K2CO3-catalyzed synthesis of chromones and 4-quinolones through the cleavage of aromatic C-O bonds

Organic Letters
Jie ZhaoHua Fu

Abstract

Phenol-derived electrophiles are favorable substrates because phenols are naturally abundant or can be readily prepared from other aromatic compounds. However, the cleavage of aromatic C-O bonds is a great challenge because of their high energy. K(2)CO(3)-catalyzed intramolecular cyclization of 1-(2-alkoxyphenyl)-3-akylpropane-1,3-dione and 3-(alkylimino)-1-(2-methoxyphenyl)-2-methylpropan-1-one derivatives via the selective cleavage of aromatic C-O bonds is reported. The corresponding chromone and 4-quinolone derivatives were obtained in reasonable yields.

References

Apr 2, 1996·Proceedings of the National Academy of Sciences of the United States of America·W F De AzevedoS H Kim
Mar 20, 2001·Current Pharmaceutical Design·V E Anderson, N Osheroff
May 9, 2002·Chemical Reviews·Jwanro HassanMarc Lemaire
Nov 28, 2002·Pharmacology & Therapeutics·Bent H Havsteen
Mar 13, 2003·Chemical Reviews·Douglas A HortonMark L Smythe
Apr 16, 2003·Accounts of Chemical Research·Stephen J Blanksby, G Barney Ellison
Jun 6, 2003·Journal of the American Chemical Society·Simon B Blakey, David W C MacMillan
Sep 25, 2003·Journal of the American Chemical Society·Hanh Nho NguyenStephen L Buchwald
Mar 5, 2004·Journal of the American Chemical Society·Fumitoshi KakiuchiShinji Murai
Nov 5, 2005·The Journal of Organic Chemistry·Michael E LimmertJohn F Hartwig
Nov 10, 2006·Chemical Reviews·Anna RoglansMarcial Moreno-Mañas
May 23, 2008·Angewandte Chemie·Mamoru TobisuNaoto Chatani
Oct 9, 2008·Journal of the American Chemical Society·Kyle W QuasdorfNeil K Garg
Oct 14, 2008·Journal of the American Chemical Society·Bing-Tao GuanZhang-Jie Shi
Nov 26, 2009·Journal of the American Chemical Society·Aurora Antoft-FinchVictor Snieckus
Nov 26, 2009·Journal of the American Chemical Society·Kyle W QuasdorfNeil K Garg
Sep 21, 2010·Accounts of Chemical Research·Da-Gang YuZhang-Jie Shi
Dec 8, 2010·Chemical Reviews·Brad M RosenVirgil Percec
Apr 23, 2011·Science·Alexey G Sergeev, John F Hartwig

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Citations

Jun 26, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana PintoArtur M S Silva
Jan 14, 2016·Chemical Reviews·Lin ZhangQun Liu
Oct 20, 2015·Chemical Communications : Chem Comm·Jianming LiuAiwen Lei
Jan 19, 2016·Chemical Communications : Chem Comm·Jinhai ShenXiuling Cui
Jul 31, 2019·Organic & Biomolecular Chemistry·Jing-Wen ZhangDan-Yun Chen
Nov 28, 2013·Chemical Communications : Chem Comm·Xuesong WangXiuling Cui
Oct 25, 2017·Beilstein Journal of Organic Chemistry·Yanhui GuoJie-Ping Wan
May 15, 2020·The Journal of Organic Chemistry·Narva Deshwar KushwahaSuraj Raosaheb Shinde
Aug 30, 2017·The Journal of Organic Chemistry·Qiujie TangAihua Zhou
Feb 3, 2018·The Journal of Organic Chemistry·Meng-Yang ChangHeui-Sin Wang

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