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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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    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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    † Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
    ‡ Key Laboratory of Bioorganic Phosphorous and Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, China
    § Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland
    [email protected]
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    Cite this: J. Am. Chem. Soc. 2013, 135, 12, 4708–4711
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    https://doi.org/10.1021/ja401701x
    Published March 12, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    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.

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    Cite this: J. Am. Chem. Soc. 2013, 135, 12, 4708–4711
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