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A General and Efficient Synthesis of 2‐Pyridones, 2‐Quinolinones, and 1‐Isoquinolinones from Azine N ‐Oxides
Author(s) -
Wang Dong,
Zhao Junjie,
Wang Yuxi,
Hu Jianyong,
Li Linna,
Miao Longfei,
Feng Hairong,
Désaubry Laurent,
Yu Peng
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600430
Subject(s) - chemistry , nucleophile , azine , combinatorial chemistry , hexafluorophosphate , sodium acetate , base (topology) , organic chemistry , catalysis , ionic liquid , mathematical analysis , mathematics
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.