Reissert反应

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喹啉或异喹啉在酰卤和氰基源存在下进行三组分缩合得到Reissert化合物,而后水解得到醛,喹啉羧酸和氨气的反应

该反应中使改用N-氧化物的变体形式被称为Reissert-Henze反应。



反应机理



反应实例




不对称有机催化剂催化下Reissert化合物进行烯丙位烷基化反应。


参考文献

1. (a) Reissert, A. Ber. 1905, 38, 1603–1614. (b) Reissert, A. Ber. 1905, 38, 3415–3435. Carl Arnold Reissert was born in 1860 in Powayen, Germany. He received his Ph.D.In 1884 at Berlin, where he became an assistant professor. He collaborated with Tiemann. Reissert later joined the faculty at Marburg in 1902.

2. Popp, F. D. Adv. Heterocycl. Chem. 1979, 24, 187–214. (Review).

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7. Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989–1999.

8. Sieck, O.; Schaller, S.; Grimme, S.; Liebscher, J. Synlett 2003, 337–340.

9. Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491–1508. (Review).

10. Gibson, H. W.; Berg, M. A. G.; Clifton Dickson, J.; Lecavalier, P. R.; Wang, H.;Merola, J. S. J. Org. Chem. 2007, 72, 5759–5770.

11. Fuchs, C.; Bender, C.; Ziemer, B.; Liebscher, J. J. Heterocycl. Chem. 2008, 45, 1651–1658.

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编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Reissert reaction,page 510-511.

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