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

Yaojia Jiang; Cheol Min Park; Teck Peng Loh

doi:10.1021/ol501010k

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

Yaojia Jiang, Cheol Min Park^*, Teck Peng Loh

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

102 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3432-3435
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	13
DOIs	https://doi.org/10.1021/ol501010k
Publication status	Published - Jul 3 2014
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Yaojia Jiang and Park, {Cheol Min} and Loh, {Teck Peng}",

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doi = "10.1021/ol501010k",

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AU - Park, Cheol Min

AU - Loh, Teck Peng

PY - 2014/7/3

Y1 - 2014/7/3

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

Abstract

ASJC Scopus Subject Areas

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