Niementowski喹唑啉合成反应

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    邻氨基苯甲酸和酰胺加热缩合得到喹唑啉酮的反应。另外此反应也可以靛红酸酐为底物和酰胺缩合得到喹唑啉产物,邻酰胺基苯甲酸和氨缩合也可以得到产物。


反应机理


反应实例

2-Acetoxymethyl-5,7-dimethyl-3-(2-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl ester (9). To acetylanthranilic acid 7 (6 mmol) in MeCN was added aniline 8 (8 mmol) in MeCN (10 mL) at r.t. PCl3 (12 mmol) was added via syringe to the white suspension and the mixture was heated for 2 h to 50 ℃ with stirring. After cooling to r.t., the mixture was diluted with EA and quenched with 1N aq HCl. The organic layer was washed (10% aq KHCO3) and evaporated in vacuo. The oil crystallized on standing. Recrystallization from ethanol:water (1:1) gave 9 (92%),

mp 124–127 ℃.

【McKenna J,  J Org Chem., 2004, 69, 6474】


相关文献

1 Meyer VE, Bellmann Th J Prakt Chem 1886 33 18

2 Niementowski VS J Prakt Chem 1895 51 564

3 Endicot MM J Am Chem Soc 1946 68 1299

4 Pater R J Heterocycl Chem 1970 7 1113

5 Pater R J Heterocycl Chem 1971 8 699

6R Hisano T Org Prep Proced Int 1973 5 145

7 Cuny E Tet Lett 1980 21 3029

8 McKenna J J Org Chem 2004 69 6474

9 Lamberth C Tet Lett 2010 51 2652


编译自:Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 345.




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