Copper-catalyzed thiolation annulations of 1,4-dihalides with sulfides leading to 2-trifluoromethyl benzothiophenes and benzothiazoles

Journal of Organic Chemistry

Volumn 75, Issue 20, 2010, Pages 7037-7040

  Li, Chun Lin ^a   Zhang, Xing Guo ^a,b   Tang, Ri Yuan ^a   Zhong, Ping ^a   Li, Jin Heng ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLES; DIHALIDES; GOOD YIELD; THIOLATION; TRIFLUOROMETHYL;

CATALYSIS; CHLORINE COMPOUNDS; SODIUM;

THIOPHENE;

2 (TRIFLUOROMETHYL)BENZO[D]THIAZOLE; 2 TRIFLUOROMETHYLBENZOTHIOPHENE DERIVATIVE; 6 METHYL 2 (TRIFLUOROMETHYL)BENZO[B]THIOPHENE; BENZOTHIAZOLE DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; COPPER; HALIDE; SULFIDE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; SYNTHESIS; THIOLATION;

BENZOTHIAZOLES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; SULFIDES; THIOPHENES;

EID: 77957921049     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101675f     Document Type: Article

References (40)

1. Guo, H. F.; Shao, H. Y.; Yang, Z. Y.; Xue, S. T.; Li, X.; Liu, Z. Y.; He, X. B.; Jiang, J. D.; Zhang, Y. Q.; Si, S. Y.; Li, Z. R. J. Med. Chem. 2010, 53, 1819
2. Raga, M.; Palacin, C.; Castello, J. M.; Ortiz, J. A.; Cuberes, M. R.; Moreno-Manas, M. Eur. J. Med. Chem. 1986, 21, 329
3. Wang, X.; Sarris, K.; Kage, K.; Zhang, D.; Brown, S. P.; Kolasa, T.; Surowy, C.; Kouhen, O. F. E.; Muchmore, S. W.; Brioni, J. D.; Stewart, A. O. J. Med. Chem. 2009, 52, 170
4. Van Zandt, M. C.; Jones, M. L.; Gunn, D. E.; Geraci, L. S.; Jones, J. H.; Sawicki, D. R.; Sredy, J.; Jacot, J. L.; DiCioccio, A. T.; Petrove, T.; Mitschler, A.; Podjarny, A. D. J. Med. Chem. 2005, 48, 3141
5. Mortimer, C. G.; Wells, G.; Crochard, J. P.; Stone, E. L.; Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. J. Med. Chem. 2006, 49, 179
6. Aiello, S.; Wells, G.; Stone, E. L.; Kadri, H.; Bazzi, R.; Bell, D. R.; Stevens, M. F. G.; Matthews, C. S.; Bradshaw, T. D.; Westwell, A. D. J. Med. Chem. 2008, 51, 5135
7. Qin, Z.; Kasrati, I.; Chandrasena, R. E. P.; Liu, H.; Yao, P.; Petukhov, P. A.; Bolton, J. L.; Thatcher, G. R. J. J. Med. Chem. 2007, 50, 2682
8. Jones, C. D.; Jevnikar, M. G.; Pike, A. J.; Peters, M. K.; Black, L. J.; Thompson, A. R.; Falcone, J. F.; Clemens, J. A. J. Med. Chem. 1984, 27, 1057
9. Guinchard, X.; Denis, J. N. J. Org. Chem. 2008, 73, 2028
10. Hsiao, C. N.; Kolasa, T. Tetrahedron Lett. 1992, 33, 2629
11. Mylari, B. L.; Larson, E. R.; Beyer, T. A.; Zembrowski, W. J.; Aldinger, C. E.; Dee, M. F.; Siegel, T. W.; Singleton, D. H. J. Med. Chem. 1991, 34, 108
12. For reviews, see: Smart, B. E. J. Fluorine Chem. 2001, 109, 3
13. Maienfisch, P.; Hall, R. G. Chimia 2004, 58, 93
14. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
15. Organofluorine Chemistry; Uneyama, K., Ed.; Blackwell Publishing: Oxford, UK, 2006.
16. Organofluorine Compounds: Chemistry and Application; Hiyama, T., Ed.; Springer: New York, 2000.
17. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Kirsch, P., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
18. Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214
19. Sawada, H.; Nasaharu, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1990, 46, 423
20. Akiyama, T.; Kato, K.; Kajitani, M.; Sakaguchi, Y.; Nakamura, J.; Hayashi, H.; Sugimori, A. Bull. Chem. Soc. Jpn. 1988, 61, 3531
21. Matthews, D. P.; Whitten, J. P.; McCartthy, J. R. Tetrahedron Lett. 1986, 27, 4861
22. Ge, F.; Wang, Z.; Wan, W.; Lu, W.; Hao, J. Tetrahedron Lett. 2007, 48, 325
23. Li, Z.; Yang, Q.; Qian, X. Bioorg. Med. Chem. 2005, 13, 4864
24. Zhu, J.; Chen, Z.; Xie, H.; Li, S.; Wu, Y. Org. Lett. 2010, 12, 2434
25. You, W.; Yan, X.; Liao, Q.; Xi, C. Org. Lett. 2010, 12, 3930
26. Fanta, P. E. Chem. Rev. 1946, 38, 139
27. Fanta, P. E. Chem. Rev. 1964, 64, 613
28. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359
29. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428
30. Liang, Y.; Li, J.-H. Chin. J. Org. Chem. 2005, 25, 147
31. Frlan, R.; Kikelj, D. Synthesis 2006, 2271
32. Chemler, S. R.; Fuller, P. H. Chem. Soc. Rev. 2007, 36, 1153
33. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096
34. Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133
35. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954
36. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450
37. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
38. Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew. Chem., Int. Ed. 2009, 48, 4222
39. Chen, M.-W.; Zhang, X.-G.; Zhong, P.; Hu, M.-L. Synthesis 2009, 1431
40. Dong, S.-X.; Zhang, X.-G.; Liu, Q.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Synthesis 2010, 1521