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Multicomponent interphase synthesis of heterocyclic compounds (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

This review covers studies on the synthesis of heterocyclic compounds using multicomponent reactions in aqueous emulsions and suspensions, as well as on the surface of natural clays and silica gel. A comparative analysis was carried out of the efficiency of this approach for obtaining various classes of heterocyclic compounds. Mechanisms for increasing the rate of multicomponent reactions were also examined.

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References

  1. J. Zhu and H. Bienayme (editors), Multicomponent Reactions, Wiley-VCH, Weinheim, Germany (2005).

    Google Scholar 

  2. A. Dömling, Chem. Rev., 106, 17 (2006).

    Article  Google Scholar 

  3. D. J. Ramon and M. Yus, Angew. Chem., Int. Ed., 44, 1602 (2005).

    Article  CAS  Google Scholar 

  4. R. V. A. Orru and M. de Greef, Synthesis, 1471 (2003).

  5. J. Zhu, Eur. J. Org. Chem., 1133 (2003).

  6. N. Isambert and R. Lavilla, Chem. Eur. J., 14, 8444 (2008).

    Article  CAS  Google Scholar 

  7. C. Hulme and Y.-S. Lee, Mol. Diversity, 12, 1 (2008).

    Article  CAS  Google Scholar 

  8. A. V. Lygin and A. de Meijere, Angew. Chem., Int. Ed., 49, 9094 (2010).

    Article  CAS  Google Scholar 

  9. S. Sadjadi and M. M. Heravi, Tetrahedron, 67, 2707 (2011).

    Article  CAS  Google Scholar 

  10. B. B. Toure and D. G. Hall, Chem. Rev., 109, 4439 (2009).

    Article  CAS  Google Scholar 

  11. J. E. Biggs-Houck, A. Younai, and J. T. Shaw, Curr. Opin. Chem. Biol., 14, 371 (2010).

    Article  CAS  Google Scholar 

  12. M. A. Kolosov, V. D. Orlov, D. A. Beloborodov, and V. V. Dotsenko, Mol. Diversity, 13, 5 (2009).

    Article  CAS  Google Scholar 

  13. M. A. Mironov, QSAR Comb. Sci., 25, 423 (2006).

    Article  CAS  Google Scholar 

  14. B. Ganem, Acc. Chem. Res., 42, 463 (2009).

    Article  CAS  Google Scholar 

  15. A. Dömling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000).

    Article  Google Scholar 

  16. U. M. Lindstrom (editor), Organic Reactions in Water: Principles, Strategies and Applications, Blackwell, Oxford (2007).

  17. A. Chanda and V. V. Fokin, Chem. Rev., 109, 725 (2009).

    Article  CAS  Google Scholar 

  18. R. N. Butler and A. G. Coyne, Chem. Rev., 110, 6302 (2010).

    Article  CAS  Google Scholar 

  19. C.-J. Li and T.-H. Chan, Comprehensive Organic Reactions in Aqueous Media, 2nd ed., Wiley-VCH, Weinheim, Germany (2007).

    Book  Google Scholar 

  20. C. H. Zhou, Appl. Clay Sci., 53, 87 (2011).

    Article  CAS  Google Scholar 

  21. C. D. Rideout and R. Breslow, J. Am. Chem. Soc., 102, 7816 (1980).

    Article  CAS  Google Scholar 

  22. P. A. Grieco, K. Yoshida, and P. Garner, J. Org. Chem., 48, 3137 (1983).

    Article  CAS  Google Scholar 

  23. R. Breslow, Acc. Chem. Res., 37, 471 (2004).

    Article  CAS  Google Scholar 

  24. S. Otto and J. B. F. N. Engberts, Org. Biomol. Chem., 1, 2809 (2003).

    Article  CAS  Google Scholar 

  25. M. C. Pirrung and K. Das Sarma, J. Am. Chem. Soc., 126, 444 (2004).

    Article  CAS  Google Scholar 

  26. Y. Jung and R. A. Marcus, J. Am. Chem. Soc., 129, 5492 (2007).

    Article  CAS  Google Scholar 

  27. M. C. Pirrung, K. Das Sharma, and J. Wang, J. Org. Chem., 73, 8723 (2008).

    Article  CAS  Google Scholar 

  28. S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, and K. B. Sharpless, Angew. Chem., Int. Ed., 44, 3275 (2005).

    Article  CAS  Google Scholar 

  29. S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 107, 1768 (1975).

    Article  Google Scholar 

  30. I.-H. Chen, J.-N. Young, and S. J. Yu, Tetrahedron, 60, 11903 (2004).

    Article  CAS  Google Scholar 

  31. C. Loncaric, K. Manabe, and S. Kobayashi, Adv. Synth. Catal., 345, 475 (2003).

    Article  CAS  Google Scholar 

  32. Y. Gu, R. De Sousa, G. Frapper, C. Bachmann, J. Barrault, and F. Jerome, Green Chem., 11, 1968 (2009).

    Article  CAS  Google Scholar 

  33. M. A. Mironov, M. N. Ivantsova, and V. S. Mokrushin, Mol. Diversity, 6, 193 (2003).

    Article  CAS  Google Scholar 

  34. M. A. Mironov, M. N. Ivantsova, M. I. Tokareva, and V. S. Mokrushin, Tetrahedron Lett., 46, 3957 (2005).

    Article  CAS  Google Scholar 

  35. A. R. Extance, D. W. M. Benzies, and J. J. Morrish, QSAR Comb. Sci., 25, 484 (2006).

    Article  CAS  Google Scholar 

  36. M. C. Pirrung and K. Das Sharma, Synlett, 1425 (2004).

  37. I. Kanizsai, S. Gyonfalvi, Z. Szakonyi, R. Sillanpaa, and F. Fulop, Green Chem., 9, 357 (2007).

    Article  CAS  Google Scholar 

  38. M. Adib, M. Mahdavi, S. Bagherzadeh, L.-G. Zhu, and M. Rahimi-Nasrabadi, Tetrahedron Lett., 51, 27 (2010).

    Article  CAS  Google Scholar 

  39. A. Shaabani, M. B. Teimouri, and H. R. Bijanzadeh, Tetrahedron Lett., 43, 9151 (2002).

    Article  CAS  Google Scholar 

  40. A. N. Kolontsova, M. N. Ivantsova, M. I. Tokareva, and M. A. Mironov, Mol. Diversity, 14, 543 (2010).

    Article  CAS  Google Scholar 

  41. N. A. Petasis and I. A. Zavialov, J. Am. Chem. Soc., 119, 445 (1997).

    Article  CAS  Google Scholar 

  42. N. R. Candeias, P. M. S. D. Cal, V. Andre, M. T. Duarte, L. F. Veiros, and P. M. P. Gois, Tetrahedron, 66, 2736 (2010).

    Article  CAS  Google Scholar 

  43. G. Vasuki and K. Kumaravel, Tetrahedron Lett., 49, 5636 (2008).

    Article  CAS  Google Scholar 

  44. M. Babaie and H. Sheibani, Arabian J. Chem., 4, 159 (2011).

    Article  CAS  Google Scholar 

  45. G. Shanthi and P. T. Perumal, Tetrahedron Lett., 48, 6785 (2007).

    Article  CAS  Google Scholar 

  46. B. Yan and Y. Liu, Org. Lett., 9, 4323 (2007).

    Article  CAS  Google Scholar 

  47. D. Dallinger and C. O. Kappe, Chem. Rev., 107, 2563 (2007).

    Article  CAS  Google Scholar 

  48. S. J. Tu, Y. Zhang, J. Jiang, B. Jiang, J.-Y. Zhang, R.-H. Jia, and F. Shi, Eur. J. Org. Chem., 1522 (2007).

  49. J. B. F. N. Engberts and M. J. Blandamer, Chem. Commun., 1701 (2001).

  50. J. B. F. N. Engberts, Pure Appl. Chem., 64, 1653 (1992).

    Article  CAS  Google Scholar 

  51. P. A. Grieco, P. Garner, and Z.-M. He, Tetrahedron Lett., 24, 1897 (1983).

    Article  CAS  Google Scholar 

  52. I. Carranco, J. L. Diaz, O. Jimenez, M. Vendrell, F. Albericio, M. Royo, and R. Lavilla, J. Comb. Chem., 7, 33 (2005).

    Article  CAS  Google Scholar 

  53. K. Manabe, Y. Mori, T. Wakabayashi, S. Nagayama, and S. Kobayashi, J. Am. Chem. Soc., 122, 7202 (2000).

    Article  CAS  Google Scholar 

  54. S. Otto, J. B. F. N. Engberts, and J. C. T. Kwak, J. Am. Chem. Soc., 120, 9517 (1998).

    Article  CAS  Google Scholar 

  55. K. Manabe, Y. Mori, and S. Kobayashi, Tetrahedron, 57, 2537 (2001).

    Article  CAS  Google Scholar 

  56. C. S. McKay, D. C. Kennedy, and J. P. Pezacki, Tetrahedron Lett., 50, 1893 (2009).

    Article  CAS  Google Scholar 

  57. R. Ballini, G. Bosica, M. L. Conforti, R. Maggi, A. Mazzacani, P. Righi, and G. Sartori, Tetrahedron, 57, 1395 (2001).

    Article  CAS  Google Scholar 

  58. P. A. Grieco and A. Bahsas, Tetrahedron Lett., 29, 5855 (1988).

    Article  CAS  Google Scholar 

  59. A. Ouach, S. Gmouh, M. Pucheault, and M. Vaultier, Tetrahedron, 64, 1962 (2008).

    Article  CAS  Google Scholar 

  60. R. S. Varma, Tetrahedron, 58, 1235 (2002).

    Article  CAS  Google Scholar 

  61. G. Sartori, F. Bigi, R. Maggi, A. Mazzacani, and G. Oppici, Eur. J. Org. Chem., 13, 2513 (2001).

    Article  Google Scholar 

  62. S. K. Guchhait, K. Jadeja, and C. Madaan, Tetrahedron Lett., 50, 6861 (2009).

    Article  CAS  Google Scholar 

  63. A. Kulkarni and B. Torok, Green Chem., 12, 875 (2010).

    Article  CAS  Google Scholar 

  64. J. S. Biradar and B. Sharanbasappa, Green Chem. Lett. Rev., 2, 237 (2009).

    Article  CAS  Google Scholar 

  65. M. A. Chari, Tetrahedron Lett., 52, 6108 (2011).

    Article  Google Scholar 

  66. S. R. Kolla and Y. R. Lee, Tetrahedron, 66, 8938 (2010).

    Article  CAS  Google Scholar 

  67. R. S. Varma, Pure Appl. Chem., 73, 193 (2001).

    Article  CAS  Google Scholar 

  68. V. K. Rai, S. Singh, P. Singh, and L. D. S. Yadav, Synthesis, 4051 (2010).

  69. I. Devi and P. J. Bhuyan, Synlett, 283 (2010).

  70. F. Bigi, S. Carloni, B. Frullanti, R. Maggi, and G. Sartori, Tetrahedron Lett., 40, 3465 (1999).

    Article  CAS  Google Scholar 

  71. L. D. S. Yadav, C. Awasthi, V. K. Rai, and A. Rai, Tetrahedron Lett., 48, 4899 (2007).

    Article  CAS  Google Scholar 

  72. L. D. S. Yadav and A. Rai, Carbohydr. Res., 344, 2329 (2009).

    Article  CAS  Google Scholar 

  73. S. S. Pandit, S. K. Bhalerao, U. S. Aher, G. L. Adhav, and V. U. Pandit, J. Chem. Sci., 123, 421 (2011).

    Article  CAS  Google Scholar 

  74. M. Dabiri, M. Baghbanzadeh, M. S. Nikcheh, and E. Arzroomchilar, Bioorg. Med. Chem. Lett., 18, 436 (2008).

    Article  CAS  Google Scholar 

  75. R. Maggi, R. Ballini, G. Sartori, and R. Sartorio, Tetrahedron Lett., 45, 2297 (2004).

    Article  CAS  Google Scholar 

  76. K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda, J. Am. Chem. Soc., 127, 9674 (2005).

    Article  CAS  Google Scholar 

  77. A. Dandia, G. Sharma, R. Singh, and A. Laxkar, ARKIVOC, xiv, 100 (2009).

  78. A. Ramazani, A. T. Mahyari, M. Rouhani, and A. Rezaei, Tetrahedron Lett., 50, 5625 (2009).

    Article  CAS  Google Scholar 

  79. S. Banerjee, A. Horn, H. Khatri, and G. Sereda, Tetrahedron Lett., 52, 1878 (2011).

    Article  CAS  Google Scholar 

  80. H. R. Shaterian, H. Yarahmadi, and M. Ghashang, Tetrahedron Lett., 52, 1263 (2009).

    Google Scholar 

  81. M. Maheswara, V. Siddaiah, Y. K. Rao, Y.-M. Tzeng, and C. Sridhar, J. Mol. Catal. A: Chem., 260, 179 (2006).

    Article  CAS  Google Scholar 

  82. S. Balalaie and A. Arabanian, Green Chem., 2, 274 (2000).

    Article  CAS  Google Scholar 

  83. B. Sadeghi, B. B. F. Mirjalili, and M. M. Hashemi, Tetrahedron Lett., 49, 2575 (2008).

    Article  CAS  Google Scholar 

  84. S. Kantevari, S. V. N. Vuppalapati, D. O. Biradar, and L. Nagarapu, J. Mol. Catal. A: Chem., 266, 109 (2007).

    Article  CAS  Google Scholar 

  85. A. R. Karimi, Z. Alimohammadi, and M. M. Amini, Mol. Diversity, 14, 635 (2010).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Ural Federal University named after First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    M. N. Ivantsova, M. I. Tokareva & M. A. Mironov

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  1. M. N. Ivantsova
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  2. M. I. Tokareva
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  3. M. A. Mironov
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Correspondence to M. A. Mironov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 626-645, April, 2012.

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Ivantsova, M.N., Tokareva, M.I. & Mironov, M.A. Multicomponent interphase synthesis of heterocyclic compounds (Review). Chem Heterocycl Comp 48, 584–600 (2012). https://doi.org/10.1007/s10593-012-1031-1

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