A domino reaction of alpha,beta-acetylenic gamma-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; Oleg A Dyachenko

doi:10.1021/ol1011532

A domino reaction of alpha,beta-acetylenic gamma-hydroxy nitriles with arenecarboxylic acids: an unexpected facile shortcut to 4-cyano-3(2H)-furanones

Org Lett. 2010 Jul 16;12(14):3200-3. doi: 10.1021/ol1011532.

Authors

Boris A Trofimov¹, Olesya A Shemyakina, Anastasiya G Mal'kina, Igor' A Ushakov, Olga N Kazheva, Grigorii G Alexandrov, Oleg A Dyachenko

Affiliation

¹ 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

PMID: 20536165
DOI: 10.1021/ol1011532

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Carboxylic Acids / chemistry*
Furans / chemistry*
Nitriles / chemistry*

Substances

Alkynes
Carboxylic Acids
Furans
Nitriles