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Issue 7, 2016
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Chemical cascades in water for the synthesis of functionalized aromatics from furfurals

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Abstract

One-pot synthetic routes from furfurals to polysubstituted aromatic compounds have been developed in water, without the need for any organic solvents. The reaction proceeds via an uncatalysed, one-pot reaction cascade through formation of a hydrazone derivative, in situ cycloaddition with a dienophile, then aromatisation. A range of substituted phthalimides can be accessed with complete control over the substitution pattern. The reaction was also extended to other dienophiles and the diene 2-furylacrolein. The phthalimide products were further elaborated to produce a variety of polysubstituted benzenes including pharmaceutically relevant compounds.

Graphical abstract: Chemical cascades in water for the synthesis of functionalized aromatics from furfurals

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Supplementary files

Article information


Submitted
08 Dec 2015
Accepted
07 Jan 2016
First published
07 Jan 2016

This article is Open Access

Green Chem., 2016,18, 1855-1858
Article type
Communication
Author version available

Chemical cascades in water for the synthesis of functionalized aromatics from furfurals

S. Higson, F. Subrizi, T. D. Sheppard and H. C. Hailes, Green Chem., 2016, 18, 1855
DOI: 10.1039/C5GC02935J

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