Paal–Knorr吡咯合成

1,4-二酮和伯胺（或氨）反应制备吡咯的反应。此反应是Knorr吡唑合成的变体。

反应机理

反应实例

参考文献

1. (a) Paal, C. Ber. 1885, 18, 367􀀐371. (b) Paal, C. Ber. 1885, 18, 2251􀀐2254. (c) Knorr, L. Ber. 1885, 18, 299-􀀐311.

2. Corwin, A. H. Heterocyclic Compounds Vol. 1, Wiley, NY, 1950; Chapter 6. (Review).

3. Jones, R. A.; Bean, G. P. The Chemistry of Pyrroles, Academic Press, London, 1977, pp 51􀀐57, 74􀀐-79. (Review).

4. (a) Brower, P. L.; Butler, D. E.; Deering, C. F.; Le, T. V.; Millar, A.; Nanninga, T. N.; Roth, B. D. Tetrahedron Lett. 1992, 33, 2279-2282. (b) Baumann, K. L.; Butler, D. E.; Deering, C. F.; Mennen, K. E.; Millar, A.; Nanninga, T. N.; Palmer, C. W.; Roth, B.D. Tetrahedron Lett. 1992, 33, 2279, 2283-􀀐2284.

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

6. Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-􀀐3300.

7. Quiclet-Sire, B.; Quintero, L.; Sanchez-Jimenez, G.; Zard, Z. Synlett 2003, 75􀀐-78.

8. Gribble, G. W. Knorr and Paal􀀐Knorr Pyrrole Syntheses. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Corey, E. J., Eds, Wiley: Hoboken, NJ, 2005, 77-􀀐88.(Review).

9. Salamone, S. G.; Dudley, G. B. Org. Lett. 2005, 7, 4443-4445.

10. Fu, L.; Gribble, G. W. Tetrahedron Lett. 2008, 49, 7352-􀀐7354.

11. Trushkov, I. V.; Nevolina, T. A.; Shcherbinin, V. A.; Sorotskaya, L. N.; Butin, A. V. Tetrahedron Lett. 2013, 54, 3974􀀐-3976.

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li,  Paal–Knorr pyrrole synthesis，page 454-455.

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类似反应

Knorr吡唑合成

2015-11-24 有机合成

肼或取代肼和1,3-二羰基化合物反应得到吡唑或吡唑酮的反应。此反应与 Paal–Knorr 吡咯合成法类似。

反应机理

此反应的机理有两种可能：

肼的两个氮原子同时进攻两个羰基。

肼的一个氮原子先进攻其中一个亲电性较强的羰基。

反应实例

参考文献

1 Knorr, L. Ber Dtsch. Chem. Ges. 1883, 16, 2597. Ludwig Knorr (1859􀀐1921) was

born near Munich, Germany. After studying under Volhard, Emil Fischer, and Bunsen,

he was appointed professor of chemistry at Jena. Knorr made tremendous contributions

in the synthesis of heterocycles in addition to discovering the important pyrazolone

drug, pyrine.

2 Knorr, L. Ber Dtsch. Chem. Ges. 1884, 17, 546, 2032.

3 Knorr, L. Ber Dtsch. Chem. Ges. 1885, 18, 311.

4 Knorr, L., Justus Liebigs Ann. Chem. 1887, 238, 137.

5 Burness, D. M. J. Org. Chem. 1956, 21, 97.

6 Jacobs, T. L., in Heterocyclic Compounds, Elderfield, R. C., Ed.; Wiley: New York,

1957, 5, 45. (Review).

7 Houben-Weyl, 1967, 10/2, 539, 587, 589, 590. (Review).

8 Marzinzik, A. L.; Felder, E. R. Tetrahedron Lett. 1996, 37, 1003.

9 Elguero, J., In Comprehensive Heterocyclic Chemistry II, Katrizky, A. R.; Rees, C.

W.: Scriven, E. F. V., Eds; Elsevier: Oxford, 1996, 3, 1. (Review).

10 Penning, T. D.; Talley, J. J.; et al. J. Med. Chem. 1997, 40, 1347.

11 Shen, D-M.; Shu, M.; Chapman, K. T. Org. Lett. 2000, 2, 2789.

12 Stanovnik, E.; Svete, J. in Science Of Synthesis, 2002, 12, 15; Ed. by Neier, R.;

Thieme. (Review).

13 Carpino, P. A.; Lefker, B. A.; Toler, S. M.; et al. Bioorg. Med. Chem. 2003,11, 581.

14 Sakya, S. M. Knorr Pyrazole Synthesis In Name Reactions in Heterocyclic Chemistry,

Eds, Li, J. J.; Corey, E. J. Wiley & Sons: Hoboken, NJ, 2005, 292􀀐300. (Review).

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Knorr pyrazole synthesis，page 331-332.