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Multi-component solvent-free cascade reaction of 2-cyanoacetamides with ketones and acetone: highly regioselective synthesis of functionalized pyridin-2-ones bearing quaternary centers

Ling-Bin Kong,   Rong Huang,   Hao-Dan He,   Yun-Xiang Fan,   Jun Lin  and  Sheng-Jiao Yan  

Abstract

A novel protocol has been constructed for the synthesis of four types of pyridin-2-ones (2−5) via a solvent-free cascade reaction of 2-cyanoacetamides 1, various ketones, and acetone via multicomponent reactions to prepare target compounds with good to excellent yields. As a result, functionalized pyridin-2-ones bearing quaternary centers (2-5), specifically, spiro pyridine-2-ones (3 and 5), which are promoted by piperdine under solvent-free conditions. Also, a double bond has been introduced into target compounds 4 and 5 only through the aryl substituted 2-cyanoacetamides under the same conditions. The advantages of this approach include no solvents, simple and practical operation (multi-component one-pot), high yields (up to 95%), and a product with potential biological activity.

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Publication details

The article was received on 28 Oct 2019, accepted on 24 Nov 2019 and first published on 25 Nov 2019


Article type: Paper
DOI: 10.1039/C9GC03692J
Green Chem., 2019, Accepted Manuscript

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    Multi-component solvent-free cascade reaction of 2-cyanoacetamides with ketones and acetone: highly regioselective synthesis of functionalized pyridin-2-ones bearing quaternary centers

    L. Kong, R. Huang, H. He, Y. Fan, J. Lin and S. Yan, Green Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9GC03692J

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