Bischler–Napieralski反应

β-苯乙胺在三氯氧磷中回流得到二氢喹啉的反应。

反应机理

反应实例

非常规的Bischler–Napieralski反应

参考文献

1. Bischler, A.; Napieralski, B. Ber. 1893, 26, 1903–1908. Augustus Bischler discovered the Bischler–Napieralski reaction while studying alkaloids at Basel Chemical Works, Switzerland with his coworker, B. Napieralski. Bernard Napieralski was affiliated with the University of Zurich. （Augustus Bischler 和其合作者B. Napieralsk在瑞士巴塞尔化工厂研究生物碱的时候发现了Bischler–Napieralski 反应。Bernard Napieralski就职于苏黎世大学。）

2. Mechanistic studies: (a) Fodor, G.; Gal, J.; Phillips, B. A. Angew. Chem. Int. Ed. Engl.1972, 11, 919–920. (b) Nagubandi, S.; Fodor, G. J. Heterocycl. Chem. 1980, 17,1457–1463. (c) Fodor, G.; Nagubandi, S. Tetrahedron 1980, 36, 1279–1300.

3. Aubé, J.; Ghosh, S.; Tanol, M. J. Am. Chem. Soc. 1994, 116, 9009–9018.

4. Sotomayor, N.; Domínguez, E.; Lete, E. J. Org. Chem. 1996, 61, 4062–4072.

5. Wang, X.-j.; Tan, J.; Grozinger, K. Tetrahedron Lett. 1998, 39, 6609–6612.

6. Ishikawa, T.; Shimooka, K.; Narioka, T.; Noguchi, S.; Saito, T.; Ishikawa, A.; Yamazaki, E.; Harayama, T.; Seki, H.; Yamaguchi, K. J. Org. Chem. 2000, 65, 9143–9151.

7. Banwell, M. G.; Harvey, J. E.; Hockless, D. C. R., Wu, A. W. J. Org. Chem. 2000, 65, 4241–4250.

8. Capilla, A. S.; Romero, M.; Pujol, M. D.; Caignard, D. H.; Renard, P. Tetrahedron 2001, 57, 8297–8303.

9. Wolfe, J. P. Bischler–Napieralski Reaction. In Name Reactions in Heterocyclic Chemistry;Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 376􀀐385. (Review).

10. Ho, T.-L.; Lin, Q.-x. Tetrahedron 2008, 64, 10401–10405.

11. Csomós, P.; Fodor, L.; Bernáth, G.; Csámpai, A.; Sohár, P. Tetrahedron 2009, 65,1475–1480.

12. Buyck, T.; Wang, Q.; Zhu, J. Org. Lett. 2012, 14, 1338–1341.

编译自：J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Bischler–Napieralski reaction，page 56-57.