Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Facile One-Pot Synthesis of Cinnamamides from Aromatic Aldehydes and Acetonitrile with Me3SiOK

  • Lee, Hyun-Seung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Sung-Hwan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Received : 2011.02.28
  • Accepted : 2011.03.15
  • Published : 2011.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Davies, I. R.; Cheeseman, M.; Niyadurupola, D. G.; Bull, S. D. Tetrahedron Lett. 2005, 46, 5547-5549. https://doi.org/10.1016/j.tetlet.2005.06.027
  2. Williams, P. G.; Asolkar, R. N.; Kondratyuk, T.; Pezzuto, J. M.; Jensen, P. R.; Fenical, W. J. Nat. Prod. 2007, 70, 83-88. https://doi.org/10.1021/np0604580
  3. Park Choo, H.-Y.; Peak, K.-H.; Park, J.; Kim, D. H.; Chung, H. S. Eur. J. Med. Chem. 2000, 35, 643-648. https://doi.org/10.1016/S0223-5234(00)00158-6
  4. Concellon, J. M.; Rodriguez-Solla, H.; Concellon, C.; Simal, C.; Alvaredo, N. J. Org. Chem. 2010, 75, 3451-3453. https://doi.org/10.1021/jo100320j
  5. Feng, S.; Zhang, Z.; Jiang, S.; Yu, X. J. Chem. Res. 2010, 382-384.
  6. Petrova, J.; Momchilova, S.; Vassilev, N. G. Phosphorus, Sulfur and Silicon 2000, 164, 87-94. https://doi.org/10.1080/10426500008045236
  7. Kojima, S.; Inai, H.; Hidaka, T.; Ohkata, K. Chem. Commun. 2000, 1795-1796.
  8. Jiang, S.; Yang, K.; Yu, X. Synth. Commun.2009, 39, 1759-1767. https://doi.org/10.1080/00397910802590902
  9. Zheng, J.; Wang, Z.; Shen, Y. Synth. Commun. 1992, 22, 1611-1617. https://doi.org/10.1080/00397919208021635
  10. Kojima, S.; Kawaguchi, K.; Matsukawa, S.; Uchida, K.; Akiba, K.-y. Chem. Lett. 2002, 170- 171.
  11. Ishino, Y.; Mihara, M.; Nishihama, S.; Nishiguchi, I. Bull. Chem. Soc. Jpn. 1998, 71, 2669-2672. https://doi.org/10.1246/bcsj.71.2669
  12. Hernandez-Fernandez, E.; Fernandez-Zertuche, M.; Garcia-Barradas, O.; Munoz-Muniz, O.; Ordonez, M. Synlett 2006, 440-444.
  13. Kojima, S.; Inai, H.; Hidaka, T.; Fukuzaki, T.; Ohkata, K. J. Org. Chem. 2002, 67, 4093-4099. https://doi.org/10.1021/jo0161936
  14. Weidlich, T.; Prokes, L.; Ruzicka, A.; Padelkova, Z. Monatsh Chem. 2010, 141, 205-211. https://doi.org/10.1007/s00706-009-0248-x
  15. Borhade, S. R.; Waghmode, S. B. Tetrahedron Lett. 2008, 49, 3423-3429. https://doi.org/10.1016/j.tetlet.2008.03.109
  16. Tian, J.; Moeller, K. D. Org. Lett. 2005, 7, 5381-5383. https://doi.org/10.1021/ol0519487
  17. Botella, L.; Najera, C. J. Org. Chem. 2005, 70, 4360-4369. https://doi.org/10.1021/jo0502551
  18. Zapf, A.; Beller, M. Chem. Eur. J. 2001, 7, 2908-2915. https://doi.org/10.1002/1521-3765(20010702)7:13<2908::AID-CHEM2908>3.0.CO;2-R
  19. Concellon, J. M.; Bardales, E. J. Org. Chem. 2003, 68, 9492-9495. https://doi.org/10.1021/jo0349577
  20. Concellon, J. M.; Bardales, E. Eur. J. Org. Chem. 2004, 1523-1526.
  21. Xu, J.; Burton, D. J. J. Org. Chem. 2005, 70, 4346-4353. https://doi.org/10.1021/jo050314a
  22. Park, J. H.; Kim, S. Y.; Kim, S. M.; Chung, Y. K. Org. Lett. 2007, 9, 2465- 2468. https://doi.org/10.1021/ol0706760
  23. Schleicher, K. D.; Jamison, T. F. Org. Lett. 2007, 9, 875- 878. https://doi.org/10.1021/ol063111x
  24. Uenoyama, Y.; Fukuyama, T.; Nobuta, O.; Matsubara, H.; Ryu, I. Angew. Chem. Int. Ed. 2005, 44, 1075-1078. https://doi.org/10.1002/anie.200461954
  25. Cao, L.; Ding, J.; Gao, M.; Wang, Z.; Li, J.; Wu, A. Org. Lett. 2009, 11, 3810-3813. https://doi.org/10.1021/ol901250c
  26. Gartner, Z. J.; Grubina, R.; Calderone, C. T.; Liu, D. R. Angew. Chem. Int. Ed. 2003, 42, 1370-1375. https://doi.org/10.1002/anie.200390351
  27. Kim, E. S.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 1589-1591. https://doi.org/10.1016/j.tetlet.2010.01.063
  28. Kim, E. S.; Kim, H. S.; Kim, J. N. Tetrahedron Lett. 2009, 50, 2973-2975. https://doi.org/10.1016/j.tetlet.2009.04.007
  29. Kim, E. S.; Lee, H. S.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6286-6289. https://doi.org/10.1016/j.tetlet.2009.08.127
  30. Merchant, K. J. Tetrahedron Lett. 2000, 41, 3747-3749. https://doi.org/10.1016/S0040-4039(00)00482-2
  31. Ko, E. Y.; Lim, C. H.; Chung, K.-H. Bull. Korean Chem. Soc. 2006, 27, 432-434. https://doi.org/10.5012/bkcs.2006.27.3.432
  32. Chung, K.-H.; Moon, B.-C.; Lim, C. H.; Kim, J. P.; Lee, J. H.; Chi, D. Y. Bull. Korean Chem. Soc. 2006, 27, 1203-1205. https://doi.org/10.5012/bkcs.2006.27.8.1203
  33. Cai, M.-Z.; Zhao, H.; Hu, W.-Y. Chin. J. Chem. 2005, 23, 443- 447. https://doi.org/10.1002/cjoc.200590443
  34. Bernini, R.; Cacchi, S.; Salve, I. D.; Fabrizi, G. Synlett 2006, 2947-2952.
  35. Sasho, S.; Harakawa, H.; Kamisaka, N.; Miki, I.; Kuno, Y.; Kumazawa, T.; Sekine, S. 1997, JP 09087237A; Chem. Abstr. 1997, 127, 17675.

Cited by

  1. ChemInform Abstract: Facile One-Pot Synthesis of Cinnamamides from Aromatic Aldehydes and Acetonitrile with Me3SiOK. vol.42, pp.43, 2011, https://doi.org/10.1002/chin.201143075
  2. Quantification and Comparison of Extraction Methods for Alkaloids in Aegle marmelos Leaves by HPLC vol.9, pp.7, 2011, https://doi.org/10.1177/1934578x1400900725
  3. Simple Synthesis of New 3-Substituted 4-(3-Chloro-4-fluorophenyl)-1H-pyrrole Derivatives and Their Anticancer Activity in Vitro vol.89, pp.2, 2014, https://doi.org/10.3987/com-13-12890