硫代二甘酸二乙酯和α-二酮在碱性条件下缩合得到3,4-二取代噻吩-2,5-二甲酸酯,然后水解生成相应的酸的反应。
反应机理
反应实例
参考文献
1. Hinsberg, O. Ber. 1910, 43, 901-906.
2. Miyahara, Y.; Inazu, T.; Yoshino, T. Bull. Chem. Soc. Jpn. 1980, 53, 1187-1188.
3. Gronowitz, S. In Thiophene and Its Derivatives, Part 1, Gronowitz, S., ed.; Wiley-Interscience: New York, 1985, pp 34-41. (Review).
4. Miyahara, Y.; Inazu, T.; Yoshino, T. J. Org. Chem. 1984, 49, 1177-1182.
5. Christl, M.; Krimm, S.; Kraft, A. Angew. Chem. Int. Ed. 1990, 29, 675-677.
6. Beye, N.; Cava, M. P. J. Org. Chem. 1994, 59, 2223-2226.
7. Vogel, E.; Pohl, M.; Herrmann, A.; Wiss, T.; König, C.; Lex, J.; Gross, M.;
Gisselbrecht, J. P. Angew. Chem. Int. Ed. 1996, 35, 1520-1525.
8. Mullins, R. J.; Williams, D. R. Hinsberg Synthesis of Thiophene Derivatives. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp
199-206. (Review).
9. Traversone, A.; Brill, W. K.-D. Tetrahedron Lett. 2007, 48, 3535-3538.
10. Jimenez, R. P.; Parvez, M.; Sutherland, T. C.; Viccars, J. Eur. J. Org. Chem. 2009,5635-5646.
编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Hinsberg synthesis of thiophenes,page 314-315.