Issue 34, 2023

Access to 2-pyridinones comprising enaminonitriles via AgOAc promoted cascade reactions of thioesters with aminomethylene malononitriles

Abstract

The facile synthesis of 2-pyridinones containing enaminonitriles from thioesters with aminomethylene malononitriles is achieved through an AgOAc-promoted acylation/cyclization/tautomerization cascade reaction. Control experiments reveal that AgOAc acts as a versatile promoter, activating both thioester and cyano groups while also serving as a Brønsted base in the cascade sequence. Moreover, 2-pyridinones were transformed into biologically significant 2-pyridinone-fused 2-pyrimidones with intriguing fluorescence emission properties.

Graphical abstract: Access to 2-pyridinones comprising enaminonitriles via AgOAc promoted cascade reactions of thioesters with aminomethylene malononitriles

Supplementary files

Article information

Article type
Communication
Submitted
08 Jun 2023
Accepted
17 Jul 2023
First published
17 Jul 2023

Org. Biomol. Chem., 2023,21, 6881-6885

Access to 2-pyridinones comprising enaminonitriles via AgOAc promoted cascade reactions of thioesters with aminomethylene malononitriles

C. Zhu, J. Zhou, T. Li, J. Yang, H. Jin and L. Zhang, Org. Biomol. Chem., 2023, 21, 6881 DOI: 10.1039/D3OB00915G

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