Ritter反應(yīng)

未來awtahy2g4v 2020-06-07

展開全文

在強酸環(huán)境下醇和腈反應(yīng)制備酰胺的反應(yīng)。叔碳或芐位的碳正離子比較穩(wěn)定，如果體系中有合適的親核試劑，碳正離子可以與這些親核試劑反應(yīng)。利用這一點，如果在體系中加入腈，酰胺，疊氮等親核試劑做胺源，可以制備各種胺或胺的衍生物。

含有氰基的底物在進行脫Boc時，脫掉的叔丁基正離子會和氰基進行Ritter反應(yīng)得到N-叔丁基酰胺副產(chǎn)物。

反應(yīng)機理

反應(yīng)實例

【J. Org. Chem. 1981, 46, 78-82】

【J. Org. Chem. 1989, 54, 2242-2244】

【Synthesis, 1997,9, 1034-1040】

A solution of 1-adamantanol (0.304 g, 2 mmol)and urea (0.24 g, 4 mmol) in TFA (1.54 mL, 20 mmol) was heated at 115-120^oCfor 7 hr. After the reaction was complete, the mixture was kept at r.t.overnight. Then acetone (2 mL) was added to and precipitate was formed. Thecrude product was filtratrated after cooling, washed with pentane and dried togive 0.43 g target compound (83%).

【Tetrahedron Lett. 2001, 42, 5175-5176】

【J. Org. Chem. 2004, 69, 5906-5925】

【Org. Lett. 2013, 15, 546-549】

Prins/Ritter串聯(lián)反應(yīng)

相關(guān)文獻

1. (a) Ritter, J. J.; Minieri, P. P. J. Am. Chem. Soc. 1948, 70, 4045-4048. (b) Ritter, J. J.; Kalish, J. J. Am. Chem. Soc. 1948, 70, 4048-4050.

2. Krimen, L. I.; Cota, D. J. Org. React. 1969, 17, 213–329. (Review).

3. Top, S.; Jaouen, G. J. Org. Chem. 1981, 46, 78-82.

4. Schumacher, D. P.; Murphy, B. L.; Clark, J. E.; Tahbaz, P.; Mann, T. A. J. Org. Chem.1989, 54, 2242-2244.

5. Le Goanvic, D; Lallemond, M.-C.; Tillequin, F.; Martens, T. Tetrahedron Lett. 2001,42, 5175-5176.

6. Tanaka, K.; Kobayashi, T.; Mori, H.; Katsumura, S. J. Org. Chem. 2004, 69,5906-5925.

7. Nair, V.; Rajan, R.; Rath, N. P. Org. Lett. 2002, 4, 1575-1577.

8. Concellón, J. M.; Riego, E.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Org. Lett. 2004, 6, 4499-4501.

9. Brewer, A. R. E. Ritter reaction. In Name Reactions for Functional Group Transformations; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2007, pp 471-476. (Review).

10. Baum, J. C.; Milne, J. E.; Murry, J. A.; Thiel, O. R. J. Org. Chem. 2009, 74,2207-2209.

11. Yadav, J. S.; Reddy, Y. J.; Reddy, P. A. N.; Reddy, B. V. S. Org. Lett. 2013, 15, 546-549.

編譯自：J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Ritter reaction，page 517-518.