Robinson–Gabriel反应

2-酰基胺基酮环化脱水得到2,5-二或2,4,5-三烷基，芳基或杂芳基恶唑的反应。

反应机理

反应实例

【J. Org. Chem. 1993, 58, 3604-3606】

【J. Am. Chem. Soc. 1995, 117, 558-559】

【Tetrahedron Lett. 2005, 46, 6285–6288】

【Angew. Chem. Int. Ed. 2006, 45, 6714-6718】

3-(2-Ethyloxazol-5-yl)-1H-indole (4). 3 (0.1 g, 0.43 mmol) in 5 mL POCl3 was stirred 18 h (r.t.),evaporated, and the residue in 50 mL EA washed (NaHCO3). Workup afforded, 82 mg, 90% of 4,mp 161–163 ℃.

【Tetrahedron, 2010, 66, 4888】

【Tetrahedron Lett. 2012, 53, 1998–2000】

参考文献

1. (a) Robinson, R. J. Chem. Soc. 1909, 95, 2167-2174. (b) Gabriel, S. Ber. 1910, 43, 134-138. (c) Gabriel, S. Ber. 1910, 43, 1283-1287.

2. Turchi, I. J. In The Chemistry of Heterocyclic Compounds, 45; Wiley: New York,1986; pp 1-342. (Review).

3. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604-3606.

4. Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558-559.

5. Morwick, T.; Hrapchak, M.; DeTuri, M.; Campbell, S. Org. Lett. 2002, 4, 2665-2668.

6. Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; Huang, X.; Chen, D.Y.-K.; Snyder, S. A. Angew. Chem. Int. Ed. 2003, 42, 1753-1758.

7. Godfrey, A. G.; Brooks, D. A.; Hay, L. A.; Peters, M.; McCarthy, J. R.; Mitchell, D. J.Org. Chem. 2003, 68, 2623-2632.

8. Brooks, D. A. Robinson–Gabriel Synthesis. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, 249-253. (Review).

9. Yang, Y.-H.; Shi, M. Tetrahedron Lett. 2005, 46, 6285–6288.

10. Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Angew. Chem. Int. Ed. 2006, 45, 6714-6718.

11. Shaw, A. Y.; Xu, Z.; Hulme, C. Tetrahedron Lett. 2012, 53, 1998–2000.

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Robinson–Gabriel synthesis，page 521-522.