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Russian Chemical Bulletin

, Volume 52, Issue 3, pp 674–678 | Cite as

Regioselective synthesis of cis- and trans-2,4,5-triarylimidazolines and 2,4,5-triarylimidazoles from available reagents

  • N. A. Lozinskaya
  • V. V. Tsybezova
  • M. V. Proskurnina
  • N. S. Zefirov
Article

Abstract

Novel data were obtained concerning the reaction of aromatic aldehydes with ammonia. A preparative method for the synthesis of new substituted 1,3,5-triaryl-2,4-diazapenta-1,4-dienes was developed. These products are the starting reactants for syntheses of cis- and trans-2,4,5-triaryl-2-imidazolines and 2,4,5-triarylimidazoles.

aromatic aldehydes 1,3,5-triaryl-2,4-diazapenta-1,4-dienes hydrobenzamide imidazolines imidazoles 

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References

  1. 1.
    A. Laurent, C. R. Ann., 1837, 21, 130.Google Scholar
  2. 2.
    A. Laurent, C. R. Acad. Sci. (Paris), 1844, 19, 353; R. B. Bates, D. W. Gosselink, and J. A. Kaczynski, Tetrahedron Lett., 1967, 205.Google Scholar
  3. 3.
    L. Ekman, Ann., 1859, 112; H. L. Snape and A. Broke, Trans. Chem. Soc. (London), 1899, 77, 208.Google Scholar
  4. 4.
    S. N. Svetozarskii, E. N. Zil´berman, and A. N. Finkel´shtein, Zh. Obshch. Khim., 1961, 31(5), 1717 [J. Gen. Chem., 1961, 31 (Engl. Transl.)].Google Scholar
  5. 5.
    O. F. Williams and J. C. Bailar, J. Am. Chem. Soc., 1959, 81, 4466; H. H. Strain, J. Am. Chem. Soc., 1927, 49, 1558; D. H. Hunter and S. K. Sim, Can. J. Chem., 1972, 50, 669.Google Scholar
  6. 6.
    D. Lucet, Le Gall Thierry, and C. Mioskowski, Angew. Chem., Int. Ed., 1998, 37, 2580.Google Scholar
  7. 7.
    E. J. Corey and F. N. Kuhle, Tetrahedron Lett., 1997, 38, 8631.Google Scholar
  8. 8.
    D. H. Hunter and S. K. Sim, J. Am. Chem. Soc., 1969, 91, 6202.Google Scholar
  9. 9.
    A. T. Nielsen, R. L. Atkins, D. W. Moore, R. Scott, D. Mallory, and J. M. LaBerge, J. Org. Chem., 1973, 38, 3288.Google Scholar
  10. 10.
    K. Saigo, N. Kubota, S. Takebayashi, and M. Hasegawa, Bull. Chem. Soc. Jpn., 1986, 59, 931.Google Scholar
  11. 11.
    V. R. Sandel, S. V. McKinley, and H. H. Freedman, J. Am. Chem. Soc., 1968, 90, 495.Google Scholar
  12. 12.
    J. Nicholson and R. Porets, Can. J. Chem., 1965, 43, 3067.Google Scholar
  13. 13.
    M. L. Larter, M. Phillips, F. Ortega, G. Aguirre, R. Somanathan, and P. J. Walsh, Tetrahedron Lett., 1998, 39, 4785.Google Scholar
  14. 14.
    A. Kamal, A. Ahmad, and A. A. Qureshi, Tetrahedron Lett., 1963, 19, 869.Google Scholar

Copyright information

© Plenum Publishing Corporation 2003

Authors and Affiliations

  • N. A. Lozinskaya
    • 1
  • V. V. Tsybezova
    • 1
  • M. V. Proskurnina
    • 1
  • N. S. Zefirov
    • 1
  1. 1.Department of ChemistryM. V. Lomonosov Moscow State University, Leninsky GoryMoscowRussian Federation

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