Synthesis of 4-Ynamides and Cyclization by the Vilsmeier Reagent to Dihydrofuran-2(3H)-ones

被引：44

作者：

Zhang, Zhaocheng ^{[2
]}

Kumar, Rapolu Kiran ^{[1
]}

Li, Guangzhi ^{[2
]}

Wu, Dongmei ^{[2
]}

Bi, Xihe ^{[1
,2
,3
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

[2] Jiamusi Univ, Coll Pharm, Jiamusi 154007, Peoples R China

[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

关键词：

PROPARGYLIC ALCOHOLS; DIVERGENT SYNTHESIS; AMIDE SYNTHESIS; VINYL AZIDES; CYCLOISOMERIZATION; EFFICIENT; ACIDS; HYDROAZIDATION; CYCLOADDITION; ALKYNYLATION;

D O I：

10.1021/acs.orglett.5b03189

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The room-temperature nucleophilic addition of vinyl azides to propargylic alcohols under BF3 center dot Et2O catalysis provides an efficient synthesis of 4-ynamides. The procedure is operationally convenient, shows broad substrate scope, and is viable for the synthesis of multifunctional 4-ynamides. Further, a Vilsmeier intramolecular cyclization of 4-ynamides into dihydrofuran-2(3H)-ones has also been discovered, which represents the first report of alkynes being used as the nucleophiles in Vilsmeier-type reactions.

引用

页码：6190 / 6193

页数：4

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