Domino aryne precursor: Efficient construction of 2,4-disubstituted benzothiazoles

Journal of the American Chemical Society

Volumn 137, Issue 17, 2015, Pages 5670-5673

  Shi, Jiarong ^a   Qiu, Dachuan ^a   Wang, Juan ^a   Xu, Hai ^a   Li, Yang ^a  

^a CHONGQING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

BENZOTHIAZOLES; C-C BONDS; EFFICIENT CONSTRUCTION;

CHEMICAL REACTIONS;

ARYNE; BENZOTHIAZOLE DERIVATIVE; NUCLEOPHILE; ORGANIC COMPOUND; REAGENT; THIOBENZAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BAEYER VILLIGER REACTION; BECKMANN REARRANGEMENT; CHEMICAL BOND; CHEMICAL REACTION; CRYSTAL STRUCTURE; DRUG SYNTHESIS; NUCLEOPHILICITY;

EID: 84928975226     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02566     Document Type: Article

References (47)

1. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502-528
2. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730
3. Sanz, R. Org. Prep. Proc. Int. 2008, 40, 215-291
4. Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3766-3778
5. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550-3577
6. Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140-3152
7. Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem. 2013, 11, 191-218
8. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211-1214
9. Ikawa, T.; Takagi, A.; Kurita, Y.; Saito, K.; Azechi, K.; Egi, M.; Kakiguchi, K.; Kita, Y.; Akai, S. Angew. Chem., Int. Ed. 2010, 49, 5563-5566
10. Medina, J. M.; Mackey, J. L.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 15798-15805
11. Du, C.-J. F.; Hart, H.; Ng, K.-K. D. J. Org. Chem. 1986, 51, 3162-3165
12. Du, C.-J. F.; Hart, H. J. Org. Chem. 1987, 52, 4311-4314
13. Kirkham, J. D.; Delaney, P. M.; Ellames, G. J.; Row, E. C.; Harrity, J. P. A. Chem. Commun. 2010, 46, 5154-5156
14. Michel, B.; Greaney, M. F. Org. Lett. 2014, 16, 2684-2687
15. Rodríguez-Lojo, D.; Cobas, A.; Peña, D.; Pérez, D.; Guitián, E. Org. Lett. 2012, 14, 1363-1365
16. Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955-2958
17. Yoshida, H.; Yoshida, R.; Takaki, K. Angew. Chem., Int. Ed. 2013, 52, 8629-8632
18. Hendrick, C. E.; McDonald, S. L.; Wang, Q. Org. Lett. 2013, 15, 3444-3447
19. Hall, C.; Henderson, J. L.; Ernouf, G.; Greaney, M. F. Chem. Commun. 2013, 49, 7602-7604
20. Goetz, A. E.; Garg, N. K. Nat. Chem. 2013, 5, 54-60
21. Yoshida, S.; Uchida, K.; Igawa, K.; Tomooka, K.; Hosoya, T. Chem. Commun. 2014, 50, 15059-15062
22. Ikawa, T.; Kaneko, H.; Masuda, S.; Ishitsubo, E.; Tokiwa, H.; Akai, S. Org. Biomol. Chem. 2014, 13, 520-526
23. Yoshida, H.; Terayama, T.; Ohshita, J.; Kunai, A. Chem. Commun. 2004, 1980-1981
24. Lin, W. W.; Sapountzis, I.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 4258-4261
25. Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 4273-4275
26. Biswas, K.; Greaney, M. F. Org. Lett. 2011, 13, 4946-4949
27. Pandya, V. G.; Mhaske, S. B. Org. Lett. 2014, 16, 3836-3839
28. Yoshida, H.; Shirakawa, E.; Honda, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2002, 41, 3247-3249
29. Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673-4675
30. Liu, Z.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 13112-13113
31. Yoshida, H.; Morishita, T.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2007, 9, 3367-3370
32. Okuma, K.; Matsunaga, N.; Nagahora, N.; Shioji, K.; Yokomori, Y. Chem. Commun. 2011, 47, 5822-5824
33. García-López, J.-A.; Cetin, M.; Greaney, M. F. Angew. Chem., Int. Ed. 2015, 54, 2156-2159
34. Pintori, D. G.; Greaney, M. F. Org. Lett. 2010, 12, 168-171
35. Fang, Y.; Rogness, D. C.; Larock, R. C.; Shi, F. J. Org. Chem. 2012, 77, 6262-6270
36. Saito, N.; Nakamura, K.-i.; Shibano, S.; Ide, S.; Minami, M.; Sato, Y. Org. Lett. 2013, 15, 386-389
37. Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340-5341
38. Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Commun. 2005, 3292-3294
39. Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2005, 46, 6729-6731
40. Liu, Y.-L.; Liang, Y.; Pi, S.-F.; Li, J.-H. J. Org. Chem. 2009, 74, 5691-5694
41. Tadross, P. M.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1612-1614
42. Facchinetti, V.; Reis, R. d. R.; Gomes, C. R. B.; Vasconcelos, T. R. A. Mini-Rev. Org. Chem. 2012, 9, 44-53
43. Prajapati, N. P.; Vekariya, R. H.; Borad, M. A.; Patel, H. D. RSC Adv. 2014, 4, 60176-60208
44. Przytulinska, M. K.; Penning, T. D.; Tong, Y. WO 2010083199A1, 2010.
45. Vu, C. B. WO 2010019606A1, 2010.
46. Barlaam, B.; Bernstein, P.; Dantzman, C.; Warwick, P. WO 2002051821A1, 2002.
47. Keri, R. S.; Patil, M. R.; Patil, S. A.; Budagumpi, S. Eur. J. Med. Chem. 2015, 89, 207-251