Practical synthesis of tetrasubstituted thiophenes for use in compound libraries

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5471-5474

  McKibben, Bryan P ^a   Cartwright, Craig H ^a   Castelhano, Arlindo L ^a  

^a Cadus Pharmaceutical Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIOPHENE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0033165866     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01108-9     Document Type: Article

References (24)

1. For general reviews of multicomponent reactions see: (a) Posner, G. Chem. Rev. 1986, 86, 831.
2. (b) Ugi, I.; Lohberger, R.K. In Comprehensive Organic Synthesis, Vol. 2 (Eds. Trost, B.; Fleming, I.), Pergamon, New York, 1991, pp. 1083-1109. Ugi, I.; Domling, W.H. Endeavor, 1994, 18, 115.
3. (b) Ugi, I.; Lohberger, R.K. In Comprehensive Organic Synthesis, Vol. 2 (Eds. Trost, B.; Fleming, I.), Pergamon, NewYork, 1991, pp. 1083-1109. Ugi, I.; Domling, W.H. Endeavor, 1994, 18, 115.
4. For a review of combinatorial synthesis, including multicomponent reactions see: Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288.
5. (a) Hanusch-Kompa, C.; Ugi, I. Tetrahedron Lett. 1998, 39, 2725.
6. (b) Armstrong, R.; Brown, D.; Keating, T.; Tempest, P. In Combinatorial Chemistry Synthesis and Applications; (Eds. Wilson, S.; Czarnik, A.), John Wiley and Sons, New York, 1997, p. 153.
7. (c)Short, K.; Ching, B.; Mjalli, A. Tetrahedron 1997, 53, 6653.
8. (d) Armstrong, R.; Combs, A.; Tempest, P.; Brown, S.; Keating, T. Acc. Chem. Res. 1996, 29, 123.
9. (e) Keating, T.; Armstrong, R. J. Am. Chem. Soc. 1996, 118, 2574.
10. (f) Strocker, A.; Keating, T.; Tempest, P.; Armstrong, R Tetrahedron Lett. 1996, 37, 1149.
11. (g) Cao, X.; Moran, E.; Siev, D.; Lio, A.; Ohasi, C.; Mjalli, A. Bioorg. Med. Chem. Lett. 1995, 5, 2953. Ugi, I. Isonitrile Chemistry, Academic Press, London, 1971.
12. (g) Cao, X.; Moran, E.; Siev, D.; Lio, A.; Ohasi, C.;Mjalli, A. Bioorg. Med. Chem. Lett. 1995, 5, 2953. Ugi, I. Isonitrile Chemistry, Academic Press, London, 1971.
13. (a) Hu, E.; Sidler, D.; Dolling, U. J. Org Chem. 1998, 63, 3454.
14. (b) Wipf, P.; Cunnigham, A. Tetrahedron Lett. 1996, 36, 7819.
15. (c) Blackburn, C. Tetrahedron Lett. 1998, 5469.
16. (d) Richter H.; Jung, G. Tetrahedron Lett. 1998, 2729.
17. (a) Gewald, K. Chem. Ber. 1965, 98, 3571.
18. (b) Gewald, K.; Schinke, E.; Bottcher, H. Chem. Ber. 1966, 99, 94.
19. (C) Sampson, N.; Bartlett, P. J. Org. Chem. 1991, 56, 7179.
20. We speculate that the more bulky esters may hinder aldol side reactions leading to oligomerization.
21. For functionalization of a -methyl substituent on a similar thiophene nucleus see: (a) Furuya, S. et al, WO 95/28405A (Takeda Chemical Industries Ltd.), 1995.
22. (b) Furuya, S. et al, US 5,744,479A (Takeda Chemical Industries Ltd.), 1998.
23. 1 receptor antagonists see: Whitten, J.; Xie, Y.; Erickson, P.; Webb, T.; DeSouza, E.; Grigoriadis, D. McCarthy, J. J. Med. Chem. 1996, 39, 4354.
24. ++1).