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.


Published in:
Journal of the American Chemical Society, 135, 12, 4708-4711
Year:
2013
Publisher:
Washington, Amer Chemical Soc
ISSN:
1520-5126
Laboratories:




 Record created 2013-04-09, last modified 2018-03-17


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