Catalyst-free inverse-electron-demand aza-Diels-Alder reaction of 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes: access to polysubstituted tetrahydropyridines

An inverse-electron-demand aza-Diels-Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes under catalyst-free and additive-free conditions was developed, which provided a highly convenient and straightforward method to construct a series of polyfunctionalized tetrahydrop...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-07, Vol.21 (26), p.5413-5418
Main Authors: Yang, Dezhi, Zhu, Meng, Wang, Taimin, He, Yixuan, Xie, Lang, Zhang, Jiayong, Cheng, Bin
Format: Article
Language:English
Subjects:
Catalysts
Diels-Alder reactions
Functional groups
Substrates
Tetrahydropyridines
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Summary:An inverse-electron-demand aza-Diels-Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes under catalyst-free and additive-free conditions was developed, which provided a highly convenient and straightforward method to construct a series of polyfunctionalized tetrahydropyridines in high yields. This strategy features numerous advantages, including high efficiency, good functional group tolerance, broad substrate scope, and environmentally friendly conditions. An inverse-electron-demand aza-Diels-Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes under catalyst-free and additive-free conditions was developed.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00511a