Paal–Knorr呋喃合成

酸催化下1,4-二酮环化得到呋喃的反应。

反应机理

反应实例

呋喃生成的同时溴被脱去。

参考文献

1. (a) Paal, C. Ber. 1884, 17, 2756􀀐-2767. (b) Knorr, L. Ber. 1885, 17, 2863-􀀐2870. (c) Paal, C. Ber. 1885, 18, 367-􀀐371.

2. Friedrichsen, W. Furans and Their Benzo Derivatives: Synthesis. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 2, 351􀀐393. (Review).

3. de Laszlo, S. E.; Visco, D.; Agarwal, L.; et al. Bioorg. Med. Chem. Lett. 1998, 8, 2689-􀀐2694.

4. Gupta, R. R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry, Springer: New York,1999; Vol. 2, 83-􀀐84. (Review).

5. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell Science: Cambridge, 2000; 308􀀐-309. (Review).

6. Mortensen, D. S.; Rodriguez, A. L.; Carlson, K. E.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2001, 44, 3838-􀀐3848.

7. König, B. Product Class 9: Furans. In Science of Synthesis: Houben􀀐Weyl Methods of Molecular Transformations; Maas, G., Ed.; Georg Thieme Verlag: New York, 2001; Cat. 2, Vol. 9, 183-􀀐278. (Review).

8. Shea, K. M. Paal–Knorr Furan Synthesis. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 168-􀀐181. (Review).

9. Kaniskan, N.; Elmali, D.; Civcir, P. U. ARKIVOC 2008, 17-􀀐29.

10. Yin, G.; Wang, Z.; Chen, A.; Gao, M.; Wu, A.; Pan, Y. J. Org. Chem. 2008, 73,

3377-􀀐3383.

11. Wang, G.; Guan, Z.; Tang, R.; He, Y. Synth. Commun. 2010, 40, 370–377.

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li,  Paal–Knorr furan synthesis，page 452-453.