Facile construction of 4H-chromenes via Michael addition of phenols to benzylidene oxobutanoates and their successful conversion into pyranocoumarins

被引：7
|
作者：
Priyanka [1 ]
Sharma, Rajesh K. [1 ]
Butcher, Ray J. [2 ]
Katiyar, Diksha [1 ]
机构：
[1] Banaras Hindu Univ, MMV, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[2] Howard Univ, Dept Chem, 525 Coll St NW, Washington, DC 20059 USA
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 24期
关键词：
4H-Chromenes; Michael addition; Benzylidene oxobutanoates; Linear pyranocoumarins; Angular pyranocoumarins; ONE-POT SYNTHESIS; FUNCTIONALIZED; 4H-CHROMENES; TANDEM REACTION; 3-COMPONENT REACTION; SELECTIVE SYNTHESIS; DERIVATIVES; COUMARINS; BENZYLATION; EFFICIENT; ADDITION/ANNULATION;
D O I：
10.1016/j.tetlet.2018.05.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and simple approach for the synthesis of functionalized 4H-chromenes has been developed via acid catalyzed Michael addition of phenols to benzylidene oxobutanoates. Preliminary mechanistic studies were conducted, suggesting that intermediate chroman derivative is initially formed which on dehydration produces final 4H-chromene. The conversion of 4H-chromenes into linear and angular pyranocoumarins is also described. The structural arrangements between the pyran and coumarin rings have been established by X-ray crystallographic analysis and 2D NMR spectroscopy. (C)2018 Elsevier Ltd. All rights reserved.
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收藏
页码：2347 / 2351
页数：5
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