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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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Publication details

The article was received on 08 Dec 2015, accepted on 07 Jan 2016 and first published on 07 Jan 2016


Article type: Communication
DOI: 10.1039/C5GC02935J
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Citation: Green Chem., 2016,18, 1855-1858
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    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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