Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Convenient Synthesis of New 3,7-Diphenylthieno[3,2-e]bis[1,2,4] triazolo[4,3-a:4',3'-c]pyrimidine Derivatives by Oxidative Cyclization Using Alumina-supported Calcium Hypochlorite

  • Received : 2010.05.15
  • Accepted : 2010.06.15
  • Published : 2010.08.20
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Abstract

New 3,7-diphenylthieno[3,2-e]bis[1,2,4]triazolo[4,3-a:4',3'-c]pyrimidine derivatives were easily synthesized at room temperature in good yield by the oxidative cyclization of thienopyrimidinyl hydrazones with alumina-supported calcium hypochlorite ($Ca(OCl)_2/Al_2O_3$).

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References

  1. El-Hawash, S. A.; Habib, N. S.; Fanaki, N. H. Pharmazie 1999, 54, 808.
  2. Dickinson, R. P.; Bell, A. W.; Hitchcock, C. A.; Narayama-Swami, S.; Ray, S. J.; Richardson, K.; Troke, P. F. Bioorg. Med. Chem. Lett. 1996, 6, 2031. https://doi.org/10.1016/0960-894X(96)00363-0
  3. Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N. T.; Altinok, G. Farmaco 2002, 57, 101. https://doi.org/10.1016/S0014-827X(01)01176-4
  4. Tehranchian, S.; Akbarzadeh, T.; Fazeli, M. R.; Jamalifar, H.; Shafiee, A. Bioorg. Med. Chem. Lett. 2005, 15, 1023. https://doi.org/10.1016/j.bmcl.2004.12.039
  5. Nagamatsu, T.; Ahmed, S.; Hossion, A. M. L.; Ohno, S. Heterocycles 2007, 73, 777. https://doi.org/10.3987/COM-07-S(U)58
  6. Shawali, A. S.; Hassaneen, H. M.; Shurrab, N. K. Tetrahedron 2008, 64, 10339. https://doi.org/10.1016/j.tet.2008.08.082
  7. Prakash, O.; Kumar, R.; Tyagi, P.; Kuhad, R. C. Eur. J. Med. Chem. 2007, 42, 868. https://doi.org/10.1016/j.ejmech.2006.11.019
  8. Joe, B. S.; Son, H. Y.; Song, Y.-H. Heterocycles 2008, 75, 3091. https://doi.org/10.3987/COM-08-11465
  9. Gibson, M. S. Tetrahedron 1963, 19, 1587. https://doi.org/10.1016/S0040-4020(01)99232-4
  10. Gibson, M. S. Tetrahedron 1963, 19, 1587. https://doi.org/10.1016/S0040-4020(01)99232-4
  11. El-Gazzar, A. B.; Hassan, N. A. Molecules 2000, 5, 835. https://doi.org/10.3390/50600835
  12. Abdel-Fattah, B.; Kandeel, M. M.; Abdel-Hakeem, M.; Fahmy, Z. M. J. Chin. Chem. Soc. 2006, 53, 403. https://doi.org/10.1002/jccs.200600051
  13. Bower, J. D.; Doyle, F. P. J. Chem. Soc. 1957, 727. https://doi.org/10.1039/jr9570000727
  14. Hozein, Z. A.; Atta, F. M.; Hassan, Kh. M.; Abdel-Wahab, A. A.; Ahmed, S. A. Synth. Commun. 1996, 26, 3733. https://doi.org/10.1080/00397919608003791
  15. Shawali, A. S.; Hassaneen, H. M.; Shurrab, N. K. Heterocycles 2008, 75, 1479. https://doi.org/10.3987/COM-07-11311
  16. Shawali, A. S.; Gomha, S. M. Tetrahedron 2002, 58, 8559. https://doi.org/10.1016/S0040-4020(02)00946-8
  17. Bourgeois, P.; Cantegril, R.; Chene, A.; Gelin, J.; Mortier, J.; Moyroud, J. Synth. Commun. 1993, 23, 3195. https://doi.org/10.1080/00397919308011179
  18. Ciesielski, M.; Pufky, D.; Döring, M. Tetrahedron 2005, 61, 5942. https://doi.org/10.1016/j.tet.2005.01.111
  19. Song, Y.-H.; Son, H. Y. J. Heterocycl. Chem. 2010, 47, in press.
  20. Lee, H. M.; Song, Y.-H. Bull. Korean Chem. Soc. 2010, 31, 185. https://doi.org/10.5012/bkcs.2010.31.01.185
  21. Son, H. Y.; Song, Y.-H. J. Kor. Chem. Soc. 2010, 54, 350. https://doi.org/10.5012/jkcs.2010.54.3.350
  22. Jo, B. S.; Song, Y.-H. Synth. Commun. 2009, 39, 4407. https://doi.org/10.1080/00397910902906545
  23. Song, Y.-H.; Jo, B. S. J. Heterocycl. Chem. 2009, 46, 1132. https://doi.org/10.1002/jhet.186
  24. Song, Y.-H.; Jo, B. S.; Lee, H. M. Heterocycl. Commun. 2009, 15, 203.
  25. Song, Y.-H.; Jo, B. S. Bull. Korean Chem. Soc. 2009, 30, 969. https://doi.org/10.5012/bkcs.2009.30.4.969
  26. Lee, H. M.; Song, Y.-H. J. Kor. Chem. Soc. 2009, 53, 387. https://doi.org/10.5012/jkcs.2009.53.3.387
  27. Song, Y.-H.; Seo, J. J. Heterocycl. Chem. 2007, 44, 1439. https://doi.org/10.1002/jhet.5570440631
  28. Song, Y.-H. Heterocycl. Commun. 2007, 13, 33.
  29. Shiho, D.; Tagami, S. J. Am. Chem. Soc. 1960, 82, 4044. https://doi.org/10.1021/ja01500a058
  30. Robba, M.; Lecomte, J.-M.; Cugnon de Sévricourt, M. Comptes rendus 1968, 266 (Serie C), 128.
  31. Jourdan, F.; Renault, J.; Karamat, A.; Ladurée, D.; Robba, M. J. Heterocycl. Chem. 1995, 32, 953. https://doi.org/10.1002/jhet.5570320347

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