Electrophilic cyclization of 4-thio-but-2-yn-1-ols via 1,2-migration of the thio group: efficient synthesis of 2,4-dihalo-3-thio-substituted furans

Tetrahedron Letters

Volumn 49, Issue 2, 2008, Pages 226-228

  Zhou, Hongwei ^a   Yao, Jinzhong ^a   Liu, Guoliang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

1,2 Migration of thio group; 2,4 Dihalo 3 thio furan; 4 Thio but 2 yn 1 ol; Electrophilic cyclization

Indexed keywords

2,4 DIHALO 3 THIOFURAN DERIVATIVE; 4 THIOBUT 2 YN 1 OL; FURAN DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 36849058631     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.092     Document Type: Article

References (30)

1. For a review, please see:. Sromek A.W., and Gevorgyan V. Top. Curr. Chem. 274 (2007) 77
2. Peng L., Zhang X., Ma M., and Wang J. Angew. Chem., Int. Ed. 46 (2007) 1905
3. Peng L., Zhang X., Ma J., Zhong Z., and Wang J. Org. Lett. 9 (2007) 1445
4. Yue D., and Larock R.C. Org. Lett. 6 (2004) 1037
5. Sniady A., Wheeler K.A., and Dembinski R. Org. Lett. 7 (2005) 1769
6. Peng A., and Ding Y. Org. Lett. 6 (2004) 1119
7. Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 1432
8. Yue D., and Larock R.C. J. Org. Chem. 67 (2002) 1905
9. Hessian K.O., and Flynn B.L. Org. Lett. 5 (2003) 4377
10. Yao T., Campo M.A., and Larock R.C. Org. Lett. 6 (2004) 2677
11. Yue D., Della Ca.N., and Larock R.C. Org. Lett. 6 (2004) 1581
12. Barluenga J., Trincado M., Marco-Arias M., Ballesteros A., Rubio E., and Gonzalez J.M. Chem. Commun. (2005) 2008
13. Liu Y., Song F., and Cong L. J. Org. Chem. 70 (2005) 6999
14. Nie J., Zhu H., Cui H., Hua M., and Ma J.A. J. Org. Lett. 9 (2007) 3053
15. Worlikar S.A., Kesharwani T., Yao T., and Larock R.C. J. Org. Chem. 72 (2007) 1347
16. Pedrosa R., Andres C., Mendiguchia P., and Nieto J. J. Org. Chem. 71 (2006) 8854
17. Yue D., Yao T., and Larock R.C. J. Org. Chem. 71 (2006) 62
18. Zhang X., Sarkar S., and Larock R.C. J. Org. Chem. 71 (2006) 236
19. Yue D., Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 10292
20. Waldo J.P., and Larock R.C. Org. Lett. 7 (2005) 5203
21. Peng L., Zhang X., Zhang S., and Wang J. J. Org. Chem. 72 (2007) 1192
22. Xu F., Shi W., and Wang J. J. Org. Chem. 70 (2005) 4191
23. Fox D.J., House D., and Warren S. Angew. Chem., Int. Ed. 41 (2002) 2462
24. House D., and Warren S. Phosphorus Sulfur Silicon Relat. Elem. (1999) 153
25. Baldwin I.C., Briner P., Eastgate M.D., Fox D.G., and Warren S. Org. Lett. 4 (2002) 4381
26. Caggiano L., Davies J., Fox D.J., Moody D.C., and Warren S. Chem. Commun. (2003) 1648
27. Caggiano L., Fox D.J., and Warren S. Chem. Commun. (2002) 2528
28. Gevorgyan V., Kel'in A.V., and Kim J.T. Angew. Chem., Int. Ed. 42 (2003) 98
29. Hamel P. Tetrahedron Lett. 38 (1997) 8473
30. 2OS: C, 35.68; H, 1.68; found: C, 36.02; H, 1.99.