Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication

被引：32
|
作者：
Shen, Xianyan [1 ,2 ]
Zhou, Qiang [1 ]
Xiong, Wei [1 ,2 ]
Pu, Wenchen [1 ]
Zhang, Wei [3 ]
Zhang, Guolin [1 ]
Wang, Chun [1 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Chongqing Inst Green & Intelligent Technol, Chongqing 400714, Peoples R China
来源：
TETRAHEDRON | 2017年 / 73卷 / 32期
基金：
中国国家自然科学基金;
关键词：
Flavonol; Synthesis; AFO; Mechanism; DERIVATIVES; CYCLIZATION; KINETICS;
D O I：
10.1016/j.tet.2017.06.064
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5 substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ H-1 NMR analysis indicated that the epoxide was involved in the transformation from chalcone to flavonol and/or aurone under alkaline base/peroxide conditions. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4822 / 4829
页数：8
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