Niementowski喹唑啉合成反应
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
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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
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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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