Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

(PhIO)n Mediated Annulations of Aromatic Aldehyde N-Acylhydrazones for the Synthesis of 1,3,4-Oxadiazoles

  • Shang, Zhenhua (College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering) ;
  • Ha, Jing (College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering) ;
  • Tao, Xiao (College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering) ;
  • Xu, Longpeng (College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering) ;
  • Liu, Qing (College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering) ;
  • Wang, Pan (College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Hebei Research Center of Pharmaceutical and Chemical Engineering)
  • Received : 2013.12.19
  • Accepted : 2013.03.08
  • Published : 2013.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Ogata, M.; Atobe, H.; Kushida, H.; Yamamoto, K. J. Antibiot. 1971, 24, 443. https://doi.org/10.7164/antibiotics.24.443
  2. Vardan, S.; mookherjee, S.; Eich, R. Clin. Pharm. Ther. 1983, 34(3), 290. https://doi.org/10.1038/clpt.1983.170
  3. Summa, V.; Petrocchi, A.; Bonelli, F.; Crescenzi, B.; Donghi, M.; Ferra, M.; Fiore, F.; Gardelli, C.; Gonzalez Paz, O.; Hazuda, D. J.; Jones, P.; Kinzel,O.; Laufer, R.; Monteagudo, E.; Muraglia, E.; Nizi, E.; Orvieto, F.; Pace,P.; Pescatore, G.; Scarpelli, R.; Stillmock, K.; Witmer, M. V.; Rowley, M. J. J. Med. Chem. 2008, 51, 5843. https://doi.org/10.1021/jm800245z
  4. Brown, A. R.; Bradley, D. D. C.; Burns, P. L.; Burroughes, J. H.; Friend, R. H.; Greenham, N. C.; Burn, P. L.; Holmes, A. B.; Kraft, A. Appl. Phys. Lett. 1992, 61, 2793. https://doi.org/10.1063/1.108094
  5. Golfier, M.; Guillerez, M. G. Tetrahedron Lett. 1976, 17, 267. https://doi.org/10.1016/S0040-4039(00)93704-3
  6. John, P. I.; Kathleen, S. G.; John, T. G.; Glenn, N. C. J. Chem. Eng. Data 1988, 33, 385. https://doi.org/10.1021/je00053a044
  7. Bentiss, F.; Largrene, M. J. Heterocycl. Chem. 1999, 36, 1029. https://doi.org/10.1002/jhet.5570360433
  8. Loffler, J.; Schobert, R. Synlett. 1997, 283.
  9. El Kaim, L.; Le Menestrel, I.; Morgentin, R. Tetrahedron Lett. 1998, 39, 6885. https://doi.org/10.1016/S0040-4039(98)01503-2
  10. Isobe, T.; Ishikawa, T. J. Org. Chem. 1999, 64, 6989. https://doi.org/10.1021/jo9909756
  11. Brain, C. T.; Paul, J. M.; Loong, Y.; Oakley, P. J. Tetrahedron Lett. 1999, 40, 327.
  12. Park, Y.-D.; Kim, J.-J.; Chung, H.-A.; kweon, D.-H.; Cho, S.-D.; Lee, S.-G.; Yoon, Y.-J. Synthesis 2003, 560.
  13. Yang, Y.-H.; Shi, M. Tetrahedron Lett. 2005, 46, 6285. https://doi.org/10.1016/j.tetlet.2005.07.048
  14. Rajapakse, H. A.; Zhu, H.; Young, M. B.; Mott, B. T. Tetrahedron Lett. 2006, 47, 4827. https://doi.org/10.1016/j.tetlet.2006.05.051
  15. Kangani, C. O.; Kelley, D. E.; Day, B. W. Tetrahedron Lett. 2006, 47, 6497. https://doi.org/10.1016/j.tetlet.2006.07.032
  16. Li, C.-K.; Dickson, H. D. Tetrahedron Lett. 2009, 50, 6435. https://doi.org/10.1016/j.tetlet.2009.08.084
  17. Nagendra, G.; Lamani, R. S.; Narendra, N.; Sureshbabu, V. V. Tetrahedron Lett. 2010, 51, 6338. https://doi.org/10.1016/j.tetlet.2010.09.122
  18. Pouliot, M. F.; Angers, L.; Hamel, J. D.; Paquin, J. F. Org. Biomol.Chem. 2012, 10, 988. https://doi.org/10.1039/c1ob06512b
  19. Stolle, R. J. Prakt. Chem. 1906, 73, 277.
  20. Milcent, R.; Barbier, G. J. Heterocyclic Chem. 1983, 20, 77. https://doi.org/10.1002/jhet.5570200118
  21. Reddy, P. S. N.; Reddy, P. P. Indian J. Chem. 1987, 26B, 890.
  22. Narayana,B.; Ashalatha, B. V.; Vijaya Raj, K. K.; Fernandesb, J.; Sarojinic, B. K. Bioorg. & Med. Chem. 2005, 13(15), 4638. https://doi.org/10.1016/j.bmc.2005.04.068
  23. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Bahramnejad, M. Tetrahedron Lett. 2006, 47, 6983. https://doi.org/10.1016/j.tetlet.2006.07.127
  24. Guin, S.; Ghosh, T.; Rout, S. K.; Banerjee, A.; Patel, B. K. Org. Lett. 2011, 13, 5976. https://doi.org/10.1021/ol202409r
  25. Gibson, M. S. Tetrahedron 1962, 18, 1377. https://doi.org/10.1016/S0040-4020(01)99292-0
  26. Yang, R.-Y.; Dai, L.-X. J. Org. Chem. 1993, 58, 3381. https://doi.org/10.1021/jo00064a027
  27. Jedlovska, E.; Lesko, J. Synth. Commun. 1994, 24, 1879. https://doi.org/10.1080/00397919408010196
  28. Souldozi, A.; Ramazani, A. Tetrahedron Lett. 2007, 48, 1549. https://doi.org/10.1016/j.tetlet.2007.01.021
  29. Pore, D. M.; Mahadik, S. M.; Desai, U. V. Synth. Commun. 2008, 38, 3121. https://doi.org/10.1080/00397910802054289
  30. Dobrota, C.; Paraschivescu, C. C.; Dumitru, I.; Matache, M.; Baciu, I.; Rupa, L. L. Tetrahedron Lett. 2009, 50, 1886. https://doi.org/10.1016/j.tetlet.2009.02.054
  31. Ramazani, A.; Rezaei, A. Org. Lett. 2010, 12, 2852. https://doi.org/10.1021/ol100931q
  32. Chiba, T.; Okimoto, M. J. Org. Chem. 1992, 57, 1375. https://doi.org/10.1021/jo00031a014
  33. Shang, Z.-H.; Reiner, J.; Chang, J.-B.; Zhao, K. Tetrahedron Lett. 2005, 46, 2701. https://doi.org/10.1016/j.tetlet.2005.02.067
  34. Shang, Z.-H. Synth. Commun. 2006, 36, 2927. https://doi.org/10.1080/00397910600773650
  35. Chen, H.-J.; Shang, Z.-H.; Chang, J.-B. Synth. Commun. 2006, 36, 445. https://doi.org/10.1080/00397910500383501
  36. Zefirov, N. S.; Caple, R.; Palyulin, V. A.; Berglund, B.; Tykwinski, R.; Zhdankin, V. V.; Kozmin, A. S. Izv. Akad. Nauk SSSR 1988, 1452.
  37. Kim, D. Y.; Mang, J. Y.; Oh, D. Y. Synth. Commun. 1994, 24(5), 629. https://doi.org/10.1080/00397919408012639
  38. Schardt, B. C.; Hill, C. L. Inorg. Chem. 1983, 22, 1563. https://doi.org/10.1021/ic00152a030
  39. Leca, D.; Song, K.; Amatore, M.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Eur. J. 2004, 10, 906. https://doi.org/10.1002/chem.200305525
  40. Okimoto, M.; Chiba, T. J. Org. Chem. 1990, 55, 1070. https://doi.org/10.1021/jo00290a048
  41. Bentiss, F.; Largrenee, M. J. Heterocycl. Chem. 1999, 36, 1029. https://doi.org/10.1002/jhet.5570360433
  42. Pardeshi, S. P.; Patil, S. S.; Bobade, V. D. Synth. Commun. 2010, 40, 1601. https://doi.org/10.1080/00397910903134592
  43. Paolo Stabile, P.; Lamonica, A.; Ribecai, A.; Castoldi, D.; Guercio, G.; Curcuruto, O. Tetrahedron Lett. 2010, 51, 4801. https://doi.org/10.1016/j.tetlet.2010.06.139

Cited by

  1. Mediated Annulations of Aromatic Aldehyde N-Acylhydrazones for the Synthesis of 1,3,4-Oxadiazoles. vol.44, pp.40, 2013, https://doi.org/10.1002/chin.201340135
  2. Synthesis, Characterization and Energetic Properties of 1,3,4‐Oxadiazoles vol.2015, pp.23, 2013, https://doi.org/10.1002/ejoc.201500583