Advertisement

Review Journal of Chemistry

, Volume 4, Issue 3, pp 221–251 | Cite as

Sonochemistry: Synthesis of bioactive heterocycles

  • Essam M. Hussein
  • Khalid S. Khairou
Article

Abstract

In the recent years, being dedicated on green chemistry using environmentally benign reagents and conditions is one of the most fascinating developments in synthesis of widely used organic compounds. This review describes the theory and importance of ultrasound as an efficient tool in the synthesis of heterocyclic compounds.

Keywords

ultrasound ultrasonic irradiation bioactive heterocycles sonochemical sonochemistry 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Eicher, T. and Hauptmann, S., The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Aapplications, Weinheim: Wiley, 2003, 2nd ed.Google Scholar
  2. 2.
    Mason, T.J. and Lorimer, J.P., Applied Sonochemistry: Uses of Power Ultrasound in Chemistry and Processing, Weinheim: Wiley, 2002.Google Scholar
  3. 3.
    Li, J.T., Li, Y.W., Song, Y.L., and Chen, G.F., Ultrason. Sonochem., 2012, vol. 19, p. 1.Google Scholar
  4. 4.
    Ghahremanzadeh, R., Fereshtehnejad, F., Mirzaei, P., and Bazgir, A., Ultrason. Sonochem., 2011, vol. 18, p. 415.Google Scholar
  5. 5.
    Kowsari, E. and Mallakmohammadi, M., Ultrason. Sonochem., 2011, vol. 18, p. 447.Google Scholar
  6. 6.
    He, J.Y., Xin, H.X., Yan, H., Song, X.Q., and Zhong, R.G., Ultrason. Sonochem., 2011, vol. 18, p. 466.Google Scholar
  7. 7.
    Li, J.T., Yin, Y., and Sun, M.X., Ultrason. Sonochem., 2010, vol. 17, p. 363.Google Scholar
  8. 8.
    Bazgir, A., Ahadi, S., Ghahremanzadeh, R., Khavasi, H.R., and Mirzaei, P., Ultrason. Sonochem., 2010, vol. 17, p. 447.Google Scholar
  9. 9.
    Suslick, K.S., Science, 1990, vol. 247, p. 1439.Google Scholar
  10. 10.
    Fillion, H. and Luche, J.-L., Synthetic Organic Sonochemistry, Luche, J.-L., Ed., New York: Plenum, 1998.Google Scholar
  11. 11.
    Gedanken, A., Ultrason. Sonochem., 2004, vol. 11, p. 47.Google Scholar
  12. 12.
    Rechards, W.T. and Loomis, A.L., J. Am. Chem. Soc., 1927, vol. 49, p. 3086.Google Scholar
  13. 13.
    Porter, C.W. and Young, L., J. Am. Chem. Soc., 1938, vol. 60, p. 1497.Google Scholar
  14. 14.
    Renaud, P., Bull. Soc. Chim. Fr., 1950, p. 1044.Google Scholar
  15. 15.
    Sehgal, C.M. and Wang, S.Y.J., J. Am. Chem. Soc., 1981, vol. 103, p. 6606.Google Scholar
  16. 16.
    Cella, R. and Stefani, H.A., Tetrahedron, 2009, vol. 65, p. 2619.Google Scholar
  17. 17.
    Singh, V., Kaur, K.P., Khurana, A., and Kad, G.L., Resonance, 1998, vol. 9, p. 56.Google Scholar
  18. 18.
    Hata, Y., Watanabe, M., Matasubara, T., and Touchi, A., J. Am. Chem. Soc., 1976, vol. 98, p. 6033.Google Scholar
  19. 19.
    Schirmeister, T. and Peric, M., Bioorg. Med. Chem., 2000, vol. 8, p. 1281.Google Scholar
  20. 20.
    Harada, K.I., Tomita, K., Fujii, K., Masuda, K., Mikami, Y., Yazawa, K., and Komaki, H., J. Antibiot., 2004, vol. 57, p. 125.Google Scholar
  21. 21.
    Miller, T.W., Tristram, E.W., and Wolf, F.J., J. Antibiot., 1971, vol. 24, p. 48.Google Scholar
  22. 22.
    Ogasawara, Y. and Liu, H-W., J. Am. Chem. Soc., 2009, vol. 131, p. 18066.Google Scholar
  23. 23.
    Tsuchida, T., Inuma, H., Kinoshita, N., Ikeda, T., Sawa, T., Hamada, M., and Takenchi, T., J. Antibiot., 1995, vol. 48, p. 217.Google Scholar
  24. 24.
    Chanda, B.M., Vyas, R., and Bedekar, A.V., J. Org. Chem., 2001, vol. 66, p. 30.Google Scholar
  25. 25.
    Konev, A.S., Novikov, M.S., and Khlebnikov, A.F., Tetrahedron Lett., 2005, vol. 46, p. 8337.Google Scholar
  26. 26.
    Coldham, I. and Hufton, R., Chem. Rev., 2005, vol. 105, p. 2765.Google Scholar
  27. 27.
    Eftekhari-Sis, B. and Vahdati-Khajeh, S., Curr. Chem. Lett., 2013, vol. 2, no. 2, p. 85.Google Scholar
  28. 28.
    Mamaghani, M. and Dastmard, S., ARKIVOC, 2009, no. 2, p. 168.Google Scholar
  29. 29.
    Lin, Z. and Li, J., E-J. Chem., 2012, vol. 9, p. 267.Google Scholar
  30. 30.
    Pizzuti, L., Piovesan, L.A., Flores, A.F.C., Quina, F.H., and Pereira, C.M.P., Ultrason. Sonochem., 2009, vol. 16, p. 728.Google Scholar
  31. 31.
    Pizzuti, L., Martins, P.L.G., Ribeiro, B.A., Quina, F.H., Pinto, E., Flores, A.F.C., Venzke, D., and Pereira, C.M.P., Ultrason. Sonochem., 2010, vol. 17, p. 34.Google Scholar
  32. 32.
    Pathak, V.N., Joshi, R., Sharma, J., Gupta, N., and Rao, V.M., Phosphorus, Sulfur Silicon Relat. Elem., 2009, vol. 184, p. 1854.Google Scholar
  33. 33.
    EL-Rahman, N.M., Saleh, T.S., and Mady, M.F., Ultrason. Sonochem., 2009, vol. 16, p. 70.Google Scholar
  34. 34.
    Li, J.-T., Yin, Y., Li, L., and Sun, M.-X., Ultrason. Sonochem., 2010, vol. 17, p. 11.Google Scholar
  35. 35.
    Gomha, S.M. and Khalil, K.D., Molecules, 2012, vol. 17, p. 9335.Google Scholar
  36. 36.
    Chimenti, F., Bolasco, A., Secci, D., Chimenti, P., Granese, A., Carradori, S., Yanez, M., Orallo, F., Ortuso, F., and Alcaro, S., Bioorg. Med. Chem., 2010, vol. 18, p. 5715.Google Scholar
  37. 37.
    Nabid, M.R., Rezaei, S.J.T., Ghahremanzadeh, R., and Bazgir, A., Ultrason. Sonochem., 2010, vol. 17, p. 159.Google Scholar
  38. 38.
    Al-Mutairi, A.A., El-Baih, F.E.M., and Al-Hazimi, H.M., J. Saudi Chem. Soc., 2010, vol. 14, p. 287.Google Scholar
  39. 39.
    Zou, Y., Wu, H., Hu, Y., Liu, H., Zhao, X., Ji, H., and Shi, D., Ultrason. Sonochem., 2011, vol. 18, p. 708.Google Scholar
  40. 40.
    Darandale, S.N., Sangshetti, J.N., and Shinde, D.B., J. Korean Chem. Soc., 2012, vol. 56, p. 328.Google Scholar
  41. 41.
    Shekouhy, M. and Hasaninejad, A., Ultrason. Sonochem., 2012, vol. 19, p. 307.Google Scholar
  42. 42.
    Khosropour, A.R., Ultrason. Sonochem., 2008, vol. 15, p. 659.Google Scholar
  43. 43.
    Shelke, K.F., Sapkal, S.B., Sonar, S.S., Madje, B.R., Shingate, B.B., and Shingare, M.S., Bull. Korean. Chem. Soc., 2009, vol. 30, p. 1057.Google Scholar
  44. 44.
    Joshi, R.S., Mandhane, P.G., Dabhade, S.K., and Gill, C.H., J. Chin. Chem. Soc., 2010, vol. 57, p. 1227.Google Scholar
  45. 45.
    Arani, N.M. and Safari, V.J., Ultrason. Sonochem., 2011, vol. 18, p. 640.Google Scholar
  46. 46.
    Singh, B.S., Lobo, H.R., Pinjari, D.V., Jarag, K.J., Pandit, A.B., and Shankarling, G.S., Ultrason. Sonochem., 2013, vol. 20, p. 287.Google Scholar
  47. 47.
    Toukoniitty, B., Toukoniitty, E., Maki-Arvela, P., Mikkola, J.-P., Salmi, T., Murzim, D., Yu, P., and Kooyman, J., Ultrason. Sonochem., 2006, vol. 13, p. 68.Google Scholar
  48. 48.
    Entezari, M.H., Asghari, A., and Hadizadeh, F., Ultrason. Sonochem., 2008, vol. 15, p. 119.Google Scholar
  49. 49.
    Mamaghani, M., Loghmanifar, A., and Taati, M.R., Ultrason. Sonochem., 2011, vol. 18, p. 45.Google Scholar
  50. 50.
    Neuenfeldt, P.D., Duval, A.R., Drawanz, B.B., Rosales, P.F., Gomes, C.R.B., Pereira, C.M.P., and Cunico, W., Ultrason. Sonochem., 2011, vol. 18, p. 65.Google Scholar
  51. 51.
    Sibor, J. and Pazdera, P., Molecules, 1996, vol. 1, p. 157.Google Scholar
  52. 52.
    Matsuda, T. and Hirao, I., Nippon Kagaku Zasshi, 1965, vol. 86, p. 1195.Google Scholar
  53. 53.
    Hurst, E.W. and Hull, R.I., J. Med. Pharm. Chem., 1961, vol. 3, p. 215.Google Scholar
  54. 54.
    Bokaeva, S.S. and Kaz, Nauch-Issled, Tr. Kaz. Nauchno-Issled. Inst. Onkol. Radiol., 1967, vol. 3, p. 305.Google Scholar
  55. 55.
    Kato, T., JP Patent 59,190,974, 1984.Google Scholar
  56. 56.
    Sadanandam, Y.S., Shetty, M.M., and Diwan, P.V., Eur. J. Med. Chem., 1992, vol. 27, p. 87.Google Scholar
  57. 57.
    Looper, K., PCT Int. Appl., Pfizer, WO 11, 1990.Google Scholar
  58. 58.
    Kurono, M., Hayashi, M., Miura, K., Isogawa, Y., Sawai, K., JP Patent 62, 267, 272, 1987.Google Scholar
  59. 59.
    Zhidovinova, M.S., Fedorova, O.V., Rusinov, G.L., and Ovchinnikova, I.G., Russ. Chem. Bull., 2003, vol. 52, p. 2527.Google Scholar
  60. 60.
    Biginelli, P., Gazz. Chim. Ital., 1893, vol. 23, p. 360.Google Scholar
  61. 61.
    Li, J.-T., Han, J.-F., Yang, J.-H., and Li, T.-S., Ultrason. Sonochem., 2003, vol. 10, p. 119.Google Scholar
  62. 62.
    Yadav, J.S., Subba Reddy, B.V., Bhaskar Reddy, K., Raj, K.S., and Prasad, A.R., J. Chem. Soc., Perkin Trans. 1, 2001, vol. 1, p. 1939.Google Scholar
  63. 63.
    Stefani, H.A., Oliveira, C.B., Almeida, R.B., Pereira, C.M.P., Braga, R.C., Cella, R., Borges, V.C., Savegnago, L., and Nogueira, C.W., Eur. J. Med. Chem., 2006, vol. 41, p. 513.Google Scholar
  64. 64.
    Li, J.-T., Lin, Z.-P., Han, J.-F., and Li, T.-S., Synth. Commun., 2004, vol. 34, p. 2623.Google Scholar
  65. 65.
    Liu, C-J. and Wang, Ji-D., Molecules, 2010, vol. 15, p. 2087.Google Scholar
  66. 66.
    Safaei-Ghomi, J. and Ghasemzadeh, M.A., J. Serb. Chem. Soc., 2011, vol. 76, p. 679.Google Scholar
  67. 67.
    Niralwad, K.S., Shingate, B.B., and Shingare, M.S., J. Chin. Chem. Soc., 2010, vol. 57, p. 89.Google Scholar
  68. 68.
    Murata, T., Shimada, M., Sakakibara, S., Yoshino, T., Kadono, H., Masuda, T., Shimazaki, M., Shintani, T., Fuchikami, K., Sakai, K., Inbe, H., Takeshita, K., Niki, T., Umeda, M., Bacon, K.B., Ziegelbauer, K.B., and Lowinger, T.B., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 913.Google Scholar
  69. 69.
    Mantri, M., De Graaf, O., Van Veldhoven, J., Goblyos, A., Von Frijtag, Drabbe., Kunzel, J.K., MulderKrieger, T., Link, R., De Vries, H., Beukers, M.W., Brussee, J., and Ijzerman, A.P., J. Med. Chem., 2008, vol. 51, p. 4449.Google Scholar
  70. 70.
    Deng, J., Sanchez, T., Al-Mawsawi, L.Q., Dayam, R., Yunes, R.A., Garofalo, A., Bolger, M.B., and Neamati, N., Bioorg. Med. Chem., 2007, vol. 15, p. 4985.Google Scholar
  71. 71.
    Ruiz, E., Rodriguez, H., Coro, J., Salfran, E., Suarez, M., Martinez-Alvarez, R., and Martin, N., Ultrason. Sonochem., 2011, vol. 18, p. 32.Google Scholar
  72. 72.
    Safari, J., Banitaba, S.H., and Khalili, S.D., Ultrason. Sonochem., 2012, vol. 19, p. 1061.Google Scholar
  73. 73.
    Betti, L., Floridi, M., Giannacini, G., Manetti, F., Strappaghetti, G., Tafi, A., and Botta, M., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 171.Google Scholar
  74. 74.
    Sotelo, E., Fraiz, N., Yanez, M., Terrades, V., Laguna, R., Cano, E., and Ravina, E., Bioorg. Med. Chem., 2002, vol. 10, p. 2873.Google Scholar
  75. 75.
    Sotelo, E., Fraiz, N., Yanez, M., Laguna, R., Cano, E., and Ravina, E., Bioorg. Med. Chem. Lett., 2002, vol. 27, p. 1574.Google Scholar
  76. 76.
    Van Der May, M., Hatzelmann, A., Van Der Laan, I.J., Sterk, G.J., Thibaut, V., and Timmerman, H., J. Med. Chem., 2001, vol. 44, p. 2511.Google Scholar
  77. 77.
    Van der Mey, M., Boss, H., Couwenberg, D., Hatzelmann, A., Sterk, G.J., Goubitz, K., Schenk, H., and Timmerman, H., J. Med. Chem., 2002, vol. 45, p. 2526.Google Scholar
  78. 78.
    Van Der May, M., Bommele, K.M., Boss, H., Hatzelmann, A., Van Slingerland, M., Sterk, G.J., and Timmerman, H., J. Med. Chem., 2003, vol. 46, p. 2008.Google Scholar
  79. 79.
    Betti, L., Zanelli, M., Giannacini, G., Manetti, F., Schenone, S., and Strappaghetti, G., Bioorg. Med. Chem. Lett., 2006, vol. 14, p. 2828.Google Scholar
  80. 80.
    Demirayak, S., Karaburun, A.C., Kayagil, I., Erol, K., and Sirmagul, B., Arch. Pharm. Res., 2004, vol. 27, p. 13.Google Scholar
  81. 81.
    Yamaguchi, M., Kamei, K., Koga, T., Akima, M., Kuroki, T., and Ohi, N., J. Med. Chem., 1993, vol. 36, p. 4052.Google Scholar
  82. 82.
    Black, L.A., Basha, A., Kolasa, T., Kort, M.E., and Liu, H., MacCarty, C.M., Patel, M.V., Oohde, J.J., Coghlan, M.J., and Stewart, A.O., Int. Appl. Chem. Abstr., 2000, vol. 132, p. 321867.Google Scholar
  83. 83.
    Ishida, A., Homma, K., Kono, H., Tamura, K., and Sasaki, Y., Chem. Abstr., 1994, vol. 121, 35618.Google Scholar
  84. 84.
    Pinna, G.A., Curzu, M.M., Loriga, M., Cignarella, G., Barlocco, D., and Malandrino, S., Farmaco-Ed. Sci., 1985, vol. 40, p. 979.Google Scholar
  85. 85.
    Zare, L., Mahmoodi, N.O., Yahyazadeh, A., and Nikpassand, M., Ultrason. Sonochem., 2012, vol. 19, p. 740.Google Scholar
  86. 86.
    Sudha, S. and Pasha, M.A., Ultrason. Sonochem., 2012, vol. 19, p. 994.Google Scholar
  87. 87.
    Banitaba, S.H., Safari, J., and Khalili, S.D., Ultrason. Sonochem., 2013, vol. 20, p. 401.Google Scholar
  88. 88.
    Gangjee, A., Adair, O., and Queener, S.F., J. Med. Chem., 1999, vol. 42, p. 2447.Google Scholar
  89. 89.
    Grivsky, E.M., Lee, S., Sigel, C.W., Duch, D.S., and Nichol, C.A., J. Med. Chem., 1980, vol. 23, p. 327.Google Scholar
  90. 90.
    Heber, D., Heers, C., and Ravens, U., Pharmazie, 1993, vol. 48, p. 537.Google Scholar
  91. 91.
    Furuya, S. and Ohtaki, T., Eur. Pat. Appl. EP 608565, Chem. Abstr., 1994, vol. 121, 205395w.Google Scholar
  92. 92.
    Sakuma, Y., Hasegawa, M., Kataoka, K., Hoshina, K., Yamazaki, N., Kadota, T., and Yamaguchi, H., PCT Int., 91 05,785, 1989.Google Scholar
  93. 93.
    Singh, G., Singh, G., Yadav, A.K., and Mishraa, K., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 2002, vol. 41, no. 2, p. 430.Google Scholar
  94. 94.
    Zakharov, A.V., Gavrilov, M.Y., Demina, L.M., Novoselova, G.N., Gornova, N.A., and Konshin, M.Y., Khim. Farm. Zh., 1994, vol. 28, p. 24.Google Scholar
  95. 95.
    DeGraw, J.I., Christie, P.H., Clowell, W.T., and Sirotnak, F.M., J. Med. Chem., 1992, vol. 35, p. 320.Google Scholar
  96. 96.
    Hussein, E.M., Z. Naturforsch., B: J. Chem. Sci., 2012, vol. 67, p. 231.Google Scholar
  97. 97.
    Ablajan, K., Kamil, W., Tuoheti, A., and Wan-Fu, S., Molecules, 2012, vol. 17, p. 1860.Google Scholar
  98. 98.
    Saleh, T.S., Eldebss, T.M.A., and Albishri, H.M., Ultrason. Sonochem., 2012, vol. 19, p. 49.Google Scholar
  99. 99.
    Cordell, G.A., The Alkaloids: Chemistry and Biology, San Diego: Academic, 1998.Google Scholar
  100. 100.
    Okita, T. and Isobe, M., Tetrahedron, 1994, vol. 50, p. 11143.Google Scholar
  101. 101.
    Kornet, M.J. and Thio, A.P., J. Med. Chem., 1976, vol. 19, p. 892.Google Scholar
  102. 102.
    Skiles, J.W. and McNeil, D., Tetrahedron Lett., 1990, vol. 31, p. 7277.Google Scholar
  103. 103.
    Padmavathi, V., Ramana Reddy, T.V., and Audisesha Reddy, K., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 2007, vol. 46, p. 818.Google Scholar
  104. 104.
    Li, J.-T., Zhai, X.-L., and Chen, G.-F., Ultrason. Sonochem., 2010, vol. 17, p. 356.Google Scholar
  105. 105.
    Dandia, A., Singh, R., Bhaskaran, S., and Samant, S.D., Green Chem., 2011, vol. 13, p. 1852.Google Scholar
  106. 106.
    Jadidi, K., Gharemanzadeh, R., Mehrdad, M., Darabi, H.R., Khavasi, H.R., and Asgari, D., Ultrason. Sonochem., 2008, vol. 15, p. 124.Google Scholar
  107. 107.
    Rezaei, S.J.T., Nabid, M.R., Yari, A., and Weng, N.S., Ultrason. Sonochem., 2011, vol. 18, p. 49.Google Scholar
  108. 108.
    Hua, Y., Zou, Y., Wub, H., and Shi, D., Ultrason. Sonochem., 2012, vol. 19, p. 264.Google Scholar
  109. 109.
    Dandia, A., Singh, R., and Bhaskaran, S., Ultrason. Sonochem., 2011, vol. 18, p. 1113.Google Scholar
  110. 110.
    Dandia, A., Singh, R., and Bhaskaran, S., Ultrason. Sonochem., 2010, vol. 17, p. 399.Google Scholar
  111. 111.
    Bazgir, A., Ahadi, S., Ghahremanzadeh, R., Khavasi, H.R., and Mirzaei, P., Ultrason. Sonochem., 2010, vol. 17, p. 447.Google Scholar
  112. 112.
    Wang, J., Bai, X., Xu, C., Wang, Y., Lin, W., Zou, Y., and Shi, D., Molecules, 2012, vol. 17, p. 8674.Google Scholar
  113. 113.
    Rezaei, S.J.T., Bide, Y., and Nabid, M.R., Tetrahedron Lett., 2012, vol. 53, p. 5123.Google Scholar
  114. 114.
    Hussein, E.M., Monatsh. Chem., 2012, vol. 144, p. 1691.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceAssiut UniversityAssiutEgypt
  2. 2.Department of Chemistry, Faculty of Applied SciencesUmm Al-Qura UniversityMakkahSaudi Arabia

Personalised recommendations