A new thiazole synthesis by cyclocondensation of thioamides and alkynyl(aryl)iodonium reagents

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8004-8005

  Wipf, Peter ^a   Venkatraman, Srikanth ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029802459     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961681c     Document Type: Article

References (26)

1. (a) Wipf, P. Chem. Rev. 1995, 95, 2115.
2. (b) Lewis, J. R. Nat. Prod. Rep. 1995, 135.
3. (c) Wipf, P.; Venkatraman, S. Synlett, in press.
4. Reviews: (a) Liebscher, J. In Heteroarenes III, Houben-Weyl, 4th ed.; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; Part 2, Vol. E8b, pp 1-398. (b) Hassner, A.; Fischer, B. Heterocycles 1993, 35, 1441. (c) Lang-Fugmann, S. In Heteroarenes III, Houben-Weyl, 4th ed.; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1993; Part 1. Vol. E8a, pp 891-1019.
5. Reviews: (a) Liebscher, J. In Heteroarenes III, Houben-Weyl, 4th ed.; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; Part 2, Vol. E8b, pp 1-398. (b) Hassner, A.; Fischer, B. Heterocycles 1993, 35, 1441. (c) Lang-Fugmann, S. In Heteroarenes III, Houben-Weyl, 4th ed.; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1993; Part 1. Vol. E8a, pp 891-1019.
6. Reviews: (a) Liebscher, J. In Heteroarenes III, Houben-Weyl, 4th ed.; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; Part 2, Vol. E8b, pp 1-398. (b) Hassner, A.; Fischer, B. Heterocycles 1993, 35, 1441. (c) Lang-Fugmann, S. In Heteroarenes III, Houben-Weyl, 4th ed.; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1993; Part 1. Vol. E8a, pp 891-1019.
7. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604.
8. (a) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558.
9. (b) Wipf, P.; Venkatraman, S. J. Org. Chem. 1995, 60, 7224.
10. (c) Wipf, P.; Lim, S. Chimia 1996, 50, 157.
11. (d) Wipf, P.; Venkatraman, S. J. Org. Chem. 1996, 61, 6517.
12. Review. Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274.
13. (a) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
14. (b) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93.
15. (c) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandan, A. J. Am. Chem. Soc. 1995, 117, 7544.
16. (d) Feldman, K S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722 and references cited therein.
17. (a) Zhdankin, V. V.; Crittell, C. M.; Stang, P. J.; Zefirov, N. S. Tetrahedron Lett. 1990, 31, 4821.
18. (b) Bachi, M. D.; Bar-Ner, N.; Crittell, C. M.; Stang, P. J.; Williamson, B. L. J. Org. Chem. 1991, 56, 3912.
19. Davidson, B. S. Chem. Rev. 1993, 93, 1771.
20. For an example of the direct alkylation of alkynyl(aryl)iodonium salts on iodine by organolithium reagents, see: Margida, A. J.; Koser, G. F. J. Org. Chem. 1984, 49, 4703.
21. The assigned regiochemistry of the thiazoles was confirmed by comparison with commercially available 6b and independently prepared 6a. An alternative, third mechanism involving the direct Michael addition of the thioamide nitrogen on the alkynyl(ary)iodonium species, is unlikely since the thioamide sulfur atom is far more nucleophilic: Walter, W.; Voss, J. In The Chemistry of Amides; Zabicky, J., Ed.; Wiley: New York, 1970; Part 1, pp 383-475.
22. Blechert, S. Synthesis 1989, 71.
23. (a) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 1319.
24. (b) Gately, D. A.; Luther, T. A.; Norton, J. R.; Miller, M. M.; Anderson, O. P J. Org. Chem. 1992, 57, 6496.
25. (c) Ochiai, M.; Ito, T. J. Org. Chem. 1995, 60, 2274.
26. 2 Since we also use a thioamide as starting material, our method can be considered, in a distant sense, as a variation of the Hantzsch synthesis.