A Domino Reaction of α,β-Acetylenic γ-Hydroxy Nitriles with Arenecarboxylic Acids: An Unexpected Facile Shortcut to 4-Cyano-3(2H)-furanones

An unexpected facile domino reaction of α,β-acetylenic γ-hydroxy nitriles with arenecarboxylic acids (Et3N, MeCN, 20−25 °C, 48 h) affords 4-cyano-3(2H)-furanones in 67−86% yield. The reaction is triggered by the addition of an arenecarboxylic acid to a triple bond, followed by the domino reaction se...

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Bibliographic Details
Published in:Organic letters 2010-07, Vol.12 (14), p.3200-3203
Main Authors: Trofimov, Boris A, Shemyakina, Olesya A, Mal’kina, Anastasiya G, Ushakov, Igor’ A, Kazheva, Olga N, Alexandrov, Grigorii G, Dyachenko, Oleg A
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Carboxylic Acids - chemistry
Furans - chemistry
Nitriles - chemistry
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Summary:An unexpected facile domino reaction of α,β-acetylenic γ-hydroxy nitriles with arenecarboxylic acids (Et3N, MeCN, 20−25 °C, 48 h) affords 4-cyano-3(2H)-furanones in 67−86% yield. The reaction is triggered by the addition of an arenecarboxylic acid to a triple bond, followed by the domino reaction sequence: intramolecular transesterification−enol formation and Claisen condensation of the ketoacetonitrile tautomer with ester functional group.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1011532