Issue 50, 2014

A water–ethanol on–off fiber catalyst for the synthesis of substituted 2-amino-2-chromenes

Abstract

A DMAP (4-dimethylaminopyridine) functionalized polyacrylonitrile fiber catalyst (PANDMAPF) was prepared and used to efficiently catalyze three-component condensation reactions among an aldehyde, malononitrile and α-naphthol in water to afford the corresponding substituted 2-amino-2-chromenes. The PANDMAPF exhibited excellent catalytic activities in water and methanol, but failed to show any catalytic activity in ethanol and solvents with low polarity. In other words, water can turn the reaction on but ethanol shuts it off. This differs greatly from the same reaction catalyzed by free DMAP or by a tertiary amine functionalized polyacrylonitrile fiber. The PANDMAPF catalyst is applicable to a wide range of aromatic aldehydes (80–99%). Moreover, this newly developed fiber catalyst also exhibited excellent recyclability and reusability (up to seven times) without any additional treatment.

Graphical abstract: A water–ethanol on–off fiber catalyst for the synthesis of substituted 2-amino-2-chromenes

Article information

Article type
Paper
Submitted
01 May 2014
Accepted
03 Jun 2014
First published
03 Jun 2014

RSC Adv., 2014,4, 26122-26128

Author version available

A water–ethanol on–off fiber catalyst for the synthesis of substituted 2-amino-2-chromenes

Y. Zhen, H. Lin, S. Wang and M. Tao, RSC Adv., 2014, 4, 26122 DOI: 10.1039/C4RA03985H

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