Synthesis of N-benzothiazol-2-yl-amides by a copper-catalyzed intramolecular cyclization process

Tetrahedron Letters

Volumn 49, Issue 3, 2008, Pages 467-470

  Wang, Junke ^a   Peng, Feng ^a   Jiang, Ju li ^a   Lu, Zhi jin ^a   Wang, Le yong ^a   Bai, Junfeng ^b   Pan, Yi ^a,b  

^a NANJING UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

Benzothiazol 2 yl amide; Copper; Intramolecular cyclization; Thiourea

Indexed keywords

1 ACYL 3 (2 BROMOPHENYL)THIOUREA; AMIDE; BENZOTHIAZOLE DERIVATIVE; COPPER; N (4,5 DIHYDROOXAZOL 2 YL)BENZAMIDE; N BENZOTHIAZOL 2 YL AMIDE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 37249037663     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.100     Document Type: Article

References (50)

1. Parlati, F.; Ramesh, U. V.; Singh, Rajinder; P.; Donald G.; Lowe, R.; Look, G. C. PCT Int. Appl. 2005, WO 2005037845.
2. Yoshida M., Hayakawa I., Hayashi N., Agatsuma T., Oda Y., Tanzawa F., Iwasaki S., Koyama K., Furukawa H., Kurakatad S., and Suganob Y. Bioorg & Med Chem Lett 15 (2005) 3328-3332
3. Bailey, T. R.; Pevear, D. C. PCT Int. Appl. 2004, WO 2004078115.
4. Alanine, A.; Flohr, A.; Miller, A. K.; Norcross, R. D.; Riemer, C. PCT Int. Appl. 2001, WO 2001097786.
5. Kerwin, S.; Hurley, L. H.; De Luca, M. R.; Moore, B. M.; PCT Int. Appl. 1997, WO 9748694.
6. Brade A.R., Khadse H.B., and Bobade A.S. Indian Drugs 35 (1998) 554-557
7. Starcevic K., Caleta I., Cincic D., Kaitner B., Kralj M., Ester K., and Karminski-Zamola G. Heterocycles 68 (2006) 2285-2299
8. Armenise D., De Laurentis N., Reho A., Rosato A., and Morlacchi F. J. Heterocycl. Chem. 41 (2004) 771-775
9. Yang L.Z., Wei T.B., and Zhang Y.M.J. Chem. Res. Synop. (2005) 700-701
10. Sedlák M., Hanusek J., Holčapek M., and Štěrba V. J. Phys. Org. Chem. 14 (2001) 187-195
11. Jayanthi G., Muthusamy S., Paramasivam R., Ramakrishnan V.T., Ramasamy N.K., and Ramamurthy P. J. Org. Chem. 62 (1997) 5766-5770
12. For reviews, see:. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428-2439
13. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400-5449
14. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337-2364
15. Deng W., Liu L., and Guo Q.X. Chin. J. Org. Chem. 24 (2004) 150-165
16. Dehli J.R., Legros J., and Bolm C. Chem. Commun. (2005) 973-986
17. For recent copper-catalyzed C-N coupling reactions, see:. Taillefer M., Xia N., and Ouali A. Angew. Chem. 46 (2007) 934-936
18. Chen Y.-J., and Chen H.-H. Org. Lett. 8 (2006) 56095612
19. Altman R.A., and Buchwald S.L. Org. Lett. 8 (2006) 2779-2782
20. Zhang Z., Mao J., Zhu D., Wu F., Chen H., and Wan B. Tetrahedron 62 (2006) 4435-4443
21. Zhang H., Cai Q., and Ma D.W. J. Org. Chem. 70 (2005) 5164-5173
22. Buchwald S.L., Antilla J.C., Baskin J.M., and Barder T.E. J. Org. Chem. 69 (2004) 5578-5587
23. Cristau H.-J., Cellier P., Spindler J.-F., and Taillefer M. Eur. J. Org. Chem. (2004) 695-709
24. Ma D., Cai Q., and Zhang H. Org. Lett. 5 (2003) 2453-2455
25. Kwong F.Y., and Buchwald S.L. Org. Lett. 5 (2003) 793-796
26. Klapars A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 74217428
27. For reviews, see:. Muci A.R., and Buchwald S.L. Top. Curr. Chem. 219 (2002) 131-209
28. Hartwig J.F. In: Negichi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 (2002), Wiley, New York 1051
29. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176-4221
30. Prim D., Campagne J.M., Joseph D., and Andrioletti B. Tetrahedron 58 (2002) 2041-2075
31. Yang B.Y., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125-146
32. Wolfe J.P., Wagaw S., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805-818
33. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046-2067
34. Hartwig J.F. Acc. Chem. Res. 31 (1998) 852-860
35. For selected references, see:. Zhang H., Cai Q., and Ma D. J. Org. Chem. 70 (2005) 5164-5173
36. Choudary B.M., Sridhar C., Kantam M.L., Venkanna G.T., and Sreedhar B. J.Am. Chem. Soc. 127 (2005) 9948-9949
37. Trost B.M., and Stiles D.T. Org. Lett. 7 (2005) 2117-2120
38. Yang T., Lin C., Fu H., Jiang Y., and Zhao Y. Org. Lett. 7 (2005) 4781-4784
39. Hu T., and Li C. Org. Lett. 7 (2005) 2035-2038
40. Fang Y., and Li C. Chem. Commun. (2005) 3574-3576
41. Joyce L.L., Evindar G., and Batey R.A. Chem. Commu. (2004) 446-447
42. Benedí C., Bravo F., Uriz P., Fernández E., Claver C., and Castillón S. Tetrahedron Lett. 44 (2003) 6073-6077
43. Wang X.C., Li Z., Tu Y., and Da Y.X. Synthetic Commun. 32 (2002) 1113-1119
44. Li Z., and Wang X.C. Synthetic Commun. 32 (2002) 3087-3092
45. Jiang J., Duan C., Li Y., Bai J., and Pan Y. Anal. Sci. 20 (2006) x119-x120
46. Jiang J., Duan C., Bai J., and Pan Y. Anal. Sci. 20 (2006) x153-x154
47. 2: C, 63.15; H, 5.30; N, 14.73. Found: C, 63.41; H, 5.38; N, 14.57.
48. Evindar G., and Batey R.A. Org. Lett. 5 (2003) 133-136
49. 2S: C, 45.84; H, 2.45; N, 9.72. Found: C, 46.04; H, 2.49; N, 9.43.
50. Burkhardt J., Hamann K., Forschungsins L., and Pigmente S. Chem. Ber. 100 (1967) 2569-2576