A General and Efficient Synthesis of 2-Pyridones, 2-Quinolinones, and 1-Isoquinolinones from Azine N-Oxides

作者:Wang, Dong*; Zhao, Junjie; Wang, Yuxi; Hu, Jianyong; Li, Linna; Miao, Longfei; Feng, Hairong; Desaubry, Laurent; Yu, Peng*
来源:Asian Journal of Organic Chemistry, 2016, 5(12): 1442-1446.
DOI:10.1002/ajoc.201600430

摘要

2-Pyridones, 2-quinolinones, and 1-isoquinolinones are critical building blocks in medicinal chemistry. These N-heterocycles, however, remain a challenge to synthesize by current methods. A mild, general, and efficient approach for the synthesis of these hydroxyl N-heteroarenes was developed by employing bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP) as an activating agent and sodium acetate/water as the base/nucleophile combination. The reaction mechanism, especially the dual function of sodium acetate as the base and nucleophile, has been proposed on the basis of results from isotopic labeling experiments.