NaH Promoted One-Pot Tandem Reactions of 3-(1-Alkynyl) Chromones to Form 2-Nitrogen-Substituted Xanthones

被引：4

作者：

Duan, Wen-Di ^{[1
,2
]}

Zhang, Yu-Fang ^{[1
,2
]}

Hu, Youhong ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ACS OMEGA | 2020年 / 5卷 / 22期

关键词：

INSERTION;

D O I：

10.1021/acsomega.0c01930

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A silver-catalyzed dimerization of ethyl isocyanoacetates could trigger the tandem reaction of 3-(1-alkynyl) chromones under the basic condition in a one-pot reaction to afford xanthone skeletons with 2-imidazolyl substitution in an efficient manner. With the control experiment in hand, a mechanism including dimerization of isocyanoacetate/deprotonation/Michael addition/ring-opening/ cyclization 1,2-elimination was deduced. Further investigation for the base was carried out, resulting in NaH as an optimal base to avoid the dimerization of 3-(1-alkynyl) chromones. The scope of this methodology was extended on the different substituents of 3-(1-alkynyl)-chromones and the potential of other N-heterocycle glycine ester anions to give the novel functional 2-nitrogen-derived xanthones.

引用

页码：13454 / 13461

页数：8

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