Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Aromatization of 1,3,5-Trisubstituted of 4,5-Dihydro-1H-Pyrazoles by In-Situ Generation of I+ from Hydrogen Peroxide/Acids/Iodide Potassium or Sodium Systems

  • Maleki, Behrooz (Department of Chemistry, Sabzevar Tarbiat Moallem University) ;
  • Veisi, Hojat (Department of Chemistry, Payame Noor University)
  • Received : 2011.07.04
  • Accepted : 2011.10.18
  • Published : 2011.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

A simple, green and cost-effective protocol was used for the aromatization of 1,3,5-trisubstituted-2-pyrazolines to the corresponding pyrazoles by in situ generation of iodine ($I^+$) from $H_2O_2$/AcOH or SSA or oxalic acid /KI or NaI system under thermal condition with moderate to good yields.

Keywords

References

  1. Taylor, E. C.; Patel, H.; Kumar, H. Tetrahedron 1992, 48, 8089. https://doi.org/10.1016/S0040-4020(01)80479-8
  2. Mohd, S.; Khan, S.; Alam, M. J. Chil. Chem. Soc. 2009, 54, 372.
  3. Deng, L.; Tao, W.; Lv, J.; Wang, W. J. Heterocycl. Chem. 2009, 46, 640. https://doi.org/10.1002/jhet.119
  4. Elguero, J. Pyrazoles. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Ress, C. W., Seriven, E. F. V., Pergamon: Oxford, UK, 1996; p 1-76.
  5. Yet, L. Pyrazole. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Seriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon: Oxford, UK, 2008; p 1-141.
  6. Rajendera, P. Y.; Lakshmana, R. A.; Prasoona, L.; Murali, K.; Ravi, K. P. Bioorg. Med. Chem. Lett. 2005, 15, 5030. https://doi.org/10.1016/j.bmcl.2005.08.040
  7. Bansal, E.; Srivatsava, V. K.; Kumar, A. Eur. J. Med. Chem. 2001, 36, 81. https://doi.org/10.1016/S0223-5234(00)01179-X
  8. Ahn, J. H.; Kim, H. M.; Jungs, S. H.; Kang, S. K.; Kim, K. R.; Rhee, S. D.; Yang, S. D.; Cheon, H. G.; Kim, S. S. Bioorg. Med. Chem. Lett. 2004, 14, 4461. https://doi.org/10.1016/j.bmcl.2004.06.046
  9. Deng, L.; Tao, W.; Lv, J.; Wang, W. J. Heterocycl. Chem. 2009, 46, 640. https://doi.org/10.1002/jhet.119
  10. Azarifar, D.; Maleki, B. J. Heterocycl. Chem. 2005, 42, 157. https://doi.org/10.1002/jhet.5570420125
  11. Maleki, B.; Azarifar, D.; Khodaverdian Moghaddam, M.; Hojati, S. F.; Gholizadeh, M.; Salehabadi, H. J. Serb. Chem. Soc. 2009, 74, 1371. https://doi.org/10.2298/JSC0912371M
  12. Kumar, A.; Maurya, A. R.; Sharma, S. Bioorg. Med. Chem. Lett. 2009, 19, 4432. https://doi.org/10.1016/j.bmcl.2009.05.056
  13. Han, B.; Liu, Z.; Liu, Q.; Yang, L.; Li-Liu, Z.; Yu, W. Tetrahedron 2006, 62, 2492. https://doi.org/10.1016/j.tet.2005.12.056
  14. Chai, F. L.; Zhao, Y.; Sheng, O. Z.; Liu, O. Tetrahedron Lett. 2006, 47, 9283. https://doi.org/10.1016/j.tetlet.2006.10.108
  15. Wentao, W.; Rui, L.; Qiang, L.; Longmin, W. Chin. J. Org. Chem. 2009, 2, 283.
  16. Nakamichi, N.; Kawashita, Y.; Hayashi, M. Org. Lett. 2002, 4, 3955. https://doi.org/10.1021/ol0268135
  17. Sabitha, G.; Reddy, G. S. K.; Reddy, C. S.; Fatima, N.; Yadav, J. S. Synthesis 2003, 8, 1267.
  18. Shah, J. N.; Shah, C. K. J. Org. Chem. 1978, 43, 1266. https://doi.org/10.1021/jo00400a060
  19. Singh, S. P.; Kumar, D.; Prakash, O.; Kapoor, R. P. Synth. Commun. 1997, 27, 2673.
  20. Gladstone, W. A.; Norman, R. O. C. J. Chem. Soc. Chem. Commun. 1966, 1536.
  21. Bhantnagar, I.; George, M. V. Tetrahedron 1968, 24, 1293. https://doi.org/10.1016/0040-4020(68)88080-9
  22. Smith, L. I.; Howard, K. L. J. Am. Chem. Soc. 1943, 65, 159. https://doi.org/10.1021/ja01242a008
  23. Dodwadmath, R. P.; Wheeler, T. S. Proc. Ind. Acad. Sci. 1935, 2A, 438.
  24. Azarifar, D.; Zolfigol, M. A.; Maleki, B. Synthesis 2004, 11, 1744.
  25. Azarifar, D.; Zolfigol, M. A.; Maleki, B. Bull. Korean Chem. Soc. 2004, 25, 23. https://doi.org/10.5012/bkcs.2004.25.1.023
  26. Zolfigol, M. A.; Azarifar, D.; Maleki, B. Tetrahedron Lett 2004, 45, 2183.
  27. Azarifar, D.; Maleki, B. J. Chin. Chem. Soc. 2005, 52, 1215.
  28. Ghorbani-Vaghei, R.; Azarifar, D.; Khazaei, A.; Maleki, B. Phosphrous, Sulfur and Silicon. 2004, 179, 1877. https://doi.org/10.1080/10426500490466797
  29. Ghorbani-Vaghei, R.; Azarifar, D.; Maleki, B. Bull. Korean Chem. Soc. 2004, 25, 953. https://doi.org/10.5012/bkcs.2004.25.7.953
  30. Ghorbani-Vaghei, R.; Azarifar, D.; Maleki, B. J. Chin. Chem. Soc. 2004, 51, 1373.
  31. Azarifar, D.; Maleki, B. Heterocycles 2005, 65, 865. https://doi.org/10.3987/COM-04-10276
  32. Zolfigol, M. A.; Azarifar, D.; Mallakpour, S.; Mohammadpoor- Baltork, I.; Forghania, A.; Maleki, B.; Abdollahi-Alibeik, M. Tetrahedron Lett. 2006, 47, 833. https://doi.org/10.1016/j.tetlet.2005.11.088
  33. Azarifar, D.; Nadimi, E.; Ghorbani-Vaghei, R.; Maleki, B. Mendeleev Commun. 2006, 330.
  34. Azarifar, D.; Maleki, B. Synth. Commun. 2005, 35, 2581. https://doi.org/10.1080/00397910500214136
  35. Azarifar, D.; Maleki, B.; Sahraei, M. J. Heterocycl. Chem. 2008, 45, 563. https://doi.org/10.1002/jhet.5570450241
  36. Azarifar, D.; Maleki, B.; Setayeshnazar, M. Heterocycles 2008, 74, 865.
  37. Mamedov, V. A.; Mustakimova, L. V.; Gubaidullin, A. T.; Vdovina, S. V.; Litvinov, I. A.; Reznik, V. S. Chem. Heterocycl. Comp. 2006, 42, 1229. https://doi.org/10.1007/s10593-006-0230-z
  38. Azarifar, D.; Pirhayati, M.; Maleki, B.; Sanginabadi, M.; Nejat- Yami, R. J. Serb. Chem. Soc. 2010, 75, 1181. https://doi.org/10.2298/JSC090901096A
  39. Azarifar, D.; Maleki, B.; Setayeshnazar, M. Phosphorus, Sulfur and Silicon. 2009, 184, 2097. https://doi.org/10.1080/10426500802423933
  40. Sharma, S. D.; Hazarika, P.; Konwar, D. Catal. Commun. 2008, 9, 709. https://doi.org/10.1016/j.catcom.2007.08.008
  41. Fazlinia, A.; Mosslemin, H.; Sadoughi, H. J. Korean. Chem. Soc. 2010, 54, 579. https://doi.org/10.5012/jkcs.2010.54.5.579
  42. Narender, N.; Mohan, K. V. V. K.; Reddy, R. V.; Srinivasu, P.; Kulkarni, S. J.; Raghavan, K. V. J. Mol. Catal. A: Chem. 2003, 192, 73. https://doi.org/10.1016/S1381-1169(02)00131-0
  43. Ahn, K. H.; Choi, S.; Nam, H. J.; Byeon, S. H. Bull. Korean Chem. Soc. 2009, 30, 341.
  44. Hosseinzadeh, R.; Tajbaksh, M.; Lasemi, Z.; Sharifi, A. Bull. Korean Chem. Soc. 2004, 25, 1142.
  45. Zolfigol, M. A. Tetrahedron 2001, 57, 9501.
  46. Nikoorazm, M.; Ghorbani-Choghamarani, A.; Goudarziafshar, H.; Mallakpour, S. Bull. Korean Chem. Soc. 2010, 31, 2389. https://doi.org/10.5012/bkcs.2010.31.8.2389
  47. Niralwad, K. S.; Shingate, B. B.; Shingare, M. Bull. Korean Chem. Soc. 2010, 31, 981. https://doi.org/10.5012/bkcs.2010.31.04.981
  48. Nikoorazm, M.; Ghorbani-Choghamarani, A.; Goudarziafshar, H. Bull. Korean Chem. Soc. 2009, 30, 3120. https://doi.org/10.5012/bkcs.2009.30.12.3120
  49. Mirjalili, B. F.; Bamoniri, A.; Vafazadeh, R.; Zamani, L. Bull. Korean Chem. Soc. 2009, 30, 2440. https://doi.org/10.5012/bkcs.2009.30.10.2440
  50. Ghorbani-Choghamarani, A.; Nikoorazm, M.; Goudarziafshar, H.; Thamasbi, B. Bull. Korean Chem. Soc. 2009, 30, 1388. https://doi.org/10.5012/bkcs.2009.30.6.1388
  51. Alizadeh, A.; Khodaei, M. M.; Nazari, E. Bull. Korean Chem. Soc. 2007, 28, 1854. https://doi.org/10.5012/bkcs.2007.28.10.1854
  52. Maleki, B. Collect. Czech. Chem. Commun. 2011, 76, 27. https://doi.org/10.1135/cccc2010111
  53. Shirini, F.; Zolfigol, M. A.; Mohammadi, K. Bull. Korean Chem. Soc. 2004, 25, 325. https://doi.org/10.5012/bkcs.2004.25.2.325
  54. Mirjalili, B. F.; Zolfigol, M. A.; Bamoniri, A.; Zarei, A. Bull. Korean Chem. Soc. 2003, 24, 400. https://doi.org/10.5012/bkcs.2003.24.3.400
  55. Maleki, B.; Salehabadi, H.; Khodaverdian Moghaddam, M. Acta Chim. Slov. 2010, 57, 741.
  56. Kokare, N. D.; Sangshetti, J. N.; Shinde, D. B. Synthesis 2007, 18, 2829.
  57. Apelian, M. R.; Fung, A. S.; Kennedy, G. J.; Degnan, T. F. J. Phys. Chem. 1996, 100, 16577. https://doi.org/10.1021/jp960376s
  58. Hasaninejad, A.; Zare, A.; Mohammadizadeh, M. A.; Shekouhy, M. Arkivoc 2008, 13, 28.

Cited by

  1. Synthesis of Polysubstituted Iodobenzene Derivatives from Alkynylsilanes and 1,3-Dienes via Diels–Alder/Oxidation/Iodination Reaction Sequence vol.17, pp.7, 2015, https://doi.org/10.1021/acs.orglett.5b00306
  2. Oxidative Aromatization of 1,3,5-trisubstituted 2-pyrazolines Using Oxalic Acid/Sodium Nitrite System pp.1563-5333, 2017, https://doi.org/10.1080/10406638.2016.1267019
  3. Nano α-Al2O3supported ammonium dihydrogen phosphate (NH4H2PO4/Al2O3): preparation, characterization and its applicati vol.4, pp.81, 2011, https://doi.org/10.1039/c4ra07813f