Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 12, Pages 4708-4711Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja401701x
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Funding
- National Natural Science Foundation of China
- Tsinghua University
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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.
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