EP  337944.  ; Chem. Abstr., 1990, 112, 139043r
  • 7 Rempfler H, Duerr D, and Thummel RC. inventors; EP  337943.  ; Chem. Abstr., 1990, 112, 139044s
  • 8 Bajwa JS. Sykes PJ. J. Chem. Soc. Perkin Trans. 1.  1979,  3085 ; and references cited therein
    CrossrefGoogle Scholar
  • 9 Reiter J. Pongo L. Dyortsak P. Tetrahedron  1987,  43:  2497 
    CrossrefGoogle Scholar
  • 10 Greenhill JV. In Comprehensive Heterocyclic Chemistry   Part 4A, Vol. 5:  Potts KT. Pergamon Press; Oxford: 1984.  Chapt. 4.05. p.305 
    Google Scholar
  • 11 Kreutzberger A. Leger M. Heterocyclic Chem.  1981,  18:  1587 
    Google Scholar
  • 12 Novinson T. Hanson R. Dimmitt MK. Simon LN. Robins RK. O" Brien D. J. Med. Chem.  1974,  645 
    CrossrefGoogle Scholar
  • 13 Balicki R. Pol. J. Chem.  1981,  55:  1995 
    Google Scholar
  • 14 Imbach J.-L. Jacquier R. Vidal J.-L. Bull. Soc. Chim. Fr.  1970,  5:  1929 
    Google Scholar
  • 15 Huppatz JL. Aust. J. Chem.  1985,  38:  221 
    Google Scholar
  • 16 Bajwa JS. Sykes PJ. J. Chem. Soc. Perkin Trans. 1.  1979,  3085 
    CrossrefGoogle Scholar
  • 17 Elnagdi MH. Erian AW. Bull. Chem. Soc. Jpn.  1990,  63:  1854 
    Google Scholar
  • 18 Thomas A. Chakraborty M. Ila H. Junjappa H. Tetrahedron  1990,  46:  577 
    CrossrefGoogle Scholar
  • 19 Bajwa JS. Sykes PJ. J. Chem. Soc. Perkin Trans. 1.  1980,  1859 
    CrossrefGoogle Scholar
  • 20 Krasovsky AL. Nenajdenko VG. Balenkova ES. Tetrahedron  2001,  1:  1349 
    Google Scholar
  • 21 Nenajdenko VG. Krasovsky AL. Lebedev ML. Balenkova ES. Synlett  1997,  12:  1349 
    Article in Thieme ConnectGoogle Scholar
  • 23 Kirkpatrick WE. Okabe T. Hillyard IW. Robins RK. Dren AT. Novinson T. J. Med. Chem.  1977,  386 
    CrossrefGoogle Scholar
22

Krasovsky, A. L.; Nenajdenko, V. G.; Balenkova, E. S.; Synthesis 2001 in press.