Synthesis of 2-mercaptobenzothiazoles via DBU-promoted tandem reaction of o-haloanilines and carbon disulfide

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3202-3205

  Wang, Fei ^a   Cai, Shangjun ^a   Wang, Zhipeng ^a   Xi, Chanjuan ^b  

^a Tsinghua University   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 MERCAPTOBENZOTHIAZOLE; ANILINE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; CARBON DISULFIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ANILINE COMPOUNDS; BENZOTHIAZOLES; CARBON DISULFIDE; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE;

EID: 79958858521     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2011105     Document Type: Article

References (58)

1. Wilde, R. G.; Billheimer, J. T.; Germain, S. J.; Gillies, P. J.; Higley, C. A.; Kezar, H. S., III; Maduskuie, T. P.; Shimshick, E. S.; Wexler, R. R. Bioorg. Med. Chem. Lett. 1995, 5, 167
2. Chen, W.; Huang, Y.; Gundala, S. R.; Yang, H.; Li, M.; Tai, P. C.; Wang, B. Bioorg. Med. Chem. 2010, 18, 1617
3. Easmon, J.; Heinisch, G.; Hofmann, J.; Langer, T.; Grunicke, H.; Fink, J.; Pürstinger, G. Eur. J. Med. Chem. 1997, 32, 397
4. Zhang, L.; Fan, J.; Vu, K.; Hong, K.; Le Brazidec, J.-Y.; Shi, J.; Biamonte, M.; Busch, D. J.; Lough, R. E.; Grecko, R.; Ran, Y.; Sensintaffar, J. L.; Kamal, A.; Lundgren, K.; Burrows, F. J.; Mansfield, R.; Timony, G. A.; Ulm, E. H.; Kasibhatla, S. R.; Boehm, M. F. J. Med. Chem. 2006, 40, 5352
5. Dumas, J.; Brittelli, D.; Chen, J.; Dixon, B.; Hatoum-Mokdad, H.; Konig, G.; Sibley, R.; Witowsky, J.; Wong, S. Bioorg. Med. Chem. Lett. 1999, 9, 2531
6. Jiang, L.-L.; Tan, Y.; Zhu, X.-L.; Wang, Z.-F.; Zuo, Y.; Chen, Q.; Xi, Z.; Yang, G.-F. J. Agric. Food Chem. 2010, 58, 2643
7. Cressier, D.; Prouillac, C.; Hernandez, P.; Amourette, C.; Diserbo, M.; Lion, C.; Rima, G. Bioorg. Med. Chem. 2009, 17, 5275
8. Patt, H. M.; Tyree, E. B.; Straube, R. L.; Smith, D. E. Science 1949, 110, 213
9. Foye, W. O. Radioprotective Drugs. In Burger's Medicinal Chemistry, 4 th ed.; Wolff, M. E., Ed.; Wiley: New York, 1981; pp 11-45.
10. Franchini, C.; Muraglia, M.; Corbo, F.; Florio, M. A.; Mola, A. D.; Rosato, A.; Matucci, R.; Nesi, M.; Bambeke, F.; Vitali, C. Arch. Pharm. Chem. Life Sci. 2009, 342, 605
11. Katkova, M. A.; Borisov, A. V.; Fukin, G. K.; Baranov, E. V.; Averyushkin, A. S.; Vitukhnovsky, A. G.; Bochkarev, M. N. Inorg. Chim. Acta 2006, 359, 4289
12. Mishra, L.; Vilaplana, R.; Singh, V. K.; Yadaw, A. K.; González-Vilchez, F. J. Inorg. Biochem. 2001, 86, 581
13. Teppema, J.; Sebrell, L. B. J. Am. Chem. Soc. 1927, 49, 1779
14. Teppema, J.; Sebrell, L. B. J. Am. Chem. Soc. 1927, 49, 1748
15. Sebrell, L. B.; Boord, C. E. J. Am. Chem. Soc. 1923, 45, 2390
16. Ballabeni, M.; Ballini, R.; Bigi, F.; Maggi, R.; Parrini, M.; Predieri, G.; Sartori, G. J. Org. Chem. 1999, 64, 1029
17. Zhu, N.; Zhang, F.; Liu, G. J. Comb. Chem. 2010, 12, 531
18. Huang, W.; Tan, Y.; Ding, M.-W.; Yang, G.-F. Synth. Commun. 2007, 37, 369
19. Zhu, L.; Zhang, M.; Dai, M. J. Heterocyclic Chem. 2005, 42, 727
20. Harizi, A.; Romdhane, A.; Mighri, Z. Tetrahedron Lett. 2000, 41, 5833
21. Karlsson, H. J.; Lincoln, P.; Westman, G. Bioorg. Med. Chem. 2003, 11, 1035
22. Zhu, L.; Zhang, M. J. Org. Chem. 2004, 69, 7371
23. Chaudhuri, N. C. Synth. Commun. 1996, 26, 3783
24. Singh, B.; Pennock, P. O.; Lesher, G. Y.; Bacon, E. R.; Page, D. F. Heterocycles 1993, 36, 133
25. Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew. Chem., Int. Ed. 2011, 50, 1118
26. For recent one-pot reactions based on C-N bond formation, see: Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed. 2007, 46, 2598
27. Zheng, N.; Buchwald, S. L. Org. Lett. 2007, 9, 4749
28. Zou, B.; Yuan, Q.; Ma, D. Org. Lett. 2007, 9, 4291
29. Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Org. Lett. 2008, 10, 625
30. Martín, R.; Rivero, M. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 7079
31. Viña, D.; del Olmo, E.; López-Pérez, J. L.; Feliciano, A. S. Org. Lett. 2007, 9, 525
32. Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843
33. Chen, Y.; Xie, X.; Ma, D. J. Org. Chem. 2007, 72, 9329
34. Liu, F.; Ma, D. J. Org. Chem. 2007, 72, 4844
35. Jones, C. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2007, 72, 7968
36. Tanimori, S.; Ura, H.; Kirihata, M. Eur. J. Org. Chem. 2007, 3977
37. Martin, R.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 5521
38. Saha, P.; Ramana, T.; Purkait, N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719
39. Lv, X.; Bao, W. J. Org. Chem. 2009, 74, 5618
40. Hu, T.; Li, C. Org. Lett. 2005, 7, 2035
41. Wang, Y.; Liao, Q.; Xi, C. Org. Lett. 2010, 12, 2951
42. Liao, Q.; Zhang, L.; Wang, F.; Li, S.; Xi, C. Eur. J. Org. Chem. 2010, 5426
43. Liao, Q.; Zhang, L.; Li, S.; Xi., C. Org. Lett. 2010, 13, 228
44. For recent one-pot reactions based on C-O bond formation, see: Lu, B.; Wang, B.; Zhang, Y.; Ma, D. J. Org. Chem. 2007, 72, 5337
45. Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978
46. Viirre, R. D.; Evindar, G.; Batey, R. A. J. Org. Chem. 2008, 73, 3452
47. For recent reactions based on C-S bond formation, see: Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587
48. Shen, G.; Lv, X.; Bao, W. Eur. J. Org. Chem. 2009, 5897
49. Guo, Y.-J.; Tang, R.-Y.; Zhao, P.; Li, J.-H. Tetrahedron Lett. 2010, 51, 649
50. Murru, S.; Ghosh, H.; Sahoo, S. K.; Patel, B. K. Org. Lett. 2009, 11, 4254
51. Lv, X.; Liu, Y.; Qian, W.; Bao, W. Adv. Synth. Catal. 2008, 350, 2507
52. Zhao, Q.; Li, L.; Fang, Y.; Sun, D.; Li, C. J. Org. Chem. 2009, 74, 459
53. Bryan, C. S.; Braunger, J. A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 7064
54. You, W.; Yan, X.; Liao, Q.; Xi, C. Org. Lett. 2010, 12, 3930
55. Wang, F.; Zhao, P.; Xi, C. Tetrahedron Lett. 2011, 52, 231
56. Wang, F.; Cai, S.; Liao, Q.; Xi, C. J. Org. Chem. 2011, 76, 3174
57. Wang, F.; Wang, Y.; Cai, L.; Miao, Z.; Chen, R. Adv. Synth. Catal. 2008, 350, 2733
58. Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonehara, M.; Hiroya, K.; Sakamoto, T. Org. Lett. 2006, 8, 5517