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Domino synthesis of fully substituted pyridines by silver-catalyzed chemoselective hetero-dimerization of isocyanides

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Abstract

A silver-catalyzed hetero-dimerization of various vinyl isocyanides with isocyanoacetamides has been developed. This multistep domino reaction provides a facile protocol for the expedient synthesis of fully substituted pyridines in a single operation from readily available starting materials. An amidoketenimine and an azabutadienylketene are proposed as the key intermediates involved in this domino transformation. In addition, the resulting polysubstituted pyridines can be conveniently converted to pyridine-fused polycyclic frameworks.

Graphical abstract: Domino synthesis of fully substituted pyridines by silver-catalyzed chemoselective hetero-dimerization of isocyanides

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Article information


Submitted
02 Nov 2019
Accepted
19 Dec 2019
First published
23 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Domino synthesis of fully substituted pyridines by silver-catalyzed chemoselective hetero-dimerization of isocyanides

Z. Hu, M. Zhang, Q. Zhou, X. Xu and B. Tang, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01333D

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