Advertisement

Chemistry of Heterocyclic Compounds

, Volume 50, Issue 9, pp 1214–1243 | Cite as

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

  • I. V. LedenyovaEmail author
  • V. V. Didenko
  • Kh. S. Shikhaliev
Article

The methods of synthesis, structure, reactivity, and synthetic utility of pyrazole-3(5)-diazonium salts are reviewed here for the first time, with emphasis on heterocyclization reactions of these compounds.

Keywords

fused pyrazole systems pyrazole-3(5)-diazonium salts azo coupling heterocyclization 

References

  1. 1.
    L. C. Behr, R. Fusco, and C. H. Jarboe, in: R. H. Wiley (editor), The Сhemistry of Heterocyclic Compounds, Vol. 22, Wiley, New York (1967), p. 888.Google Scholar
  2. 2.
    R. N. Butler, Chem. Rev., 75, 241 (1975).Google Scholar
  3. 3.
    K. Schofield, M. R. Grimmett, and B. R. T. Keene (editors), Heteroaromatic Nitrogen Compounds. The Azoles, Cambridge University Press (1976), p. 437.Google Scholar
  4. 4.
    Stevens M. F. G., in: G. P. Ellis and G. B. West (editors), Progress in Medicinal Chemistry, Vol. 13, North-Holland Publishing Company, Toronto (1976), p. 205.Google Scholar
  5. 5.
    M. Tišler and B. Stanovnik, Chem. Heterocycl. Compd., 16, 443 (1980). [Khim. Geterotsikl. Soedin., 579 (1980).]Google Scholar
  6. 6.
    H. Dorn, Chem. Heterocycl. Compd., 17, 1 (1981). [Khim. Geterotsikl. Soedin., 3 (1981)].Google Scholar
  7. 7.
    M. H. Elnagdi, E. M. Zayed, and S. Abdou, Heterocycles, 19, 559 (1982).Google Scholar
  8. 8.
    M. H. Elnagdi, F. M. Abdel-Galil, B. Y. Riad, and G. E. H. Elgemeie, Heterocycles, 20, 2437 (1983).Google Scholar
  9. 9.
    E. A. A. Hafez, N. M. Abed, M. R. H. Elmoghayer, and A. G. A El-Agamey, Heterocycles, 22, 1821 (1984).Google Scholar
  10. 10.
    A. Engel, in: D. Klamann (editor), Houben-Weyl. Methoden der Organischen Chemie, 4th ed., Bd. E-16a, Teil 2, Georg Thieme Verlag, Stuttgart (1990), S. 1052.Google Scholar
  11. 11.
    M. H. Elnagdi, M. R. H. Elmoghayer, and K. U. Sadek, in: A. R. Katritzky (editor), Advances in Heterocyclic Chemistry, Vol. 48, Academic Press Inc., San Diego (1990), p. 223.Google Scholar
  12. 12.
    K. Makino, H. S. Kim, and Y. Kurasawa, J. Heterocycl. Chem., 36, 321 (1999).Google Scholar
  13. 13.
    T. M. A. Elmaati and F. M. El-Taweel, J. Heterocycl. Chem., 41, 109 (2004).Google Scholar
  14. 14.
    S. M. Riyadh, I. A. Abdelhamid, H. M. Ibrahim, H. M. Al-Matar, and M. H. Elnagdi, Heterocycles, 71, 2545 (2007).Google Scholar
  15. 15.
    G. Hajos and Z. Riedl, in: A. R. Katritzky (editor), Compr. Heterocycl. Chem. III, Vol. 11, Elsevier Ltd., Oxford (2008), p. 765.Google Scholar
  16. 16.
    V. L. Rusinov, E. N. Ulomskii, O. N. Chupakhin, and V. N. Charushin, Russ. Chem. Bull., Int. Ed., 57, 985 (2008). [Izv. Akad. Nauk, Ser. Khim., 967 (2008).]Google Scholar
  17. 17.
    H. F. Anwar and M. H. Elnagdi, ARKIVOC, i, 198 (2009).Google Scholar
  18. 18.
    J. M. Tedder, in: A. R. Katritzky and A. J. Boulton (editors), Advances in Heterocyclic Chemistry, Vol. 8, Academic Press, New York (1967), p. 1.Google Scholar
  19. 19.
    M. Tisler and B. Stanovnik, Heterocycles, 4, 1115 (1976).Google Scholar
  20. 20.
    G. Cirrincione, A. M. Almerico, E. Aiello, and G. Dattolo, in: A. R. Katritzky (editor), Advances in Heterocyclic Chemistry, Vol. 48, Academic Press Inc., San Diego (1990), p. 65.Google Scholar
  21. 21.
    J. O. Subbotina, E. V. Sadchikova, V. A. Bakulev, W. M. F. Fabian, and R. Herges, Int. J. Quant. Chem., 107, 2479 (2007).Google Scholar
  22. 22.
    H. Reimlinger, A. Overstraeten, and H. G. Viehe, Chem. Ber., 94, 1036 (1961).Google Scholar
  23. 23.
    E. V. Sadchikova and V. S. Mokrushin, Russ. Chem. Bull., Int. Ed., 54, 354 (2005). [Izv. Akad. Nauk, Ser. Khim., 348 (2005).]Google Scholar
  24. 24.
    H. Lund, J. Chem. Soc., 418 (1935).Google Scholar
  25. 25.
    R. P. Brint, D. J. Coveney, F. L. Lalor, G. Ferguson, M. Parvez, and P. Y. Siew, J. Chem. Soc., Perkin Trans. 2, 139 (1985).Google Scholar
  26. 26.
    A. E. Hammadi, M. E. Mouhtadi, R. Notario, A. Werner, and J. Elguero, J. Chem. Soc., Perkin Trans. 2, 379 (1995).Google Scholar
  27. 27.
    X.-M. Zou, F.-Z. Hu, and H.-Z. Yang, Chin. J. Struct. Chem., 23, 149 (2004).Google Scholar
  28. 28.
    O. Seidel, J. Prakt. Chem., 58, 129 (1898).Google Scholar
  29. 29.
    L. Knorr, Ber. Dtsch. Chem. Ges., 37, 3520 (1904).Google Scholar
  30. 30.
    A. Michaelis, Justus Liebigs Ann. Chem., 339, 117 (1905).Google Scholar
  31. 31.
    A. Michaelis and A. Schäfer, Justus Liebigs Ann. Chem., 397, 119 (1913).Google Scholar
  32. 32.
    E. v. Meyer, P. Berge, R. Oehler, and E. Schletter, J. Prakt. Chem., 90, 1 (1914).Google Scholar
  33. 33.
    K. H. Saunders, The Aromatic Diazo-Compounds and their Technical Applications, Edward Arnold & Co., London (1949), 443 p.Google Scholar
  34. 34.
    R. Elderfield (editor), Heterocyclic Compounds [Russian translation, Yu. K. Yur'ev (editor)], Vol. 5, Izd-vo Inostr. Lit., Moscow (1954), p. 104.Google Scholar
  35. 35.
    A. Ganesan and C. H. Heathcock, J. Org. Chem., 58, 6155 (1993).Google Scholar
  36. 36.
    C. B. Vicentini, M. Manfrini, M. Mazzanti, A. Scatturin, C. Romagnoli, and D. Mares, Arch. Pharm., 332, 337 (1999).Google Scholar
  37. 37.
    Е. Mohr, J. Prakt. Chem., 79, 1 (1909).Google Scholar
  38. 38.
    Е. Mohr, J. Prakt. Chem., 90, 223 (1914).Google Scholar
  39. 39.
    M. V. Gorelik, S. P. Titova, and V. I. Ribinov, Zh. Org. Khim., 16, 1322 (1980).Google Scholar
  40. 40.
    M. V. Gorelik and V. I. Lomzakova, Zh. Org. Khim., 22, 1054 (1986).Google Scholar
  41. 41.
    G. F. Duffin and J. D. Kendall, J. Chem. Soc., 408 (1954).Google Scholar
  42. 42.
    G. Pieri, E. Rosati, R. Battisti, and G. Burei, US Pat. Appl. 4268436.Google Scholar
  43. 43.
    M. A. Weaver and C. A. Coates, US Pat. Appl. 4459229.Google Scholar
  44. 44.
    J. R. Beck, R. P. Gajewski, M. P. Lynch, and F. L. Wright, J. Heterocycl. Chem., 24, 267 (1987).Google Scholar
  45. 45.
    E. M. Kandeel, V. B. Baghos, I. S. Mohareb, and M. H. Elnagdi, Arch. Pharm, 316, 713 (1983).Google Scholar
  46. 46.
    D. G. Farnum and P. Yates, Chem. Ind., 42, 659 (1960).Google Scholar
  47. 47.
    D. G. Farnum and P. Yates, J. Am. Chem. Soc., 84, 1399 (1962).Google Scholar
  48. 48.
    W. L. Magee, C. B. Rao, J. Glinka, H. Hui, T. J. Amick, D. Fiscus, S. Kakodkar, M. Nair, and H. Shechter, J. Org. Chem., 52, 5538 (1987).Google Scholar
  49. 49.
    M. H. Elnagdi, M. R. H. Elmoghayar, S. M. Fahmy, M. K. A. Ibraheim, and H. H. Alnim, Z. Naturforsch., 33b, 216 (1978).Google Scholar
  50. 50.
    K. L. Kirk and L. A. Cohen, J. Am. Chem. Soc., 95, 4619 (1973).Google Scholar
  51. 51.
    H. Lund, J. Chem. Soc., 686 (1933).Google Scholar
  52. 52.
    C. Musante, Gazz. Chim. Ital., 75, 109 (1945).Google Scholar
  53. 53.
    H. Reimlinger and A. van Overstraeten, Chem. Ber., 99, 3350 (1966).Google Scholar
  54. 54.
    F. Fabra, E. Fos, and J. Vilarrasa, Tetrahedron Lett., 20, 3179 (1979).Google Scholar
  55. 55.
    F. Fabra, J. Vilarrasa, and J. Coll, J. Heterocycl. Chem., 15, 1447 (1978).Google Scholar
  56. 56.
    W. E. Parham and I. M. Aldre, J. Org. Chem., 25, 1259 (1960).Google Scholar
  57. 57.
    E. Alcalde, J. M. Garcia-Marquina, and J. De Mendoza, An. Quim., 70, 959 (1974).Google Scholar
  58. 58.
    A. Echevarria and J. Elguero, Synth. Commun., 23, 925 (1993).Google Scholar
  59. 59.
    J. F. Chiarello and D. Rugg, US Pat. Appl. 20040122075 A1.Google Scholar
  60. 60.
    V. P. Perevalov, L. I. Baryshnenkova, E. A. Denisova, M. A. Andreeva, and B. I. Stepanov, Chem. Heterocycl. Compd., 20, 1397 (1984). [Khim. Geterotsikl. Soedin., 1691 (1984).]Google Scholar
  61. 61.
    S. A. Shevelev and I. L. Dalinger, Zh. Org. Khim., 34, 1127 (1998).Google Scholar
  62. 62.
    C. C. Cheng, J. Heterocycl. Chem., 5, 195 (1968).Google Scholar
  63. 63.
    L. I. Bagal, M. S. Pevzner, A. N. Frolov, and N. I. Sheludyakova, Chem. Heterocycl. Compd., 6, 240 (1970). [Khim. Geterotsikl. Soedin., 259 (1970).]Google Scholar
  64. 64.
    N. V. Latypov, V. A. Silevich, P. A. Ivanov, and M. S. Pevzner, Chem. Heterocycl. Compd., 12, 1355 (1976). [Khim. Geterotsikl. Soedin., 12, 1649 (1976).]Google Scholar
  65. 65.
    P. A. S. Smith and H. Dounchis, J. Org. Chem., 38, 2958 (1973).Google Scholar
  66. 66.
    D. Clarke, R. W. Mares and H. McNab, J. Chem. Soc., Perkin Trans. 1, 1799 (1997).Google Scholar
  67. 67.
    R. Bellemin and D. Festal, J. Heterocycl. Chem., 21, 1017 (1984).Google Scholar
  68. 68.
    S. Yamamoto, T. Sato, Y. Iwasawa, F. Suzuki, T. Ikai, K. Suzuki, and T. Nawamaki, J. Pesticide Sci., 15, 531 (1990).Google Scholar
  69. 69.
    B. Kumar, R. Soni, J. Z. Patel, S. Jha, S. A. Shedage, N. Gandhi, K. V. Sairam, V. Pawar, N. Sadhwani, P. Mitra, M. R. Jain, and P. R. Patel, Bioorg. Med. Chem. Lett., 18, 3882 (2008).Google Scholar
  70. 70.
    M. K. Spassova and R. D. Zakharieva, Collect. Czech. Chem. Commun., 54, 196 (1989).Google Scholar
  71. 71.
    S. Yamamoto, K. Morimoto, and T. Sato, J. Heterocycl. Chem., 28, 1545 (1991).Google Scholar
  72. 72.
    T. Nishiwaki, F. Fujiyama, and E. Minamisono, J. Chem. Soc., Perkin Trans. 1, 1871 (1974).Google Scholar
  73. 73.
    R. B. Toche, M. A. Kazi, and M. N. Jachak, Org. Prep. Proced. Int., 40, 551 (2008).Google Scholar
  74. 74.
    N. Kornblum, in: A. Ya. Berlin (editor), Organic Reactions [Russian translation], Vol. 2, Izd-vo Inostr. Lit., Moscow (1950), p. 285.Google Scholar
  75. 75.
    K. Kirschke, in: D. Klamann and E. Schaumann (editors), Houben-Weyl. Methoden der organischen chemie, Georg Thieme Verlag, Stuttgart (1994), p. 399.Google Scholar
  76. 76.
    X. L. Ren, H. B. Li, Ch. Wu, and H. Z. Yang, ARKIVOC, xv, 59 (2005).Google Scholar
  77. 77.
    J. De Mendoza and J. M. Garcia-Marquina, An. Quim., 66, 911 (1970).Google Scholar
  78. 78.
    E. Jucker, A. J. Lindenmann, and A. Vogel, US Pat. Appl. 3299091.Google Scholar
  79. 79.
    G. Ege, K. Gilbert, and R. Heck, Chem. Ber., 117, 1726 (1984).Google Scholar
  80. 80.
    M. A. Khan and A. C. C. Freitas, J. Heterocycl. Chem., 20, 277 (1983).Google Scholar
  81. 81.
    M. Taniguchi and T. Sato, US Pat. Appl. 5110941.Google Scholar
  82. 82.
    Y. F. Shealy and C. A. O'Dell, J. Pharm. Sci., 60, 554 (1971).Google Scholar
  83. 83.
    G. Ege, K. Gilbert, and R. Heck, Angew. Chem., Int. Ed. Engl., 21, 698 (1982).Google Scholar
  84. 84.
    G. Daidone, D. Raffa, B. Maggio, M. V. Raimondi, F. Plescia, and D. Schillaci, Eur. J. Med. Chem., 39, 219 (2004).Google Scholar
  85. 85.
    C. W. Noell and C. C. Cheng, J. Med. Chem., 14, 1245 (1971).Google Scholar
  86. 86.
    E. A. Al-Agamey and M. R. H. Elmoghayar, An. Quim., Ser. C, 81, 14 (1985).Google Scholar
  87. 87.
    J. Schawartz, M. Hornyak, E. Majorszki, A. David, and G. Horvath, US Pat. Appl. 4049639.Google Scholar
  88. 88.
    L. V. Shmelev, E. P. Anpenova, and G. V. Avramenko, Zh. Org. Khim., 29, 601 (1993).Google Scholar
  89. 89.
    G. V. Avramenko, Z. V. Bezuglaya, E. P. Anpenova, and E. V. Zhilina, Izv. Vuzov. Khimiya i Khim. Tekhnologiya, 36, 43 (1993).Google Scholar
  90. 90.
    M. W. Partridge and M. F. G. Stevens, J. Chem. Soc. C, 1127 (1966).Google Scholar
  91. 91.
    V. M. Dziomko and B. K. Berestevich, Chem. Heterocycl. Compd., 14, 313 (1978). [Khim. Geterotsikl. Soedin., 382 (1978).]Google Scholar
  92. 92.
    A. M. S. Youssef, R. A. M. Faty, and M. M. Youssef, J. Korean Chem. Soc., 45, 448 (2001).Google Scholar
  93. 93.
    V. M. Dziomko and B. K. Berestevich, Chem. Heterocycl. Compd., 15, 657 (1979). [Khim. Geterotsikl. Soedin., 805 (1978).]Google Scholar
  94. 94.
    F. Benguerel and R. Mislin, US Pat. Appl. 4685934.Google Scholar
  95. 95.
    U. Dreyer and R. Gross, US Pat. Appl. 3133051.Google Scholar
  96. 96.
    M. W. Partridge and M. F. G. Stevens, J. Chem. Soc. C, 1828 (1967).Google Scholar
  97. 97.
    E. B. Towne, W. H. Moore, and J. B. Dickey, US Pat. Appl. 3336285.Google Scholar
  98. 98.
    D. D. Chapman, US Pat. Appl. 5144015.Google Scholar
  99. 99.
    H. S. El-Kashef, K. U. Sadek, and M. H. Elnagdi, J. Chem. Eng. Data, 27, 103 (1982).Google Scholar
  100. 100.
    S. M. Fahmy, M. El-Hosami, S. El-Gamal, and M. H. Elnagdi, J. Chem. Technol. Biotechnol., 32, 1042 (1982).Google Scholar
  101. 101.
    A. Deeb, M. El-Mobayed, A. E. N. Essawy, and A. Abd El Hamid, Collect. Czech. Chem. Commun., 55, 2790 (1990).Google Scholar
  102. 102.
    F. Karci, Color. Technol., 121, 275 (2005).Google Scholar
  103. 103.
    F. Karci and F. Karci, Dyes Pigm., 76, 147 (2008).Google Scholar
  104. 104.
    E. A.-A. Hafez, E. M. Zayed, and K. U. Sadek, J. Heterocycl. Chem., 22, 241 (1985).Google Scholar
  105. 105.
    E. M. Zayed, A. A. A. Elbannany, and S. A. S. Ghozlan, Pharmazie, 40, 194 (1985).Google Scholar
  106. 106.
    A. A. A. Elbannany, L. I. Ibrahiem, and S. A. S. Ghozlan, Pharmazie, 43, 128 (1988).Google Scholar
  107. 107.
    M. A. Weaver and L. Shuttleworth, Dyes Pigm., 3, 81 (1982).Google Scholar
  108. 108.
    N. A. Hamdy, H. A. Abdel-Aziz, A. M. Farag, and I. M. I. Fakhr, Monatsh. Chem., 138, 1001 (2007).Google Scholar
  109. 109.
    M. A. Radwan, E. A. Ragab, N. M. Sabry, and S. M. El-Shenawy, Bioorg. Med. Chem., 15, 3832 (2007).Google Scholar
  110. 110.
    Y. Kurasawa, H. S. Kim, K. Yonekura, A. Takada, and Y. Okamoto, J. Heterocycl. Chem., 26, 857 (1989).Google Scholar
  111. 111.
    K. V. Vatsuro and G. L. Mishchenko, Named Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976).Google Scholar
  112. 112.
    Y. Ahmad and P. A. S. Smith, J. Org. Chem., 36, 2972 (1971).Google Scholar
  113. 113.
    K. M. Dawood, A. M. Farag, and N. A. Khedr, ARKIVOC, xv, 166 (2008).Google Scholar
  114. 114.
    S. L. Bogza, V. I. Dulenko, S. Yu. Zinchenko, K. I. Kobrakov, and I. V. Pavlov, Chem. Heterocycl. Compd., 40, 1506 (2004). [Khim. Geterotsikl. Soedin., 1738 (2004).]Google Scholar
  115. 115.
    S. Bogza and S. Zinchenko, Visn. Lviv Un-tu. Seriya Khim., 49, 3 (2008).Google Scholar
  116. 116.
    V. V. Didenko, V. A. Voronkova, and Kh. S. Shikhaliev, Russ. J. Org. Chem., 45, 211 (2009). [Zh. Org. Khim., 45, 223 (2009).]Google Scholar
  117. 117.
    E. V. Tretyakov, D. W. Knight, and S. F. Vasilevsky, J. Chem. Soc., Perkin Trans. 1, 3721 (1999).Google Scholar
  118. 118.
    S. F. Vasilevsky and E. V. Tretyakov, Liebigs Ann., 1995, 775 (1995).Google Scholar
  119. 119.
    R. Justoni and R. Fusco, Gazz. Chim. Ital., 68, 59 (1938).Google Scholar
  120. 120.
    C. C. Cheng, R. K. Robins, K. C. Cheng, and D. C. Lin, J. Pharm. Sci., 57, 1044 (1968).Google Scholar
  121. 121.
    S. Bondock, R. Rabie, H. A. Etman, and A. A. Fadda, Eur. J. Med. Chem., 43, 2122 (2008).Google Scholar
  122. 122.
    A. M. K. El-Dean and A. A. Geies, J. Chem. Res., Synop., 352 (1997).Google Scholar
  123. 123.
    F. Seela, M. Lindner, V. Glaçon, and W. Lin, J. Org. Chem., 69, 4695 (2004).Google Scholar
  124. 124.
    J. A. Montgomery and H. J. Thomas, J. Med. Chem., 15, 182 (1972).Google Scholar
  125. 125.
    F. M. A. El-Taweel, Alexandria J. Pharm. Sci., 12, 11 (1998).Google Scholar
  126. 126.
    B. Yang, Y. Lu, C.-J. Chen, J.-P. Cui, and M.-S. Cai, Dyes Pigm., 83, 144 (2009).Google Scholar
  127. 127.
    G. R. Bedford, M. W. Partridge, and M. F. G. Stevens, J. Chem. Soc. C, 1214 (1966).Google Scholar
  128. 128.
    J. Slouka, J. Kubata and V. Bekarek, Acta Univ. Palack. Olomuc.: Fac. Rerum Natur., 49, 219 (1976).Google Scholar
  129. 129.
    A. G. A. Elagamey, F. M. A. El-Taweel, and F. A. Amer, Collect. Czech. Chem. Commun., 51, 2193 (1986).Google Scholar
  130. 130.
    T. Novinson, T. Okabe, R. K. Robins, and T. R. Matthews, J. Med. Chem., 19, 517 (1976).Google Scholar
  131. 131.
    M. H. Elnagdi, E. M. Zayed, M. A. E. Khalifa, and S. A. Ghozlan, Monatsh. Chem., 112, 245 (1981).Google Scholar
  132. 132.
    A. O. Abdelhamid, H. F. Zohdi, and G. S. Mohamed, Heteroat. Chem., 10, 508 (1999).Google Scholar
  133. 133.
    E. V. Shchegolkov, Y. V. Burgart, O. G. Khudina, V. I. Saloutin, and O. N. Chupakhin, Russ. Chem. Rev., 79, 31 (2010). [Usp. Khim., 79, 33 (2010).]Google Scholar
  134. 134.
    M. Kočevar, D. Kolman, H. Krajnc, S. Polanc, B. Porovne, B. Stanovnik, and M. Tišler, Tetrahedron, 32, 725 (1976).Google Scholar
  135. 135.
    V. V. Didenko, I. V. Ledenyova, and Kh. S. Shikhaliev, Vestn. VGU. Ser. Khim. Biol. Farm., No. 1, 7 (2010).Google Scholar
  136. 136.
    O. G. Khudina, E. V. Shchegol'kov, Ya. V. Burgart, M. I. Kodess, O. N. Kazheva, A. N. Chekhlov, G. V. Shilov, O. A. Dyachenko, V. I. Saloutin, and O. N. Chupakhin, J. Fluorine Chem., 126, 1230 (2005).Google Scholar
  137. 137.
    M. R. Shaaban, J. Fluorine Chem., 129, 1156 (2008).Google Scholar
  138. 138.
    A. Z. A. Hassanien, S. A. S. Ghozlan, and M. H. Elnagdi, J. Chinese Chem. Soc., 51, 575 (2004).Google Scholar
  139. 139.
    A. G. A. Elagamey, F. A. El Taweel, F. A. Amer, and H. H. Zoorob, Arch. Pharm., 320, 246 (1987).Google Scholar
  140. 140.
    V. V. Didenko, Kh. S. Shikhaliev, and I. V. Ledenyova, Chem. Heterocycl. Compd., 45, 248 (2009). [Khim. Geterotsikl. Soedin., 307 (2009).]Google Scholar
  141. 141.
    E. M. Zayed, S. A. S. Ghozlan, and A.-A. H. Ibrahim, Monatsh. Chem., 115, 431 (1984).Google Scholar
  142. 142.
    M. A. Raslan, R. M. Abd El-Aal, M. E. Hassan, N. A. Ahamed, and K. U. Sadek, J. Chinese Chem. Soc., 48, 91 (2001).Google Scholar
  143. 143.
    M. H. Elnagdi, M. R. H. Elmoghayer, H. A. Elfaham, M. M. Sallam, and H. H. Alnima, J. Heterocycl. Chem., 17, 209 (1980).Google Scholar
  144. 144.
    M. A. Barsy, E. A. Elrady, Μ. E. Hassan, and F. M. Abd El Latif, Heterocycl. Commun., 6, 545 (2000).Google Scholar
  145. 145.
    K. U. Sadek, M. A. Selim, M. H. Elnagdi, and H. H. Otto, Bull. Chem. Soc. Jpn., 66, 2927 (1993).Google Scholar
  146. 146.
    C. Almansa, A. F. de Arriba, F. L. Cavalcanti, L. A. Gómez, A. Miralles, M. Merlos, J. García-Rafanell, and J. Forn, J. Med. Chem., 44, 350 (2001).Google Scholar
  147. 147.
    A. O. Abdelhamid, V. B. Baghos, and M. M. A. Halim, J. Chem. Res., Synop., 31, 420 (2007).Google Scholar
  148. 148.
    D. M. Berger, M. D. Dutia, D. W. Hopper, and N. Torres, WO Pat. Appl. 2009039387.Google Scholar
  149. 149.
    M. Azimioara, C. Cow, R. Epple, G. Lelais, J. Mecom, and V. Nikulin, US Pat. Appl. 8575168.Google Scholar
  150. 150.
    E. J. Gray, M. F. G. Stevens, G. Tennant, and R. J. S. Vevers, J. Chem. Soc., Perkin Trans. 1, No. 14, 1496 (1976).Google Scholar
  151. 151.
    O. A. Fathalla and M. E. A. Zaki, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 37B, 484 (1998).Google Scholar
  152. 152.
    M. H. Elnagdi, N. H. Taha, F. A. M. Abd El All, R. M. Abdel-Motaleb, and F. F. Mahmoud, Collect. Czech. Chem. Commun., 54, 1082 (1989).Google Scholar
  153. 153.
    M. M. Girges, M. A. Hanna, and A. A. Fadda, Chem. Pap., 47, 186 (1993).Google Scholar
  154. 154.
    M. R. H. Elmoghayar, M. K. A. Ibrahim, I. El-Sakka, A. H. H. Elghandour, and M. H. Elnagdi, Arch. Pharm., 316, 697 (1983).Google Scholar
  155. 155.
    F. Karcı, İ. Şener, A. Demirçalı, and N. Burukoğlu, Color. Technol., 122, 264 (2006).Google Scholar
  156. 156.
    M. R. H. Elmoghayar, S. O. Abdalla, and M. Y. A.-S. Nasr, J. Heterocycl. Chem., 21, 781 (1984).Google Scholar
  157. 157.
    A. G. A. Elagamey, Arch. Pharmacal Res., 10, 173 (1987).Google Scholar
  158. 158.
    J. Slouka and V. Bekarek, Collect. Czech. Chem. Commun., 49, 275 (1984).Google Scholar
  159. 159.
    A. M. Farag, Z. E. Kandeel, and M. H. Elnagdi, J. Chem. Res., Synop., 10 (1994).Google Scholar
  160. 160.
    S. M. Hassan, M. M. Abdel Aal, A. A. El-Maghraby, and M. S. Bashandy, Phosphorus, Sulfur Silicon Relat. Elem., 184, 427 (2009).Google Scholar
  161. 161.
    P. Cankar and J. Slouka, J. Heterocycl. Chem., 40, 71 (2003).Google Scholar
  162. 162.
    E. N. Ulomskii, S. L. Deev, V. L. Rusinov, and O. N. Chupakhin, Zh. Org. Khim., 35, 1384 (1999).Google Scholar
  163. 163.
    M. A. E. Khalifa, E. M. Zayed, M. H. Mohamed, and M. H. Elnagdi, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 22B, 552 (1983).Google Scholar
  164. 164.
    M. M. M. Ramiz, A. H. H. Elgandour, and A.-G. A. Elagamey, J. Prakt. Chem., 330, 641 (1988).Google Scholar
  165. 165.
    M. M. Abdelall, Phosphorus, Sulfur Silicon Relat. Elem., 184, 2208 (2009).Google Scholar
  166. 166.
    I. V. Ledenyova, V. V. Didenko, V. V. Dotsenko, and K. S. Shikhaliev, Tetrahedron Lett., 55, 1239 (2014).Google Scholar
  167. 167.
    A. M. Farag, K. M. Dawood, and H. A. Abdel-Aziz, J. Chem. Res., 808 (2004).Google Scholar
  168. 168.
    A. M. Farag, K. M. Dawood, and Z. E. Kandeel, Tetrahedron, 52, 7893 (1996).Google Scholar
  169. 169.
    M. A. Berghot and E. B. Moawad, Eur. J. Pharm. Sci., 20, 173 (2003).Google Scholar
  170. 170.
    S. M. Sayed, M. A. Raslan, M. A. Khalil, and K. M. Dawood, Heteroat. Chem., 10, 385 (1999).Google Scholar
  171. 171.
    M. M. A. Khalik, J. Chem. Res., Synop., 21, 198 (1997).Google Scholar
  172. 172.
    N. M. Abed, N. S. Ibrahim, S. M. Fahmy, and M. H. Elnagdi, Org. Prep. Proced. Int., 17, 107 (1985).Google Scholar
  173. 173.
    V. L. Rusinov and O. N. Chupakhin, Ros. Khim. Zh., 41 (2), 103 (1997).Google Scholar
  174. 174.
    V. L. Rusinov, E. N. Ulomskii, O. N. Chupakhin, M. M. Zubairov, A. B. Kapustin, N. I. Mitin, M. I. Zhiravetskii, and I. A. Vinograd, Pharm. Chem. J., 24, 646 (1990). [Khim. Farm. Zh., 24, № 9, 41 (1990).]Google Scholar
  175. 175.
    V. L. Rusinov, T. L. Pilicheva, O. N. Chupakhin, N. A. Klyuev, and D. T. Allakhverdieva, Chem. Heterocycl. Compd., 22, 543 (1986). [Khim. Geterotsikl. Soedin., 662 (1986).]Google Scholar
  176. 176.
    M. A. Al-Shiekh, A. M. S. El-Din, E. A. Hafez, and M. H. Elnagdi, J. Chem. Res., 174 (2004).Google Scholar
  177. 177.
    H. A. Abdel-Aziz, N. A. Hamdy, I. M. I. Fakhr, and A. M. Farag, J. Heterocycl. Chem., 45, 1033 (2008).Google Scholar
  178. 178.
    M. R. Shaaban, T. S. Saleh, and A. M. Farag, Heterocycles, 78, 699 (2009).Google Scholar
  179. 179.
    A. O. Abdelhamid, A. A. Fahmi, and K. N. M. Halim, Synth. Commun., 43, 1101 (2013).Google Scholar
  180. 180.
    A. O. Abdelhamid, A. A. Fahmi, and A. A. M. Alsheflo, Eur. J. Chem., 3, 129 (2012).Google Scholar
  181. 181.
    M. A. Mohamed, J. Heterocycl. Chem., 47, 517 (2010).Google Scholar
  182. 182.
    K. M. Dawood, Heteroat. Chem., 15, 432 (2004).Google Scholar
  183. 183.
    A. O. Abdelhamid and A. S. Shawali, Z. Naturforsch., B: J. Chem. Sci., 42, 613 (1987).Google Scholar
  184. 184.
    H. Reimlinger and R. Merenyi, Chem. Ber., 103, 3284 (1970).Google Scholar
  185. 185.
    S. Al-Mousawi, E. John, M. M. Abdelkhalik, and M. H. Elnagdi, J. Heterocycl. Chem., 40, 689 (2003).Google Scholar
  186. 186.
    T. A. Farghaly and M. M. Abdalla, Bioorg. Med. Chem. Lett., 17, 8012 (2009).Google Scholar
  187. 187.
    H. M. Hassaneen, N. M. Abunada, and H. M. Hassaneen, Nat. Sci., 2, 1349 (2010).Google Scholar
  188. 188.
    Kh. S. Shikhaliev, V. V. Didenko, V. A. Voronkova, and D. V. Kryl'skii, Russ. Chem. Bull., Int. Ed., 58, 1034 (2009). [Izv. Akad. Nauk, Ser. Khim., 58, 1008 (2009).]Google Scholar
  189. 189.
    R. A. M. Faty and A. M. S. Youssef, Curr. Org. Chem., 13, 1577 (2009). J. Farras, E. Fos, R. Ramos, and J. Vilarrasa, J. Org. Chem., 53, 887 (1988).Google Scholar
  190. 190.
    I. V. Ledenyova, V. V. Didenko, and Kh. S. Shikhaliev, Butler. Soobsch., 17 (5), 24 (2009).Google Scholar
  191. 191.
    I. V. Ledenyova, V. V. Didenko, A. S. Shestakov, and Kh. S. Shikhaliev, J. Heterocycl. Chem., 50, 573 (2013).Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • I. V. Ledenyova
    • 1
    Email author
  • V. V. Didenko
    • 1
  • Kh. S. Shikhaliev
    • 1
  1. 1.Voronezh State UniversityVoronezhRussia

Personalised recommendations