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Synthesis of polysubstituted pyridines from oxime acetates using NH4I as a dual-function promoter

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Abstract

Pyridine formation with oxime acetates as the building blocks under metal-free conditions is described. Ammonium iodide has proved to be a highly efficient promoter for oxime N–O bond reduction and subsequent condensation reactions, whereby it played a dual-function role in the transformation. While the three-component reaction of oxime acetates, benzaldehydes, and 1,3-dicarbonyls proceeded well with the assistance of a stoichiometric amount of ammonium iodide, the condensation of oximes and acroleins was enabled by using a catalytic initiator to afford substituted pyridines. By this protocol, substituted pyridine products were generated in moderate to excellent yields with tolerance towards a broad range of functional groups.

Graphical abstract: Synthesis of polysubstituted pyridines from oxime acetates using NH4I as a dual-function promoter

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Publication details

The article was received on 05 Oct 2017, accepted on 27 Nov 2017 and first published on 27 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02471A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis of polysubstituted pyridines from oxime acetates using NH4I as a dual-function promoter

    Y. Xia, J. Cai, H. Huang and G. Deng, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02471A

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