Synfacts 2009(4): 0379-0379  
DOI: 10.1055/s-0028-1087885
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Multisubstituted Pyridines from α-Diazocarbonyl Derivatives

Contributor(s): Victor Snieckus, Toni Rantanen
Z.-B. Chen, D. Hong, Y.-G. Wang*
Zhejiang University, Hangzhou, P. R. of China
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Publication History

Publication Date:
23 March 2009 (online)


A one-pot synthesis of substituted pyridines via a reaction of 2-azido-2,4-dienoates with α-diazocarbonyl compounds, both prepared via known procedures, in the presence of triphenylphosphine is reported. A plausible mechanistic scheme involves a Staudinger-Meyer reaction and a Wolff rearrangement of starting materials, combined together via an aza-Wittig reaction, the product of which undergoes an electrocyclic ring closure to afford the pyridines. A mechanism is proposed without evidence. The method seems to be efficient and general, as evidenced by the substrate scope and the high yields.