Issue 6, 2014

Group-assisted purification (GAP) chemistry for dihydrofurans: water as a medium for catalyst free synthesis in a one pot four component reaction

Abstract

A simple, catalyst free, water mediated, one pot four component, green protocol was developed for title compounds 7 starting from aromatic aldehydes (1), malononitrile (2), 1,3-diones (3) and N-chlorosuccinimide (NCS) in a sequential addition reaction at ambient temperature. The approach presented herein, for the first time, is through an unusual rearrangement where NCS was reacted with 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (4), which was formed by the Knoevenagel condensation of aldehyde and malononitrile followed by the Michael addition of 3. In addition, this novel protocol is compatible with various aldehydes and active C–H functional derivatives, accomplishes high yields and follows the GAP chemistry principle. Interestingly, compound 4 when reacted with NCS in alcohol medium gave 2-cyano-6,6-dimethyl-4-oxo-3-aryl-2,3,4,5,6,7-hexahydrobenzofuran-2-carboxylate (5).

Graphical abstract: Group-assisted purification (GAP) chemistry for dihydrofurans: water as a medium for catalyst free synthesis in a one pot four component reaction

Supplementary files

Article information

Article type
Paper
Submitted
05 Mar 2014
Accepted
02 Apr 2014
First published
02 Apr 2014

Green Chem., 2014,16, 3237-3246

Group-assisted purification (GAP) chemistry for dihydrofurans: water as a medium for catalyst free synthesis in a one pot four component reaction

M. Chennapuram, N. R. Emmadi, C. Bingi, J. B. Nanubolu and K. Atmakur, Green Chem., 2014, 16, 3237 DOI: 10.1039/C4GC00388H

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