DOI QR코드

DOI QR Code

Convenient One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with HMDS in the Presence of Molecular Iodine

  • Received : 2011.10.24
  • Accepted : 2012.01.07
  • Published : 2012.04.20

Abstract

A one-pot efficient procedure for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in the presence of molecular iodine has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, and the availability of reagents.

Keywords

References

  1. Grimmett, M. R. Comprehensive Heterocyclic Chemistry, Vol. 5; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; p 345.
  2. Grimmett, M. R. Comprehensive Heterocyclic Chemistry II, Vol. 3; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; p 77-220.
  3. The Pharmacological Basis of Therapeutics, 10th ed.; Gilman, A. G., Goodman, L. S., Eds.; Macmillan: New York, 2001.
  4. Prisinano, T.; Law, H.; Dukat, M.; Slassi, A.; MaClean, N.; Demchyshyn, L.; Glennon, R. A. Bioorg. Med. Chem. 2001, 9, 613. https://doi.org/10.1016/S0968-0896(00)00275-3
  5. Jones, R. C. F.; Nichols, J. R. Tetrahedron Lett. 1990, 31, 1771. https://doi.org/10.1016/S0040-4039(00)88877-2
  6. Langlois, Y.; Dalko, P. I. J. Org. Chem. 1998, 63, 8107. https://doi.org/10.1021/jo980289r
  7. Menges, F.; Neuburger, M.; Pfaltz, A. Org. Lett. 2002, 4, 4713. https://doi.org/10.1021/ol027253c
  8. Meiere, S. H.; Valahovic, M. T.; Harman, W. D. J. Am. Chem. Soc. 2002, 124, 15099. https://doi.org/10.1021/ja0118845
  9. Bhor, S.; Anilkumar, G.; Tse, M. K.; Klawonn, M.; Dobler, C.; Bitterlich, B.; Grotevendt, A.; Beller, M. Org. Lett. 2005, 7, 3393. https://doi.org/10.1021/ol050821e
  10. Lambardino, J. G.; Wiseman, E. H. J. Med. Chem. 1974, 17, 1182. https://doi.org/10.1021/jm00257a011
  11. Philips, A. P.; White, H. L.; Rosen, S. Eur. Pat. Appl. EP 58890, 1982.
  12. Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Keys, J. R.; Vatter, S. W. L.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. Nature 1994, 372, 739. https://doi.org/10.1038/372739a0
  13. Takle, A. K.; Brown, M. J. B.; Davies, S.; Dean, D. K.; Francis, G.; Gaiba, A.; Hird, A. W.; King, F. D.; Lovell, P. J.; Naylor, A.; Reith, A. D.; Steadman, J. G.; Wilson, D. M. Bioorg. Med. Chem. Lett. 2006, 16, 378. https://doi.org/10.1016/j.bmcl.2005.09.072
  14. de Laszlo, S. E.; Hacker, C.; Li, B.; Kim, D.; MacCoss, M.; Mantalo, N.; Pivnichny, J. V.; Colwell, L.; Koch, G. E.; Cascieri, M. A.; Hagmenn, W. K. Bioorg. Med. Chem. Lett. 1999, 9, 641.
  15. Schmierer, R.; Mildenberger, H.; Buerstell, H. German Patent 361464, 1987
  16. Schmierer, R.; Mildenberger, H.; Buerstell, H. Chem. Abstr. 1988, 108, 37838.
  17. Heeres, J.; Backx, L. J. J.; Mostmans, J. H.; Van Custem, J. J. Med. Chem. 1979, 22, 1003. https://doi.org/10.1021/jm00194a023
  18. Antolini, M.; Bozzoli, A.; Ghiron, C.; Kennedy, G.; Rossi, T.; Ursini, A. Bioorg. Med. Chem. Lett. 1999, 9, 1023. https://doi.org/10.1016/S0960-894X(99)00112-2
  19. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hui, Y.-H.; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinsky-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. J. Med. Chem. 2002, 45, 1697. https://doi.org/10.1021/jm010523x
  20. Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Buerstell, H.; Sachse, B. U.S. Patent 4820335, 1989
  21. Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Buerstell, H.; Sachse, B. Chem. Abstr. 1989, 111, 19494w.
  22. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. https://doi.org/10.1021/cr010338r
  23. Nara, S. J.; Naik, P. U.; Harjani, J. R.; Salunkhe, M. M. Indian J. Chem. 2001, 45B, 2257.
  24. Chowdhury, S.; Mohan, R. S.; Scott, J. L. Tetrahedron 2007, 63, 2363. https://doi.org/10.1016/j.tet.2006.11.001
  25. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. https://doi.org/10.1021/cr940472u
  26. Arnold, P. L.; Liddle, S. T. Chem. Commun. 2006, 3959.
  27. Ku hl, O. Chem. Soc. Rev. 2007, 36, 592. https://doi.org/10.1039/b603765h
  28. Radziszewski, B. Chem. Ber. 1882, 15, 1493. https://doi.org/10.1002/cber.18820150207
  29. Japp, F. R.; Robinson, H. H. Chem. Ber. 1882, 15, 1268. https://doi.org/10.1002/cber.188201501272
  30. Radziszewski, B. Chem. Ber. 1882, 15, 1493. https://doi.org/10.1002/cber.18820150207
  31. Japp, F. R.; Robinson, H. H. Chem. Ber. 1882, 15, 1268. https://doi.org/10.1002/cber.188201501272
  32. Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II, Vol. 3; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; p 77.
  33. Balalaie, S.; Arabanian, A.; Hashtroudi, M. S. Monatsh. Chem. 2000, 131, 945. https://doi.org/10.1007/s007060070049
  34. Sharma, G. V. M.; Jyothi, Y.; Lakshmi, P. S. Synth. Commun. 2006, 36, 2991. https://doi.org/10.1080/00397910600773825
  35. Heravi, M. M.; Bakhtiari, K.; Oskooie, H. A.; Taheri, S. J. Mol. Catal. A: Chem. 2007, 263, 279. https://doi.org/10.1016/j.molcata.2006.08.070
  36. Kidwai, M.; Mothsra, P.; Bansal, V.; Goyal, R. Monatsh. Chem. 2006, 137, 1189. https://doi.org/10.1007/s00706-006-0518-9
  37. Sangshetti, J. N.; Kokare, N. D.; Kothakar, S. A.; Shinde, D. B. Monatsh. Chem. 2008, 139, 125. https://doi.org/10.1007/s00706-007-0766-3
  38. Usyatinsky, A. Y.; Khmelnitsky, Y. L. Tetrahedron Lett. 2000, 41, 5031. https://doi.org/10.1016/S0040-4039(00)00771-1
  39. Wolkenberg, S. E.; Winoski, D. D.; Leister, W. H.; Wang, Y.; Zhoa, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453. https://doi.org/10.1021/ol049682b
  40. Kidwai, M.; Saxena, S.; Rastogi, S. Bull. Korean Chem. Soc. 2005, 26, 2051. https://doi.org/10.5012/bkcs.2005.26.12.2051
  41. Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. J. Mol. Catal. A: Chem. 2007, 263, 112. https://doi.org/10.1016/j.molcata.2006.08.048
  42. Sadeghi, B.; Mirjalili, B. B. F.; Hashemi, M. M. Tetrahedron Lett. 2008, 49, 2575. https://doi.org/10.1016/j.tetlet.2008.02.100
  43. Karimi, A. R.; Alimohammadi, Z.; Azizian, J.; Mohammadi, A. A.; Mohammadizadeh, M. R. Catal. Commun. 2006, 7, 728. https://doi.org/10.1016/j.catcom.2006.04.004
  44. Kantevari, S.; Vuppalapati, S. V. N.; Biradar, D. O.; Nagarapu, L. J. Mol. Catal. A: Chem. 2007, 266, 109. https://doi.org/10.1016/j.molcata.2006.10.048
  45. Samai, S.; Chandra Nandi, G.; Singh, P.; Singh, M. S. Tetrahedron 2009, 65, 10155. https://doi.org/10.1016/j.tet.2009.10.019
  46. Niknam, K.; Deris, A.; Naeimi, F.; Majleci, F. Tetrahedron Lett. 2011, 52, 4642. https://doi.org/10.1016/j.tetlet.2011.06.105
  47. Salehi, J., Khodaei, M. M.; Khosropour, A. R. Synthesis 2011, 459.
  48. Wang, L. M.; Wang, Y. H.; Tian, H.; Yao, Y. F.; Shao, J. H.; Liu, B. J. Fluorine Chem. 2006, 127, 1570. https://doi.org/10.1016/j.jfluchem.2006.08.005
  49. Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39, 3772. https://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
  50. Khodaei, M. M.; Khosropour, A. R.; Kookhazadeh, M. Can. J. Chem. 2005, 83, 209. https://doi.org/10.1139/v05-021
  51. Veisi, H. Synlett 2007, 2607.
  52. Veisi, H. Synthesis 2010, 2631.
  53. Veisi, H. Tetrahedron Lett. 2010, 2109.
  54. Veisi, H.; Ghorbani-Vaghei, R. Tetrahedron 2010, 7445.
  55. Khazaei, A; Rahmati, S.; Rostami, A. Helv Chem. Acta 2009, 92, 1434. https://doi.org/10.1002/hlca.200900002
  56. Rostami, A.; Rahmati, S.; Khazaei, A. Monatsh Chem. 2009, 140, 663. https://doi.org/10.1007/s00706-009-0117-7
  57. Khazaei, A.; Zolfigol, M. A.; Rostami, A.; Ghorbani Choghamarani, A. Catal. commun. 2007, 8, 543. https://doi.org/10.1016/j.catcom.2006.06.018
  58. Khazaei, A.; Zolfigol, M. A.; Tanbakouchian, Z.; Shiri, M.; Niknam, K.; Saien, J. Catal. Commun. 2007, 8, 917. https://doi.org/10.1016/j.catcom.2006.07.012
  59. Veisi, H. Curr. Org. Chem. 2011, 15, 2438. https://doi.org/10.2174/138527211796150570
  60. Uchida, H.; Shimizu, T.; Reddy, P. Y.; Nakamura, S.; Toru, T. Synthesis 2003, 1236.

Cited by

  1. -imidazole vol.69, pp.1, 2013, https://doi.org/10.1107/S1600536812049100
  2. Green synthesis of 5-arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium vol.35, pp.3, 2014, https://doi.org/10.1080/17415993.2013.860142
  3. Transition metal-free one-pot synthesis of nitrogen-containing heterocycles vol.20, pp.1, 2016, https://doi.org/10.1007/s11030-015-9596-0
  4. Synthesis and biological evaluation of 1,2,4,5-tetrasubstituted imidazoles vol.43, pp.8, 2017, https://doi.org/10.1007/s11164-017-2886-7
  5. Facile, eco-friendly, one-pot protocol for the synthesis of indole-imidazole derivatives catalyzed by amino acids vol.47, pp.16, 2017, https://doi.org/10.1080/00397911.2017.1332766
  6. Nano-sized Cu/Zn-modified MCM-41 (Cu/Zn-MCM-41): preparation, characterization and catalytic application in a new more atom efficient synthesis of tetrasubstituted imidazoles pp.1573-4854, 2017, https://doi.org/10.1007/s10934-017-0422-1
  7. Synthesized 2,4,5-Triphenylimidazole as Precursor of Organic Light Emitting Diode (OLED) Material vol.896, pp.1662-8985, 2014, https://doi.org/10.4028/www.scientific.net/AMR.896.468
  8. Synthesis, antimicrobial evaluation and docking study of triazole containing triaryl-1H-imidazole vol.49, pp.11, 2012, https://doi.org/10.1080/00397911.2019.1600192