Skraup喹啉合成

苯胺,甘油,硫酸和氧化剂 (如PhNO2)反应制备喹啉的反应。

反应机理

甘油在酸性条件下先生成丙烯醛,苯胺对其进行共轭加成β-苯胺基丙醛,关环脱水得到二氢喹啉,氧化得到产物。

反应实例

参考文献

1. (a) Skraup, Z. H. Monatsh. Chem. 1880, 1, 316. Zdenko Hans Skraup (1850􀀐-1910) was born in Prague, Czechoslovakia. He apprenticed under Lieben at the University of Vienna. (b) Skraup, Z. H. Ber. 1880, 13, 2086.【Zdenko Hans Skraup (1850􀀐-1910)生于捷克斯洛伐克的布拉格。在维亚纳大学师从Lieben。】

2. Manske, R. H. F.; Kulka, M. Org. React. 1953, 7, 80-􀀐99. (Review).

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8. Panda, K.; Siddiqui, I.; Mahata, P. K.; Ila, H.; Junjappa, H. Synlett 2004, 449-􀀐452.

9. Moore, A. Skraup Doebner–von Miller Reaction. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 488􀀐-494. (Review).

10. Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006, 71, 1668􀀐1676. Mechanistic study using 13C-labelled α,β-unsaturated ketones.

11. Vora, J. J.; Vasava, S. B.; Patel, Asha D.; Parmar, K. C.; Chauhan, S. K.; Sharma, S. S. E. J. Chem. 2009, 6, 201􀀐-206.

12. Fotie, J.; Kemami Wangun, H. V.; Fronczek, F. R.; Massawe, N.; Bhattarai, B. T. Rhodus, J. L.; Singleton, T. A.; Bohle, D. S. J. Org. Chem. 2012, 77, 2784-􀀐2790.

编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Skraup quinoline synthesis,page 562-563.

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