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J Am Chem Soc. 2013 Mar 27;135(12):4708-11. doi: 10.1021/ja401701x. Epub 2013 Mar 14.

Synthesis of substituted pyridines from cascade [1 + 5] cycloaddition of isonitriles to N-formylmethyl-substituted enamides, aerobic oxidative aromatization, and acyl transfer reaction.

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  • 1Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Abstract

A novel strategy for de novo synthesis of pyridines featuring an unprecedented α-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.

PMID:
23477427
[PubMed - indexed for MEDLINE]
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