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research article
Synthesis of Substituted Pyridines from Cascade [1 + 5] Cycloaddition of Isonitriles to
A novel strategy for de novo synthesis of pyridines featuring an unprecedented a-addition of aldehyde and enamide to isonitrile as a key step is described. Under mild conditions, a cascade reaction involving Zn(OTf)(2)-promoted [1 + 5] cycloaddition of isonitrile with N-formylmethyl-substituted enamide, facile aerobic oxidative aromatization and intermolecular acyl transfer from the pyridinium nitrogen to the 5-hydroxy oxygen, and finally acylation of the 4-amino group by an external acyl chloride efficiently afforded 2-substituted 4-acylamino-5-acyloxypyridines in good to excellent yields.
Type
research article
Web of Science ID
WOS:000317032000034
Authors
Publication date
2013
Publisher
Published in
Volume
135
Issue
12
Start page
4708
End page
4711
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
April 9, 2013
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