A domino reaction of alpha,beta-acetylenic gamma-hydroxy nitriles with arenecarboxylic acids: an unexpected facile shortcut to 4-cyano-3(2H)-furanones.
An unexpected facile domino reaction of alpha,beta-acetylenic gamma-hydroxy nitriles with arenecarboxylic acids (Et(3)N, MeCN, 20-25 degrees 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.
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia. boris_trofimov@irioch.irk.ru
Boris A
BA
Trofimov
Olesya A
OA
Shemyakina
Anastasiya G
AG
Mal'kina
Igor' A
IA
Ushakov
Olga N
ON
Kazheva
Grigorii G
GG
Alexandrov
Oleg A
OA
Dyachenko
D000480:Alkynes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*
D000480:Alkynes; D002264:Carboxylic Acids; D005663:Furans; D009570:Nitriles