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

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• 作者：Zhaocheng Zhang ; Rapolu Kiran Kumar ; Guangzhi Li ; Dongmei Wu ; Xihe Bi
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：December 18, 2015
• 年：2015
• 卷：17
• 期：24
• 页码：6190-6193
• 全文大小：357K
• ISSN：1523-7052

文摘

The room-temperature nucleophilic addition of vinyl azides to propargylic alcohols under BF₃路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.