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

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

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 24; pp. 6190 - 6193
Main Authors Zhang, Zhaocheng, Kumar, Rapolu Kiran, Li, Guangzhi, Wu, Dongmei, Bi, Xihe
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.12.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
AMIDE SYNTHESIS
VINYL AZIDES
ACIDS
PROPARGYLIC ALCOHOLS
DIVERGENT SYNTHESIS
CYCLOISOMERIZATION
EFFICIENT
ALKYNYLATION
HYDROAZIDATION
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Summary:The room-temperature nucleophilic addition of vinyl azides to propargylic alcohols under BF3·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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03189