Issue 8, 2018

Triflic acid-catalyzed metal-free synthesis of (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones

Abstract

A TfOH-catalyzed highly efficient synthesis of biologically active (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones has been reported with 64–94% yields under metal-free conditions. The reaction proceeds through sequential Knoevenagel condensation/stereoselective in situ monohydration of nitrile or C–N cyclization protocol in one-pot. The attractive features of this tandem process are moderate reaction conditions, high atom economy, broad substrate scope, gram-scale reaction and ease of operation.

Graphical abstract: Triflic acid-catalyzed metal-free synthesis of (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones

Supplementary files

Article information

Article type
Paper
Submitted
08 Jan 2018
Accepted
14 Mar 2018
First published
15 Mar 2018

New J. Chem., 2018,42, 6433-6440

Triflic acid-catalyzed metal-free synthesis of (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones

B. D. Rupanwar, S. S. Chavan, A. M. Shelke and G. M. Suryavanshi, New J. Chem., 2018, 42, 6433 DOI: 10.1039/C7NJ05169G

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