DOI QR코드

DOI QR Code

New Synthesis of Thioflavones by the Regioselective Cyclization of 1-(2-Benzylthio)phenyl-3-phenylprop-2-yn-1-ones Using Hydrobromic Acid

  • Lee, Jae In (Department of Chemistry, College of Science and Technology, Duksung Women's University)
  • 투고 : 2020.04.10
  • 심사 : 2020.05.08
  • 발행 : 2020.08.20

초록

키워드

참고문헌

  1. Nakazumi, H.; Ueyama, T.; Kitao, T. J. Heterocyclic Chem. 1984, 21, 193. https://doi.org/10.1002/jhet.5570210138
  2. Zhang, D.; Ji, X.; Gao, R.; Wang, H.; Meng, S.; Zhong, Z.; Li, Y.; Jiang, J.; Li, Z. Acta Phar. Sin. B 2012, 2, 575. https://doi.org/10.1016/j.apsb.2012.10.005
  3. Choi, E. J.; Lee, J. I.; Kim, G.-H. Int. J. Mol. Med. 2012, 29, 252. https://doi.org/10.3892/ijmm.2011.834
  4. Wang, H.-K.; Bastow, K. F.; Cosentino, L. M.; Lee, K. H. J. Med. Chem. 1996, 39, 1975. https://doi.org/10.1021/jm960008c
  5. Jang, E. J.; Seok, Y. M.; Lee, J. I.; Cho, H. M.; Sohn, U. D.; Kim, I. K. Naunyn-Schmiedeberg's Arch. Pharmacol. 2013, 386, 339. https://doi.org/10.1007/s00210-012-0818-z
  6. (a) Dong, J.; Zhang, Q.; Meng, Q.; Wang, Z.; Li, S.; Cui, J. Mini-Reviews Med. Chem. 2018, 18, 1714. https://doi.org/10.2174/1389557518666180515145633
  7. (b) Sosnovskikh, V. Y. Russ. Chem. Rev. 2018, 87, 49. https://doi.org/10.1070/RCR4756
  8. (a) Nakazumi, H.; Watanabe, S.; Kitaguchi, T.; Kitao, T. Bull. Chem. Soc. Jpn. 1990, 63, 847. https://doi.org/10.1246/bcsj.63.847
  9. (b) Sabatini, S.; Gosetto, F.; Manfroni, G.; Tabarrini, O.; Kaatz, G. W.; Patel, D.; Cecchetti, V. J. Med. Chem. 2011, 54, 5722. https://doi.org/10.1021/jm200370y
  10. (a) French, K. L.; Angel, A. J.; Williams, A. R.; Hurst, D. R.; Beam, C. F. J. Heterocyclic Chem. 1998, 35, 45. https://doi.org/10.1002/jhet.5570350109
  11. (b) Metz, C. R.; Knight, J. D.; Pastine, S. J.; Pennington, W. T.; Beam, C. F. J. Chem. Crystallogr. 2010, 40, 536. https://doi.org/10.1007/s10870-010-9692-z
  12. Vijay, T. A. J.; Nandeesh, K. N.; Raghavendra, G. M.; Rangappa, K. S.; Mantelingu, K. Tetrahedron Lett. 2013, 54, 6533. https://doi.org/10.1016/j.tetlet.2013.09.094
  13. Lee, J. I. Bull. Kor. Chem. Soc. 2009, 30, 710. https://doi.org/10.5012/bkcs.2009.30.3.710
  14. Vargas, E.; Echeverri, F.; Velez, I. D.; Robledo, S. M.; Quinones, W. Molecules 2017, 22, 2041. https://doi.org/10.3390/molecules22122041
  15. (a) Kumar, P.; Rao, A. T.; Pandey, B. J. Chem. Soc. Chem. Commun. 1992, 1580.
  16. (b) Kumar, P.; Bodas, M. S. Tetrahedron 2001, 57, 9755. https://doi.org/10.1016/S0040-4020(01)00977-2
  17. Kobayashi, K.; Kobayashi, A.; Ezaki, K. Heterocycles 2012, 85, 1997. https://doi.org/10.3987/COM-12-12508
  18. Sangeetha, S.; Sekar, G. Org. Lett. 2019, 21, 75. https://doi.org/10.1021/acs.orglett.8b03508
  19. Wang, D.; Sun, P.; Jia, P.; Peng, J.; Yue, Y.; Chen, C. Synthesis 2017, 49, 4309. https://doi.org/10.1055/s-0036-1588466
  20. (a) Fuchs, F. C.; Eller, G. A.; Holzer, W. Molecules 2009, 14, 3814. https://doi.org/10.3390/molecules14093814
  21. (b) Lee, J. I. Bull. Kor. Chem. Soc. 2012, 33, 1375. https://doi.org/10.5012/bkcs.2012.33.4.1375
  22. (c) Lee, J. I.; Choi, J. S. J. Kor. Chem. Soc. 2015, 59, 253. https://doi.org/10.5012/jkcs.2015.59.3.253
  23. (a) Willy, B.; Muller, T. J. J. Synlett 2009, 2009, 1255.
  24. (b) Willy, B.; Frank, W.; Muller, T. J. J. Org. Biomol. Chem. 2010, 8, 90. https://doi.org/10.1039/b917627f
  25. Yang, X.; Li, S.; Liu, H.; Jiang, Y.; Fu, H. RSC Adv. 2012, 2, 6549. https://doi.org/10.1039/c2ra20897k
  26. Kim, H. Y.; Song, E.; Oh, K. Org. Lett. 2017, 19, 312. https://doi.org/10.1021/acs.orglett.6b03348
  27. Shen, C.; Spannenberg, A.; Wu, X. F. Angew. Chem. Int. Ed. 2016, 55, 5067. https://doi.org/10.1002/anie.201600953
  28. (a) Taylor, A. W.; Dean, D. K. Tetrahedron Lett. 1988, 29, 1845. https://doi.org/10.1016/S0040-4039(00)82060-2
  29. (b) Kataoka, T.; Watanabe, S.; Mori, E.; Kadomoto, R.; Tanimura, S.; Kohno, M. Bioorg. Med. Chem. 2004, 12, 2397. https://doi.org/10.1016/j.bmc.2004.02.002
  30. Lee, J. I. J. Kor. Chem. Soc. 2019, 63, 398. https://doi.org/10.5012/JKCS.2019.63.5.398

피인용 문헌

  1. Novel Synthesis of Thioflavones and Their Pyridyl Analogs from 2-Mercaptobenzoic(nicotinic) Acid vol.65, pp.2, 2020, https://doi.org/10.5012/jkcs.2021.65.2.166