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Issue 23, 2020
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Nitromethane as a surrogate cyanating agent: 7-N,N-dimethylamino-4-hydroxycoumarin-catalyzed, metal-free synthesis of α-iminonitriles

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Abstract

An efficient, metal/alkali-cyanide free approach for the synthesis of α-iminonitriles via kinetically controlled, base-mediated and 1,3-diketone-catalyzed reaction is reported. The preparation of target compounds was realized by condensation of substituted anilines and aldehydes in nitromethane as a surrogate cyanating agent and as a solvent. This strategy was further improved by replacing aldehydes and nitromethane with β-nitrostyrene and ethanol, respectively, rendering the methodology greener. The catalytic role played by 1,3-diketones such as 7-N,N-dimethylamino-4-hydroxycoumarin in this three-component reaction was investigated, and a plausible mechanism was proposed based on control experiments.

Graphical abstract: Nitromethane as a surrogate cyanating agent: 7-N,N-dimethylamino-4-hydroxycoumarin-catalyzed, metal-free synthesis of α-iminonitriles

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Article information


Submitted
10 Oct 2020
Accepted
02 Nov 2020
First published
03 Nov 2020

Green Chem., 2020,22, 8316-8322
Article type
Paper

Nitromethane as a surrogate cyanating agent: 7-N,N-dimethylamino-4-hydroxycoumarin-catalyzed, metal-free synthesis of α-iminonitriles

I. Satyanarayana, K. B. Manjappa and D. Yang, Green Chem., 2020, 22, 8316
DOI: 10.1039/D0GC03411H

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