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Russian Chemical Bulletin

, Volume 58, Issue 9, pp 1986–1990 | Cite as

A novel rearrangement in the system 3-[aryl(chloro)methyl]quinoxalin-2(1H)-one— α-picoline as a simple and efficient route to indolizin-2-ylbenzimidazoles

  • V. A. Mamedov
  • D. F. Saifina
  • A. T. Gubaidullin
  • A. F. Saifina
  • I. Kh. Rizvanov
  • V. R. Ganieva
Full Articles

Abstract

A reaction of 3-(α-chlorobenzyl)quinoxalin-2(1 H)-one with α-picoline gives 2-(3-phenyl-indolizin-2-yl)benzimidazole as a result of a ring-contracting rearrangement involving the fragment C(2)—C(3)—C(Cl)Ph of the quinoxaline system and the fragment N=CH—Me of the α-picoline system. Possible pathways of this reaction are discussed.

Keywords 3-(α-chlorobenzyl)quinoxalin-2(1 H)-one α-picoline ring contraction rearrangement 2-(3-phenylindolizin-2-yl)benzimidazole IR spectroscopy 1H NMR spectroscopy X-ray diffraction analysis 

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References

  1. 1.
    N. G. Brink, F. W. Holly, C. H. Shunk, E. W. Peel, J. J. Cahill, K. Folkers, J. Am. Chem. Soc., 1950, 72, 1866; D. E. Wolf, W. H. Jones, J. Valiant, K. Folkers, J. Am. Chem. Soc. 1950, 72, 2820.CrossRefGoogle Scholar
  2. 2.
    S. Salluja, R. Zou, J. C. Drach, L. B. Townsend, J. Med. Chem., 1996, 39, 881.CrossRefGoogle Scholar
  3. 3.
    H. Zarrinmayeh, D. M. Zimmerman, B. E. Cantrell, D. A. Schober, R. F. Bruns, S. L. Gackenheimer, P. L. Oznstein, P. A. Hipskind, T. C. Britton, D. R. Gehlert, Bioorg. Med. Chem. Lett., 1999, 9, 647.CrossRefGoogle Scholar
  4. 4.
    I. Antonini, F. Claudi, G. Cristalli, P. Franchetti, M. Grifantini, S. Martelli, J. Med. Chem., 1988, 31, 260.CrossRefGoogle Scholar
  5. 5.
    E. B. Skibo, W. G. Schulz, J. Med. Chem., 1993, 36, 3050.CrossRefGoogle Scholar
  6. 6.
    R. Zhou, E. B. Skibo, J. Med. Chem., 1996, 39, 4321.CrossRefGoogle Scholar
  7. 7.
    W. A. Craigo, B. W. LeSueur, E. B. Skibo, J. Med. Chem., 1999, 42, 3324.CrossRefGoogle Scholar
  8. 8.
    R. Cedillo-Rivera, O. Muñoz, J. Med. Microbiol., 1992, 37.Google Scholar
  9. 9.
    B. Chavez, R. Cedillo-Rivera, A. Martinez-Palomo, J. Protozool., 1992, 39, 510.Google Scholar
  10. 10.
    S. D. Fears, O’Jare, J. Antimicrob. Agents Chemother., 1998, 32, 144.Google Scholar
  11. 11.
    A. A. Spasov, I. N. Yoshitsa, L. I. Bugaeva, V. A. Anisimova, Pharm. Chem. J., 1999, 33, 232.CrossRefGoogle Scholar
  12. 12.
    P. J. Taggart, L. R. Cooke, P. C. Mercer, M. W. Shaw, Crop Prot., 1998, 17, 727.CrossRefGoogle Scholar
  13. 13.
    E. S. Lane, J. Chem. Soc., 1955, 1079.Google Scholar
  14. 14.
    C. T. Brain, S. A. Brunton, Tetrahedron Lett., 2002, 43, 1893.CrossRefGoogle Scholar
  15. 15.
    H. Wagner, J. Org. Chem., 1944, 9, 31.CrossRefGoogle Scholar
  16. 16.
    V. A. Mamedov, I. A. Nuretdinov, F. G. Sibgatullina, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 1412 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 1292].Google Scholar
  17. 17.
    A. A. Kalinin, O. G. Isaikina, V. A. Mamedov, Khim. Geterotsikl. Soedin., 2004, 1741 [Chem. Heterocycl. Compd. (Engl. Transl.), 2004, 40].Google Scholar
  18. 18.
    V. A. Mamedov, A. A. Kalinin, A. T. Gubaidullin, I. A. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2007, 2386 [Russ. Chem. Bull., Int. Ed., 2007, 56, 2471].Google Scholar
  19. 19.
    V. A. Mamedov, D. F. Saifina, I. Kh. Rizvanov, A. T. Gubaidullin, Tetrahedron Lett., 2008, 49, 4647.Google Scholar
  20. 20.
    G. M. Sheldrick, SADABS, Program for Empirical X- ray Absorption Correction, Bruker-Nonius, 1990–2004.Google Scholar
  21. 21.
    G. M. Sheldrick, SHELXTL v.6.12, Structure Determination Software Suite, Bruker AXS, Madison (Wisconsin, USA), 2000.Google Scholar
  22. 22.
    L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837.CrossRefGoogle Scholar
  23. 23.
    APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31 A), Bruker Advanced X- ray Solutions, Bruker AXS, Madison (Wisconsin, USA), 2006.Google Scholar
  24. 24.
    A. L. Spek, Acta Crystallogr., Sect. A, 1990, 46, 34.Google Scholar

Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • V. A. Mamedov
    • 1
  • D. F. Saifina
  • A. T. Gubaidullin
  • A. F. Saifina
  • I. Kh. Rizvanov
  • V. R. Ganieva
  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Research Center of the Russian Academy of SciencesKazanRussian Federation

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