Synthesis of 2-benzylthio-5-phenyl-3,4-disubstituted thiophenes by intramolecular condensation of α-oxo ketene dibenzylthioacetals

Chinese Journal of Chemistry

Volumn 20, Issue 12, 2002, Pages 1591-1597

  Wang, Mang ^a,b   Ai, Lin ^a,c   Zhang, Ji Yu ^a   Liu, Qun ^a   Gao, Lian Xun ^b  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^c BEIJING NORMAL UNIVERSITY   (China)

Author keywords

Intramolecular aldol type condensation; Multisubstituted thiophenes; oxo ketene dibenzylthioacetals; oxo ketene dithioacetals

Indexed keywords

EID: 1342272349     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20020201223     Document Type: Article

References (31)

1. (a) Dieter, R. K. Tetrahedron 1986, 42, 3029.
2. (b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
3. (c) Liu, Q.; Yang, Z. Y. Chin. J. Org. Chem. 1992, 12, 225 (in Chinese).
4. (d) Wang, M.; Liu, Q.; Zhao, M. X.; Li, J. X. Northeast Normal Univ. Xuebao 1999, 4, 48 (in Chinese).
5. (a) Kishore, K.; Reddy, K. R.; Suresh, J. R.; Ila, H.; Junjappa, H. Tetrahedron 1999, 55, 7645.
6. (b) Barun, O.; Ila, H.; Junjappa, H.; Singh, O. M. J. Org. Chem. 2000, 65, 1583.
7. (c) Suresh, J. R.; Barun, O.; Ila, H.; Junjappa, H. Tetrahedron 2000, 56, 8153.
8. (d) Suresh, J. R.; Kumar, U. K. S.; Ila, H.; Junjappa, H. Tetrahedron 2001, 57, 781.
9. (e) Ila, H.; Junjappa, H.; Barun, O. J. Organomet. Chem. 2001, 624, 34.
10. (f) Mohanta, P. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2001, 66, 1503.
11. (a) Gill, S.; Kocienski, P.; Kohler, A.; Pontiroli, A.; Liu, Q. J. Chem. Soc., Chem. Commun. 1996, 1743.
12. (b) Kocienski, P. J.; Pontiroli, A.; Liu, Q. J. Chem. Soc., Perkin Trans. 1 2001, 2356.
13. (c) Liu, Q.; Xu, B. L.; Yang, Z. Y.; Zhao, H. W. Chem. J. Chin. Univ. 1995, 16, 1047 (in Chinese).
14. (d) Liu, Q.; Zhao, H. W.; Yang, Z. Y.; Xu, B. L. Chem. J. Chin. Univ. 1996, 17, 73 (in Chinese).
15. (e) Liu, Q.; Zhu, Z. M.; Yang, Z. Y.; Hu, Y. L.; Jing, F. Y.; Xiao, Y. W. Chem. J. Chin. Univ. 1993, 14, 1538 (in Chinese).
16. (f) Yang, Z. Y.; Wang, Z. L.; Liu, Q. Chem. J. Chin. Univ. 1994, 15, 697 (in Chinese).
17. (a) Blicke, F. F. In The Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Ed.: Hartough, H. D., Inteiscience Publishers, ING., New York, 1952, Chapter 2.
18. (b) Gronowitz, S. In The Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Vol. 44, Part 3, Ed.: Gronowitz, S. J., Wiley and Sons, New York, 1991, Chapter 2.
19. Shu, C. K.; Myrna, L. H.; Ho, C. T. J. Agric. Food Chem. 1986, 34, 344.
20. Roncali, J. Chem. Rev. 1992, 92, 711.
21. Nalwa, H. S. Adv. Mater. 1993, 5, 341.
22. (a) Bartolo, G.; Giuseppe, S.; Alessia, F. Org. Lett. 2000, 2, 351.
23. (b) Fazio, A.; Gabriele, B.; Salerno, G.; Destri, S. Tetrahedron 1999, 55, 485.
24. (c) Ong, C. W.; Chen, C. M.; Wang, L. F.; Shieh, P. C. Tetrahedron Lett. 1998, 39, 9191.
25. (d) Stephensen, H.; Zaragoza, F. J. Org. Chem. 1997, 62, 6096.
26. (e) Apparao, S.; Ila, H.; Junjappa, H. J. Chem. Soc., Perkin Trans. 1 1983, 2837.
27. Wang, M.; Liu, Q.; Zhao, M. X.; Wang, L. M. Chin. Chem. Lett. 2000, 11, 3.
28. Marino, J. P.; Kostusyk, J. L. Tetrahedron Lett. 1979, 20, 2489, 2493.
29. (a) Relyea, D. I.; Hubband, W. L.; Grahame, R. E. US 4 174 405, 1979 [Chem. Abstr. 1980, 92, 94229].
30. (b) Unirooyal, I. Israeli 47 687, 1979 [Chem. Abstr. 1980, 92, 198260].
31. Fan, N. T. In Notebook of Organic Synthesis (in Chinese), Peking University of Science and Technology, Beijing, 1992, p. 758, p. 879, p. 795.