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Park, Cheol-Min
Synthetic & Medicinal Chemistry Lab
Research Interests
  • Organic synthesis, medicinal chemistry, chemical biology

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Transition-metal-free synthesis of substituted pyridines via ring expansion of 2-allyl-2H-azirines

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Title
Transition-metal-free synthesis of substituted pyridines via ring expansion of 2-allyl-2H-azirines
Author
Jiang, YaojiaPark, Cheol-MinLoh, Teck-Peng
Keywords
HIGHLY FUNCTIONALIZED PYRIDINES; DE-NOVO SYNTHESIS; H BOND AMINATION; 2+2+2 CYCLOADDITION; MULTICOMPONENT REACTIONS; REGIOSELECTIVE SYNTHESIS; DIELS-ALDER; 2H-AZIRINES; DERIVATIVES; CHEMISTRY
Issue Date
201407
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v.16, no.13, pp.3432 - 3435
Abstract
A new strategy to open the 2-allyl-2H-azirines by 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) promotion in metal-free conditions affording 1-azatrienes that in situ electrocyclize to the pyridines in good to excellent yields is reported. The reaction displays a broad substrate scope and good tolerance to a variety of substituents including aryl, alkyl, and heterocyclic groups. In addition, one-pot synthesis of pyridines from oximes via in situ formation of 2H-azirines was achieved.
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DOI
http://dx.doi.org/10.1021/ol501010k
ISSN
1523-7060
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