
β-酮基酯和羟胺环化得到3-羟基-异恶唑(3-异恶唑酚)的反应,称为Claisen异恶唑合成。

由于β-酮基酯有酯基和酮两个反应位点,此反应有个副反应得到5-异恶唑酮:
反应实例

【J. Org. Chem. 2000, 65, 1003-1007】

【J. Med. Chem. 2001, 44, 1051-1059】
相关文献
1. (a) Claisen, L; Lowman, O. E. Ber. 1888, 21, 784. (b) Claisen, L.; Zedel, W. Ber.1891, 24, 140. (c) Hantzsch, A. Ber. 1891, 24, 495-506.
2. Barnes, R. A. In Heterocyclic Compounds; Elderfield, R. C., Ed.; Wiley: New York, 1957; Vol. 5, p 474ff. (Review).
3. Loudon, J. D. In Chemistry of Carbon Compounds; Rodd, E. H., Ed.; Elsevier: Amsterdam,1957; Vol. 4a, p. 345ff. (Review).
4. McNab, H. Chem. Soc. Rev. 1978, 7, 345-358. (Review).
5. Chen, B.-C. Heterocycles 1991, 32, 529-597. (Review).
6. Fr?lund, B.; Kristiansen, U.; Brehm, L.; Hansen, A. B.; Krogsgaard-Larsen, K.; Falch, E. J. Med. Chem. 1995, 38, 3287-3296.
7. Sorensen, U. S.; Falch, E.; Krogsgaard-Larsen, K. J. Org. Chem. 2000, 65,1003-1007.
8. Madsen, U.; Br?uner-Osborne, H.; Frydenvang, K.; Hvene, L.; Johansen, T.N.; Nielsen, B.; Sánchez, C.; Stensb?l, T.B.; Bischoff, F.; Krogsgaard-Larsen, K. J. Med. Chem. 2001, 44, 1051-1059.
9. Brooks, D. A. Claisen Isoxazole Synthesis. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 220-224. (Review).
10. El Shehry, M. F.; Swellem, R. H.; Abu-Bakr, Sh. M.; El-Telbani, E. M. Eur. J. Med. Chem. 2010, 45, 4783-4787.
编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Claisen isoxazole synthesis, page 138-139.
2022-8-22 摘自 有机合成公众号