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Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 818–822 | Cite as

Huisgen reaction of nitrile oxides and nitrile imines leading to isoxazoline and pyrazole-4,6-diones

  • J. Kaur
  • B. Singh
  • K. K. Singal
Article

Abstract

Huisgen reaction of nitrile oxides and nitrile imines generated in situ in the presence of N-benzylmaleimide afforded regiospecifically the corresponding cis-3-aryl-5-benzyl-3a,4,6,6atetrahydro-4H, 6H-pyrrolo[3,4-d]isoxazoline-4,6-diones and cis-3-aryl-5-benzyl-1-(2′,4′-dibromophenyl)-3a, 4,6,6a-tetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-diones in good yield.

Keywords

N-benzylmaleimide nitrile imines nitrile oxide Huisgen reaction regiospecific 

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References

  1. 1.
    K. V. Gothelf and K. A. Jorgensen, Chem. Rev., 98, 863 (1998).CrossRefGoogle Scholar
  2. 2.
    A. Banerji, J. Indian Chem. Soc., 77, 637 (2000).Google Scholar
  3. 3.
    W. Carruthers, in: Cycloaddition Reactions in Organic Synthesis, Pergamon Press, New York, 1990, p. 269.Google Scholar
  4. 4.
    J. J. Tufariello, in: 1,3-Dipolar Cycloadditions Chemistry, A. Padwa (Ed.), Wiley-Intersci., New York, 1984, vol. 2, Ch. 9, p. 83.Google Scholar
  5. 5.
    K. B. G. Torsell, in: Nitrile oxides, Nitrones and Nitronates in Organic Synthesis, H. Feuer (Ed.), VCH Publ. Inc, New York, 1988.Google Scholar
  6. 6.
    P. Grunanger and P. Vita-Finzi, in: Chemistry of Heterocyclic Compounds, Vol. 49, Pt. 1, Isoxazoles, E. C. Taylor, Weissberger (editors), Wiley, New York, 1991.Google Scholar
  7. 7.
    A. Rastelli, R. Gandolfi, and M. S. Amade, J. Org. Chem., 63, 7425 (1998).CrossRefGoogle Scholar
  8. 8.
    J. E. T. Corrie, J. Chem. Soc., Perkin Trans. 1, 2975 (1994).Google Scholar
  9. 9.
    K. D. Janda, J. A. Ashley, T. M. Jones, D. A. McLeod, D. M. Schloeder, and M. I. Weinhouse, J. Am. Chem. Soc., 112, 8886 (1990).CrossRefGoogle Scholar
  10. 10.
    G. Matocsy, M. Nadasi, and V. Adriska, Pesticide Chemistry, Akad. Kiado, Budapest, 1988.Google Scholar
  11. 11.
    N. Tottori, M. Ueda, O. Kirino, S. Oba, A. Fujinami, T. Kato, and T. Oaki, Jpn. Kokai, 74, 124225 (1975); Chem. Abstr., 82, 150501 (1975).Google Scholar
  12. 12.
    R. Grigg, S. Surendrakumar, S. Thianpatanagul, and D. J. Vipond, J. Chem. Soc., Perkin Trans. 1, 2693 (1988).Google Scholar
  13. 13.
    S. W. Baldwin, P. Greenspan, C. Alaimo, and A. T. McPhail, Tetrahedron Lett., 32, 5877 (1991).CrossRefGoogle Scholar
  14. 14.
    M. Konopikova, L. Fisera, and N. Pronayova, Collect. Czech. Chem. Commun., 57, 1521 (1991).CrossRefGoogle Scholar
  15. 15.
    V. Ondrus and L. Fisera, Molecules, 2, 49 (1997).CrossRefGoogle Scholar
  16. 16.
    P. W. Groundwater, M. Nyerges, I. Fejes, D. E. Hibbs, D. Bendell, R. J. Anderson, A. McKillop, and T. Sharif, W. Zhang, ARKIVOC, 1, 684 (2000).Google Scholar
  17. 17.
    E. Rajanarendar, M. Srinivas, and D. Karunakar, Indian J. Chem., 42, 1997 (2003).Google Scholar
  18. 18.
    U. A. R. Al-Timari, L. Fisera, and N. Pronayova, Collect. Czech. Chem. Commun., 57, 1982 (1992).CrossRefGoogle Scholar
  19. 19.
    E. Rajanarendar, Md. Afzal, and K. Ramu, Indian J. Chem., 42, 927 (2003).Google Scholar
  20. 20.
    N. Singh and K. Krishan, Indian J. Chem., 11, 1076 (1973).Google Scholar
  21. 21.
    N. Singh and K. Krishan, Tetrahedron Lett., 2711 (1973).Google Scholar
  22. 22.
    N. Singh and K. Krishan, Bull. Acad. Sci. USSR, 4, 908 (1974).Google Scholar
  23. 23.
    M. Rai, K. Krishan, and A. Singh, Indian J. Chem., 15, 848 (1977).Google Scholar
  24. 24.
    M. Rai, K. Krishan, J. Singh, and A. Singh, Indian J. Chem., 15, 1041 (1977).Google Scholar
  25. 25.
    M. Rai, K. Krishan, and A. Singh, J. Indian Chem. Soc., 58, 1111 (1981).Google Scholar
  26. 26.
    K. Krishan, A. Singh, B. Singh, and S. Kumar, Synth. Commun., 14, 219 (1984).Google Scholar
  27. 27.
    K. Krishan, A. Singh, and B. Singh, Indian J. Chem., 23, 620 (1984).Google Scholar
  28. 28.
    K. Krishan and B. Singh, Synth. Commun., 14, 1047 (1984).Google Scholar
  29. 29.
    K. Krishan and B. Singh, Synth. Commun., 15, 829 (1985).Google Scholar
  30. 30.
    K. K. Singal, Chem. Ind., 11, 761 (1985).Google Scholar
  31. 31.
    K. Krishan, B. Singh, and B. Raj, Synth. Commun., 23, 107 (1993).Google Scholar
  32. 32.
    K. K. Singal, Synth. Commun., 26, 3571 (1996).Google Scholar
  33. 33.
    K. K. Singal and R. Giare, Indian J. Heterocyclic Chem., 8, 121 (1998).Google Scholar
  34. 34.
    K. K. Singal and J. Kaur, Indian J. Heterocyclic Chem., 8, 117 (1998).Google Scholar
  35. 35.
    K. K. Singal and J. Kaur, Indian J. Heterocyclic Chem., 8, 249 (1999).Google Scholar
  36. 36.
    K. Krishan, B. Singh, and B. Raj, Synth. Commun., 29, 911 (1999).Google Scholar
  37. 37.
    K. K. Singal and J. Kaur, Indian J. Heterocyclic Chem., 9, 103 (1999).Google Scholar
  38. 38.
    K. K. Singal and J. Kaur, Chem. Environ. Res., 9, 47 (2000).Google Scholar
  39. 39.
    K. K. Singal and J. Kaur, J. Indian Council of Chemists, 17, 16 (2001).Google Scholar
  40. 40.
    J. Kaur, B. Singh, and K. K. Singal, Indian J. Chem., 44, 1476 (2005).Google Scholar
  41. 41.
    J. Kaur, B. Singh, and K. K. Singal, J. Indian Chem. Soc., 82, 1011 (2005).Google Scholar
  42. 42.
    C. Grundmann and R. Richer, J. Org. Chem., 25, 546 (1960).CrossRefGoogle Scholar
  43. 43.
    K. C. Liu, B. R. Shelton, and R. K. Howe, J. Org. Chem., 45, 3916 (1980).CrossRefGoogle Scholar
  44. 44.
    B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith, and A. R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, 1989, Vol. 5, p. 1084.Google Scholar
  45. 45.
    A. Quilico and P. Grunanger, Gazz. Chim. Ital., 80, 479 (1950); Chem. Abstr., 45, 3836 (1951).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • J. Kaur
    • 1
  • B. Singh
    • 2
  • K. K. Singal
    • 2
  1. 1.Department of ChemistryG.H.G. Khalsa College, Gurusar Sadhar, LudhianaPunjabIndia
  2. 2.Department of ChemistryPunjabi University, PatialaPunjabIndia

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