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

Boris A. Trofimov*, Olesya A. Shemyakina, Anastasiya G. Mal’kina, Igor’ A. Ushakov, Olga N. Kazheva, Grigorii G. Alexandrov and Oleg A. Dyachenko

*A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Email: boris_trofimovirioch.irk.ru

B. A. Trofimov, O. A. Shemyakina, A. G. Mal'kina, I. A. Ushakov, O. N. Kazheva, G. G. Alexandrov, O. A. Dyachenko, Org. Lett., 2010, 12, 3200-3203.

DOI: 10.1021/ol1011532 (free Supporting Information)


Abstract

An unexpected facile domino reaction of α,β-acetylenic γ-hydroxy nitriles with arenecarboxylic acids affords 4-cyano-3(2H)-furanones in good yield. The reaction is triggered by the addition of an arenecarboxylic acid to a triple bond, followed by intramolecular transesterification-enol formation and Claisen condensation of the ketoacetonitrile tautomer with ester functional group.

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Key Words

3(2H)-furanones


ID: J54-Y2010-1940