Skip to main content
SpringerLink
Log in

Multicomponent heterocyclization reactions with controlled selectivity (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The review is devoted to the problem of controlling the selectivity of multicomponent heterocyclizations. Special attention has been paid to analysis of the literature of the last decade concerning the use of nonclassical methods of activating chemical processes, such as microwave and ultrasonic irradiation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. S. L. Schreiber, Science, 287, 1964 (2000).

    Article  CAS  Google Scholar 

  2. B. M. Trost, Acc. Chem. Res., 35, 695 (2002).

    Article  CAS  Google Scholar 

  3. P. A. Wender, G. G. Gamber, R. D. Hubbard, S. M. Pham, and L. Zhang, J. Am. Chem. Soc., 127, 2836 (2005).

    Article  CAS  Google Scholar 

  4. P. A. Wender, S. T. Handy, and D. L. Wright, Chem. Ind., 765 (1997).

  5. E. Ruijter, R. Scheffelaar, and R. V. A. Orru, Ang. Chem., Int. Ed., 50, 6234 (2011).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  7. F. Sha and X. Huang, Angew. Chem., Int. Ed., 48, 3458 (2009).

    Article  CAS  Google Scholar 

  8. Y. Suzuki, Y. Ohta, S. Oishi, N. Fujii, and H. Ohno, J. Org. Chem., 74, 4246 (2009).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  10. A. Kruithof, E. Ruijter, and R. V. A. Orru, Curr. Org. Chem., 15, 204 (2011).

    Article  CAS  Google Scholar 

  11. V. A. Chebanov, K. A. Gura, and S. M. Desenko, Top. Heterocycl. Chem., 23, 41 (2010).

    Article  CAS  Google Scholar 

  12. S. M. Desenko, V. D. Orlov, N. V. Getmanskii, O. V. Shishkin, S. V. Lindeman, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 481 (1993). [Chem. Heterocycl. Compd., 29, 406 (1993)].

  13. K. Wermann and M. Hartmann, Synthesis, 189 (1991).

  14. A. T. Khan and M. M. Khan, Tetrahedron Lett., 52, 3455 (2011).

    Article  CAS  Google Scholar 

  15. I. Drizin, M. W. Holladay, L. Yi, H. Q. Zhang, S. Gopalakrishnan, M. Gopalakrishnan, K. L. Whiteaker, S. A. Buckner, J. P. Sullivan, and W. A. Carroll, Bioorg. Med. Chem. Lett., 12, 1481 (2002).

    Article  CAS  Google Scholar 

  16. V. A. Chebanov, V. E. Saraev, S. M. Desenko, V. N. Chernenko, I. V. Knyazeva, U. Groth, T. N. Glasnov, and C. O. Kappe, J. Org. Chem., 73, 5110 (2008).

    Article  CAS  Google Scholar 

  17. V. A. Chebanov, Ya. I. Sakhno, S. M. Desenko, S. V. Shishkina, V. I. Musatov, O. V. Shishkin, and I. V. Knyazeva, Synthesis, 2597 (2005).

  18. Q. Chen, L.-L. Jiang, C.-N. Chen, and G.-F. Yang, J. Heterocycl. Chem., 46, 139 (2009).

    Article  CAS  Google Scholar 

  19. M. P. Sibi and M. Liu, Curr. Org. Chem., 5, 719 (2001).

    Article  CAS  Google Scholar 

  20. S. P. Flanagan and P. J. Guiry, J. Organomet. Chem., 691, 2125 (2006).

    Article  CAS  Google Scholar 

  21. G. Zanoni, F. Castronovo, M. Franzini, G. Vidari, and E. Giannini, Chem. Soc. Rev., 32, 115 (2003).

    Article  CAS  Google Scholar 

  22. D. Bonne, Y. Coquerel, T. Constantieux, and J. Rodriguez, Tetrahedron: Asymmetry, 21, 1085 (2010).

    Article  CAS  Google Scholar 

  23. G. Guillena, D. J. Ramón, and M. Yus, Tetrahedron: Asymmetry, 18, 693 (2007).

    Article  CAS  Google Scholar 

  24. A.-N. Alba, X. Companyo, M. Viciano, and R. Rios, Curr. Org. Chem., 13, 1432 (2009).

    Article  CAS  Google Scholar 

  25. R. Wohlgemuth, Curr. Opin. Biotechnol., 21, 713 (2010).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  27. D. M. D’Souza and T. J. J. Müller, Chem. Soc. Rev., 36, 1095 (2007).

    Article  Google Scholar 

  28. N. Isambert, M. del Mar Sanchez Duque, J.-C. Plaquevent, Y. Génisson, J. Rodriguez, and T. Constantieux, Chem. Soc. Rev., 40, 1347 (2011).

    Article  CAS  Google Scholar 

  29. J. B. Bariwal, J. C. Trivedi, and E. V. van der Eycken, Top. Heterocycl. Chem., 25, 169 (2010).

    Article  CAS  Google Scholar 

  30. S. Caddick and R. Fitzmaurice, Tetrahedron, 65, 3325 (2009).

    Article  CAS  Google Scholar 

  31. M. C. Bagley and M. Caterina Lubinu, Top. Heterocycl. Chem., 1, 31 (2006).

    Article  CAS  Google Scholar 

  32. C. O. Kappe, Angew. Chem. Int. Ed., 43, 6250 (2004).

    Article  CAS  Google Scholar 

  33. W. Bonrath and R. Schmidt, in: Advances in Organic Synthesis, Science, Bentham (2005), p. 81.

  34. R. Cella and H. A. Stefani, Tetrahedron, 65, 2619 (2009).

    Article  CAS  Google Scholar 

  35. V. V. Lipson, V. D. Orlov, S. M. Desenko, T. M. Karnozhitskaya, and M. G. Shirobokova, Khim. Geterotsikl. Soedin., 664 (1999). [Chem. Heterocycl. Compd., 35, 595 (1999)].

  36. V. V. Lipson, V. V. Borodina, and M. G. Shirobokova, Ukr. Khim. Zh., 71, 95 (2005).

    CAS  Google Scholar 

  37. V. V. Lipson, S. M. Desenko, V. V. Borodina, M. G. Shirobokova, T. M. Karnozhitskaya, V. I. Musatov, and S. V. Kravchenko, Khim. Geterotsikl. Soedin., 246, (2005). [Chem. Heterocycl. Compd., 41, 216 (2005)].

  38. V. V. Lipson, V. V. Borodina, and V. I. Musatov, Zh. Org. Farm. Khim., 4, No. 1, 62 (2006).

    CAS  Google Scholar 

  39. V. V. Lipson, V. D. Orlov, S. M. Desenko, S. V. Shishkina, O. V. Shishkin, and M. G. Shirobokova, Khim. Geterotsikl. Soedin., 1190 (2000). [Chem. Heterocycl. Compd., 36, 1039 (2000)].

    Google Scholar 

  40. V. V. Lipson, S. M. Desenko, M. G. Shirobokova, O. V. Shishkin, and S. V. Shishkina, Zh. Org. Khim., 42, 1040 (2006).

    Google Scholar 

  41. S. Tu., C. Li, F. Shi, D. Zhou, Q. Shao, L. Cao, and B. Jiang, Synthesis, 369 (2008).

  42. S.-L. Wang, Y.-P. Liu, B.-H. Xu, X.-H. Wang, B. Liang, and S.-J. Tu, Tetrahedron, 67, 9417 (2011).

    Article  CAS  Google Scholar 

  43. S. M. Desenko, V. D. Orlov, N. V. Getmanskii, O. V. Shishkin, S. V. Lindeman, and Yu. T. Struchkov, Dokl. Akad. Nauk SSSR, 324, 801 (1992).

    CAS  Google Scholar 

  44. S. Tu, B. Jiang, Y. Zhang, R. Jia, J. Zhang, C. Yao, and F. Shi, Org. Biomol. Chem., 5, 355 (2007).

    Article  CAS  Google Scholar 

  45. D. Tejedor and F. Garcia-Tellado, Chem. Soc. Rev., 36, 484 (2007).

    Article  CAS  Google Scholar 

  46. N. Elders, E. Ruijter, F. J. J. de Kanter, M. B. Groen, and R. V. A. Orru, Chem.–Eur. J., 14, 4961 (2008).

    Article  CAS  Google Scholar 

  47. F. A. Carey and R. J. Sundberg, in: Advanced Organic Chemistry. Part A: Structure and Mechanisms, Springer, New York (2007), p. 285.

  48. A. Loupy (editor), Microwaves in Organic Synthesis, 2nd ed., Wiley, Weinheim (2006).

  49. A. de la Hoz, A. Díaz-Ortiz, and A. Moreno, Curr. Org. Chem., 8, 903 (2004).

    Article  Google Scholar 

  50. A. de la Hoz, M. P. Prieto, M. Rajzmann, A. de Cózar, A. Díaz-Ortiz, A. Moreno, and F. P. Cossío, Tetrahedron, 64, 8169 (2008).

    Article  Google Scholar 

  51. T. Razzaq, J. M. Kremsner, and C. O. Kappe, J. Org. Chem., 73, 6321 (2008).

    Article  CAS  Google Scholar 

  52. M. A. Herrero, J. M. Kremsner, and C. O. Kappe, J. Org. Chem., 73, 36 (2008).

    Article  CAS  Google Scholar 

  53. V. A. Chebanov, E. A. Muravyova, S. M. Desenko, V. I. Musatov, I. V. Knyazeva, S. V. Shishkina, O. V. Shishkin, and C. O. Kappe, J. Comb. Chem., 8, 427 (2006).

    Article  CAS  Google Scholar 

  54. E. A. Muravyova, S. M. Desenko, R. V. Rudenko, S. V. Shishkina, O. V. Shishkin, Yu. V. Sen'ko, E. V. Vashchenko, and V. A. Chebanov, Tetrahedron, 67, 9389 (2011).

    Article  CAS  Google Scholar 

  55. V. A. Chebanov, Ya. I. Sakhno, S. M. Desenko, V. N. Chernenko, V. I. Musatov, S. V. Shishkina, O. V. Shishkin, and C. O. Kappe, Tetrahedron, 63, 1229 (2007).

    Article  CAS  Google Scholar 

  56. Ya. I. Sakhno, S. M. Desenko, S. V. Shishkina, O. V. Shishkin, D. O. Sysoyev, U. Groth, C. O. Kappe, and V. A. Chebanov, Tetrahedron, 64, 11041 (2008).

    Article  CAS  Google Scholar 

  57. Ya. I. Sakhno, S. V. Shishkina, O. V. Shishkin, M. I. Musatov, E. V. Vashchenko, S. M, Desenko, and V. A. Chebanov, Mol. Diversity, 14, 523 (2010).

    Article  CAS  Google Scholar 

  58. Ya. I. Sakhno, S. M. Desenko, S. V. Shishkina, O. V. Shishkin, V. I. Musatov, and V. A. Chebanov, Synthesis, 1120 (2011).

  59. V. A. Chebanov, Ya. I. Sakhno, and S. M. Desenko, Ultrason. Sonochem., 19, 707 (2012).

    Article  CAS  Google Scholar 

  60. N. Yu. Gorobets, Yu. V. Sedash, K. S. Ostras, O. V. Zaremba, S. V. Shishkina, V. N. Baumer, O. V. Shishkin, S. M. Kovalenko, S. M. Desenko, and E. V. van der Eycken, Tetrahedron Lett., 51, 2095 (2010).

    Article  CAS  Google Scholar 

  61. J. Světlik and V. Kettmann, Tetrahedron Lett., 52, 1062 (2011).

    Article  Google Scholar 

  62. V. A. Chebanov, V. E. Saraev, S. M. Desenko, V. N. Chernenko, S. V. Shishkina, O. V. Shishkin, K. M. Kobzar, and C. O. Kappe, Org. Lett., 9, 1691 (2007).

    Article  CAS  Google Scholar 

  63. A. Yu. Andriushchenko, S. M. Desenko, V. N. Chernenko, and V. A. Chebanov, J. Heterocycl. Chem., 48, 365 (2011).

    Article  CAS  Google Scholar 

  64. V. Chebanov and S. Desenko, Multicomponent heterocyclizations with controlled selectivity. Reactions of carbonyl compounds with nitrogen-containing mono- bi-, and polynucleophiles. LAP LAMBERT Academic Publishing, Saarbrücken (2011).

  65. E. A. Muravyova, S. V. Shishkina, V. I. Musatov, I. V. Knyazeva, O. V. Shishkin, S. M. Desenko, and V. A. Chebanov, Synthesis, 1375 (2009).

  66. H.-G. Cheng, C.-B. Chen, F. Tan, N.-J. Chang, J.-R. Chen, and W.-J. Xiao, Eur. J. Org. Chem., 4976 (2010).

  67. J. Sun, L.-L. Zhang, E.-Y. Xia, and C.-G. Yan, J. Org. Chem., 74, 3398 (2009).

    Article  CAS  Google Scholar 

  68. S.-J. Tu, X.-D. Cao, W.-J. Hao, X.-H. Zhang, S. Yan, S,-S. Wu, Z.-G. Han, and F. Shi, Org. Biomol. Chem., 7, 557 (2009).

    Article  CAS  Google Scholar 

  69. E. S. Gladkov, V. A. Chebanov, S. M. Desenko, O. V. Shishkin, S. V. Shishkina, D. Dallinger, and C. O. Kappe, Heterocycles, 73, 469 (2007).

    Article  CAS  Google Scholar 

  70. R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, Acc. Chem. Res., 29, 123 (1996).

    Article  CAS  Google Scholar 

  71. S. M. Desenko, V. D. Orlov, and X. Estrada, Khim. Geterotsikl. Soedin., 999 (1990). [Chem. Heterocycl. Compd., 26, 839 (1990)].

    Google Scholar 

  72. V. M. Chernyshev, D. A. Khoroshkin, A. N. Sokolov, V. A. Taranushich, E. S. Gladkov, S. V. Shishkina, O. V. Shishkin, and S. M. Desenko, J. Heterocycl. Chem., 45, 1419 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Scientific-Technological Complex “Institute of Monocrystals”, National Academy of Sciences of Ukraine, 60 Lenin Ave., Kharkiv, 61001, Ukraine

    V. A. Chebanov

Authors
  1. V. A. Chebanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. M. Desenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Chebanov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 607-625, April, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chebanov, V.A., Desenko, S.M. Multicomponent heterocyclization reactions with controlled selectivity (Review). Chem Heterocycl Comp 48, 566–583 (2012). https://doi.org/10.1007/s10593-012-1030-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1030-2

Keywords

Search

Navigation