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Synfacts 2012; 8(3): 0309
DOI: 10.1055/s-0031-1290218
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Tandem One-Pot Synthesis of Polysubstituted Pyridines

Contributor(s):
Paul Knochel
,
Christoph Sämann
Chun YS, Lee JH, Kim JH, Ko YO, Lee S.-g * Ewha Womans University, Seoul, Korea
Tandem One-Pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-Enynes.

Org. Lett. 2011;
13: 6390-6393
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Further Information

Publication History

Publication Date:
20 February 2012 (online)

 
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Key words

polysubstituted pyridines - tandem one-pot reaction - zinc

Significance

An efficient tandem one-pot process has been developed for the synthesis of polysubstituted pyridines with complete control of substitution patterns. The tandem reaction proceeds via the regio- and chemoselective addition of the Blaise reaction intermediate to the 1,3-enyne followed by an isomerization–cyclization–aromatization process.


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Comment

This convenient and straightforward process is characterized by high yields and its good functional group tolerance. The method described is very versatile due to various substitution patterns of the pyridine ring that can be generated.


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