Pechmann香豆素合成
Brønstedt酸或 Lewis 酸催化下酚和β-酮酯缩合得到香豆素类似物的反应。此反应也被称为von Pechmann 环化反应。
反应机理
首先在酸催化下两个底物先生成酯,然后烯醇化进行迈克尔加成,重新芳香化,脱水得到产物。
反应实例
参考文献
1. von Pechmann, H.; Duisberg, C. Ber. 1883, 16, 2119. Hans von Pechmann
(1850-1902) was born in Nürnberg, Germany. After his doctorate, he worked with
Frankland and von Baeyer. Pechmann taught at Munich and Tübingen. He committed suicide at 52 by taking cyanide.【 Hans von Pechmann
(1850-1902)生于德国纽伦堡。博士毕业后与Frankland 和 von Baeyer一起工作。任教于慕尼黑大学和蒂宾根大学。于52岁时服氰化物自杀。】
2. Corrie, J. E. T. J. Chem. Soc., Perkin Trans. 1 1990, 2151–2997.
3. Hua, D. H.; Saha, S.; Roche, D.; Maeng, J. C.; Iguchi, S.; Baldwin, C. J. Org. Chem.1992, 57, 399–403.
4. Li, T.-S.; Zhang, Z.-H.; Yang, F.; Fu, C.-G. J. Chem. Res., (S) 1998, 38–39.
5. Potdar, M. K.; Mohile, S. S.; Salunkhe, M. M. Tetrahedron Lett. 2001, 42, 9285–9287.
6. Khandekar, A. C.; Khandilkar, B. M. Synlett. 2002, 152–154.
7. Smitha, G.; Sanjeeva Reddy, C. Synth. Commun. 2004, 34, 3997–4003.
8. De, S. K.; Gibbs, R. A. Synthesis 2005, 1231–1233.
9. Manhas, M. S.; Ganguly, S. N.; Mukherjee, S.; Jain, A. K.; Bose, A. K. Tetrahedron Lett. 2006, 47, 2423–2425.
10. Rodriguez-Dominguez, J. C.; Kirsch, G. Synthesis 2006, 1895–1897.
11. Ouellet, S. G.; Gauvreau, D.; Cameron, M.; Dolman, S.; Campeau, L.-C.; Hughes, G.; O’Shea, P. D.; Davies, I. W. Org. Process Res. Dev. 2012, 16, 214-219.
编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Pechmann coumarin synthesis,page 466-467.