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Synthesis of pyrazolines by the reactions ofα,β-enones with diazomethane and hydrazines (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The first representatives of pyrazolines were synthesized in the last century. These nitrogen-containing heterocyclic compounds became important in the development of different bioactive substances. For this reason, various procedures have been worked out for their synthesis. In the present article we summarize those synthetic methods providing 1- or 2-pyrazolines by the reactions of α,β-unsaturated ketones with diazomethane or hydrazine derivatives.

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References

  1. E. Fischer and O. Knövenagel, Ann.,239, 194 (1887).

    Google Scholar 

  2. K. v. Auwers and K. Müller, Ber.,41, 4230 (1908).

    Google Scholar 

  3. K. v. Auwers and A. Kreuder, Ber.,58, 1974 (1925).

    Google Scholar 

  4. K. v. Auwers and E. Cauer E., Ann.470, 284 (1929).

    Google Scholar 

  5. K. v. Auwers and F. König, Ann.,496, 27 (1932).

    Google Scholar 

  6. K. v. Auwers and O. Ungemach, Chem. Ber.,66, 1198 (1933).

    Google Scholar 

  7. K. v. Auwers and O. Ungemach, Chem. Ber.,66, 1205 (1933).

    Google Scholar 

  8. E. P. Kohler and L. L. Steele, J. Am. Chem. Soc.41, 1093 (1919).

    Google Scholar 

  9. L. I. Smith and W. B. Pings, J. Org. Chem.,2, 23 (1937).

    Google Scholar 

  10. W. M. Jones, J. Am. Chem. Soc.,81, 5153 (1959).

    Google Scholar 

  11. W. M. Jones and W. T. Tai, J. Org. Chem.,27, 1324 (1962).

    Google Scholar 

  12. C. G. Overberger and J. P. Anselme, J. Am. Chem. Soc.,84, 869 (1962).

    Google Scholar 

  13. T. V. Van Anken and K. L. Rinehart, Jr., J. Am. Chem. Soc.,84, 3736 (1962).

    Google Scholar 

  14. G. D. Kennedy, A. L. Baumstark, M. Dotrong, T. Thomas, and N. Narayanan, J. Heterocycl. Chem.,28, 1773 (1991).

    Google Scholar 

  15. K. Ramalingam, G. X. Thyvekikakath, K. D. Berlin, R. W. Chesnut, R. A. Brown, N. N. Durham, A. E. Ealick, and D. van der Helm, J. Med. Chem.,20, 847 (1977).

    Google Scholar 

  16. J. G. Lombardino and I. G. Otterrness, J. Med. Chem.,830 (1981).

  17. U. S. Pat. 3,624,102; R. E. Brown and J. Shavrel, Jr.; Chem. Abs.,76, 59618 (1972).

    Google Scholar 

  18. A. Weissberger, The Chemistry of Heterocyclic Compounds, Vol. 22, Wiley, New York (1967), p. 180.

    Google Scholar 

  19. H. v. Pechmann, Ber.,27, 1890 (1894).

    Google Scholar 

  20. E. Bergmann and F. J. Bergmann, Org. Chem.,3, 125 (1938).

    Google Scholar 

  21. A. N. Nesmeyanov and N. K. Kochetkov, Izv. Akad Nauk SSSR, Otd. Khim Nauk., 686 (1951).

  22. L. N. Owen and M. V. S. Sultanbawa, J. Chem. Soc., 3098 (1949).

  23. S. Y. Spencer and G. F. Wright, J. Am. Chem. Soc.,63, 2014 (1941).

    Google Scholar 

  24. J. Azzarello, Gazz. Chim. Ital.,36, 50 (1906).

    Google Scholar 

  25. L. I. Smith and K. L. Howard, J. Am. Chem. Soc.,65, 165 (1943).

    Google Scholar 

  26. G. V. S. Raju and K. S. Rao, Curr. Sci.,58, 1030 (1989).

    Google Scholar 

  27. A. Lévai and G. Tóth, Trends in Heterocyclic Chemistry,4, 89 (1995).

    Google Scholar 

  28. S. G. Ghate, R. Kaushal, and S. S. Deshapande, J. Indian Chem. Soc.,27, 633 (1950).

    Google Scholar 

  29. A. Mustafa and A. M. Fleifel, J. Org. Chem.,24, 1470 (1959).

    Google Scholar 

  30. G. H. Sayed and N. Kjosen, Indian J. Chem.,19B, 980 (1980).

    Google Scholar 

  31. L. A. Aleksandrova, N. A. Dorofeeva, A. V. Chernova, and V. K. Khairullin, Zh. Org. Khim.,14, 1974 (1978).

    Google Scholar 

  32. A. L. Tökés, A. Szöllösy, G. Tóth, and A. Lévai, Acta Chim. Hung.,112, 335 (1983).

    Google Scholar 

  33. A. Lévai, Monatsh. Chem.,126, 1245 (1995).

    Google Scholar 

  34. A. Lévai, Z. Cziáky, J. Jekö, and Z. Szabó, Indian J. Chem.,35B, 1091 (1996).

    Google Scholar 

  35. A. Mustafa and M. K. Hilmy, J. Chem. Soc., 3254 (1951).

  36. J. Kamecki, W. Perka, and L. Pijewska, Polish J. Chem.,59, 285 (1985).

    Google Scholar 

  37. L. Pijewska, J. Kamecki, and W. Perka-Karolczak, Pharmazie.,48, 254 (1993).

    Google Scholar 

  38. G. Tóth, A. Szöllösy, A. Lévai, and G. Kotovych, J. Chem. Soc. Perkin Trans. II, 1895 (1986).

    Google Scholar 

  39. G. Tóth, A. Lévai, and H. Duddeck, Magn. Reson. Chem.,30, 235 (1992).

    Google Scholar 

  40. G. Tóth, A. Lévai, A. Szöllösy, and H. Duddeck, Tetrahedron,49, 863 (1993).

    Google Scholar 

  41. K. v. Auwers and H. Voss, Ber.,42, 4411 (1909).

    Google Scholar 

  42. N. Kishner and J. Russ. Phys. Chem. Soc.,45, 949 (1913).

    Google Scholar 

  43. K. v. Auwers and P. Heimke, Ann.458, 186 (1927).

    Google Scholar 

  44. K. v. Auwers and E. Lömmerhirt, Ber.,54, 1000 (1921).

    Google Scholar 

  45. L. C. Raiford and J. B. Entrikin, J. Am. Chem. Soc.,55, 1125 (1933).

    Google Scholar 

  46. L. C. Raiford and W. J. Peterson, J. Org. Chem.,1, 544 (1936).

    Google Scholar 

  47. H. B. Nisbert, J. Chem. Soc., 1237 (1938).

  48. L. C. Raiford and G. V. Gundy, J. Org. Chem.,3, 265 (1938).

    Google Scholar 

  49. R. H. Wiley, C. H. Jarboe, F. N. Hayes, E. Hansbury, J. T. Nielsen, P. X. Callahan, and M. C. Sellars, J. Org. Chem.,23, 732 (1958).

    Google Scholar 

  50. P. Venturella, A. Bellino, and S. Cusmano, Ann. Chim. (Rome),51, 34 (1961).

    Google Scholar 

  51. D. G. Pereyaslova, V. E. Bondarenko, and B. M. Krasovitskii, Khim. Geterotsikl. Soed., No. 1, 114 (1969).

    Google Scholar 

  52. S. P. Sachchar and A. K. Singh, J. Indian Chem. Soc.,62, 142 (1985).

    Google Scholar 

  53. C. Gao and A. S. Hay, Synth. Commun.,25, 1877 (1995).

    Google Scholar 

  54. A. S. R. Anjaneyulu, Rani G. Sudha, Annapurna K. Gowri, K. Mallavadhani, and Y. L. N. Murthy, Indian J. Chem.,34B, 933 (1995).

    Google Scholar 

  55. S. A. Basaif, H. A. Albar, and H. M. Faidallah, Indian J. Heterocycl. Chem.,5, 121 (1995).

    Google Scholar 

  56. O. M. O. Habib, A. M. Khalil, E. M. Kandeel, and E. B. Abdalla, Rev. Roum. Chim.,31, 629 (1986).

    Google Scholar 

  57. A. E. A. Sammour, Tetrahedron.,20, 1067 (1964).

    Google Scholar 

  58. H. Ferres, M. S. Hamdam, and W. R. Jackson, J. Chem. Soc. (B)., 1892 (1971).

  59. Y. A. Al-Farkh, F. H. Al-Hajjar, F.S. Al-Shamali, and H. S. Hammond, Chem. Pharm. Bull.,27, 257 (1979).

    Google Scholar 

  60. N. Bauer and H. Dieterle, Ber.,44, 2697 (1911).

    Google Scholar 

  61. N. Kishner, J. Russ. Phys. Chem.,47, 1819 (1915).

    Google Scholar 

  62. F. Straus, Ber.,51, 1457 (1918).

    Google Scholar 

  63. E. P. Kohler and L. L. Steele, J. Am. Chem. Soc.,41, 1105 (1919).

    Google Scholar 

  64. L. C. Raiford and R. H. Manley, J. Org. Chem.,5, 590 (1940).

    Google Scholar 

  65. K. Freudenberg and W. Stoll, Ann.,440, 38 (1924).

    Google Scholar 

  66. F. G. Weber, K. Brosche, C. Seedorf, and A. Rinow, Monatsh. Chem.,100, 1924 (1969).

    Google Scholar 

  67. M. G. Joshi and K. N. Wadodkar, Indian J. Chem.,20B, 1090 (1981).

    Google Scholar 

  68. T. C. Sharma, S. R. Pawar, and N. I. Reddy, Acta Chim. Hung.,112, 159 (1983).

    Google Scholar 

  69. B. S. Holla and K. V. Udupa, Indian J. Chem.,29B, 887 (1990).

    Google Scholar 

  70. O. Widman, Ber.,49, 477 (1916).

    Google Scholar 

  71. O. Widman, Ber.,49, 2778 (1916).

    Google Scholar 

  72. H. Jörlander, Ber.,49, 2782 (1916).

    Google Scholar 

  73. S. Bodforss, Ber.,49, 2795 (1916).

    Google Scholar 

  74. S. Bodforss, Ber.,51, 192 (1918).

    Google Scholar 

  75. G. Litkei, A. Neubauer, and R. Bognár, Magy. Kém. Foly.,78, 359 (1972).

    Google Scholar 

  76. A. Neubauer, G. Litkei, and R. Bognár, Tetrahedron.,28, 3241 (1972).

    Google Scholar 

  77. K. M. Ghoniem, M. M. Badran, M. A. Shaaban, and S. El-Meligie, Egypt J. Pharm. Sci.,29, 563 (1988).

    Google Scholar 

  78. C. Dupuy and J. J. Luche, Tetrahedron.,45, 3437 (1989).

    Google Scholar 

  79. F. Kállay, G. Janzsó, and I. Koczor, Tetrahedron.,21, 19 (1965).

    Google Scholar 

  80. F. Kállay, G. Janzsó, and I. Koczor Tetrahedron.,21, 3037 (1965).

    Google Scholar 

  81. F. Kállay, G. janzsó, and I. Koczor, Tetrahedron.,23, 4317 (1967).

    Google Scholar 

  82. F. Kállay, Recent Developments in the Chemistry of Natural Carbon Compounds.,5, 154 (1973).

    Google Scholar 

  83. A. E. Sammour and M. Elkasaby, J. Chem. U.A.R.,12, 1 (1969).

    Google Scholar 

  84. Mg. Joshi and K. N. Wadodkar, Indian J. Chem.,20B, 1089 (1981).

    Google Scholar 

  85. M. S. Paur, G. C. Rovnyak, A. I. Cohen, B. Toeplitz, J. Z. Gougoutas, J. Org. Chem.,44, 2513 (1979).

    Google Scholar 

  86. G. C. Rovnyak and V. Shu, J. Org. Chem.,44, 2518 (1979).

    Google Scholar 

  87. T. Loránd, D. Szabó, A. Földesi, L. Párkányi, A. Kálmán, and A. Neszmélyi, J. Chem. Soc., Perkin Trans. 1., 481 (1985).

    Google Scholar 

  88. W. I. Awad, M. F. Ismail, and A. H. Moustafa, U.A.R. J. Chem.,14, 561 (1971).

    Google Scholar 

  89. Ger. Offen. 2520171, C. F. Turk; Chem. Abs.,84, 74261 (1976).

    Google Scholar 

  90. U. S. Pat. 3,969,527; J. Krapcho and J. Schwartz; Chem. Abs.,85, 77415 (1976).

    Google Scholar 

  91. N. R. El-Rayyes and A. Al-Jawhary, J. Heterocycl. Chem.,23, 135 (1986).

    Google Scholar 

  92. N. R. El-Rayyes and N. H. Bahtiti, J. Heterocycl. Chem.,26, 209 (1989).

    Google Scholar 

  93. A. Szöllösy, G. Tóth, T. Loránd, T. Kónya, F. Aradi, and A. Lévai, J. Chem. Soc. Perkin Trans. II, 489 (1991).

    Google Scholar 

  94. H. M. Faidallah and M. S. I. Makki, J. Chinese Chem. Soc.,41, 585 (1994).

    Google Scholar 

  95. T. Loránd, F. Aradi, A. Szöllösy, C. Toth, and T. Kónya, Monatsh. Chem.,127, 971 (1996).

    Google Scholar 

  96. A. Lévai, A. Szöllösy, and G. Tóth, J. Chem. Res. (S)., 392 (1985).

  97. A. Lévai, G. Tóth, and A. Szöllösy, Stud. Org. Chem. (Amsterdam),23, 47 (1986).

    Google Scholar 

  98. N. K. Sangwan and S. N. Rastogi, Indian J. Chem.,20B, 135 (1981).

    Google Scholar 

  99. N. K. Sangwan, J. Chem. Res. (S), 22 (1987).

  100. G. Tóth, A. Szöllösy, T. Loránd, T. Kónya, D. Szabó, A. Földesi, and A. Lévai, J. Chem. Soc. Perkin Trans. II, 319 (1989).

    Google Scholar 

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  1. Albert Lévai
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Department of Organic Chemistry, Kossuth Lajos University, Egyetem ter I, H 4010 Debrecen, Hungary. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 747–759, June, 1997.

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Lévai, A. Synthesis of pyrazolines by the reactions ofα,β-enones with diazomethane and hydrazines (review). Chem Heterocycl Compd 33, 647–659 (1997). https://doi.org/10.1007/BF02291794

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