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Erlenmeyer-Plöchl azlactone synthesis2019-04-04

在乙酸酐存在下酰基甘氨酸发生分子内缩合得到5-恶唑酮(吖内酯)。

反应机理:


反应实例:


参考文献:

1. Plöchl, J. Ber. Dtsch. Chem. Ges. 1884, 17, 1616.

2. Erlenmeyer, E., Jr. Ann. 1893, 275, 1. Emil Erlenmeyer, Jr. (18641921) was born in

Heidelberg, Germany to Emil Erlenmeyer (18251909), a famous chemistry professor

at the University of Heidelberg. He investigated the ErlenmeyerPlöchl azlactone

synthesis while he was a Professor of Chemistry at Strasburg.

3. Carter, H. E. Org. React. 1946, 3, 198239. (Review).

4. Baltazzi, E. Quart. Rev. Chem. Soc. 1955, 9, 150. (Review).

5. Filler, R.; Rao, Y. S. New Development in the Chemistry of Oxazolines, In Adv. Heterocyclic

Chem; Katritzky, A. R. and Boulton, A. J., Eds; Academic Press, Inc: New

York, 1977, Vol. 21, pp. 175206. (Review).

6. Kumar, P.; Mishra, H. D.; Mukerjee, A. K. Synthesis 1980, 10, 836.

7. Mukerjee, A. K.; Kumar, P. Heterocycles 1981, 16, 1995. (Review).

8. Mukerjee, A. K. Heterocycles 1987, 26, 1077. (Review).

9. Cornforth, J.; Ming-hui, D. J. Chem. Soc. Perkin Trans. I 1991, 2183.

10. Ivanova, G. G. Tetrahedron 1992, 48, 177.

11. Combs, A. P.; Armstrong, R. W. Tetrahedron Lett. 1992, 33, 6419.

12. Monk, K. A.; Sarapa, D.; Mohan, R. S. Synth. Commun. 2000, 30, 3167.

13. Konkel, J. T.; Fan, J.; Jayachandran, B.; Kirk, K. L. J. Fluorine Chem. 2002, 115, 27.

14. Buck, J. S.; Ide, W.S. Org. Synth. Coll. 1943, 2, 55.

15. Brooks, D. A. ErlenmeyerPlöchl Azlactone Synthesis in Name Reactions in Heterocyclic

Chemistry, Li, J. J.; Corey, E. J., Eds.; Wiley & Sons: Hoboken, NJ, 2005,

229233. (Review).

编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Erlenmeyer-Plöchl azlactone synthesis, page 212-213.

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