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

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

102 Scopus citations

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
State	Published - 3 Jul 2014
Externally published	Yes

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title = "Transition-metal-free synthesis of substituted pyridines via ring expansion of 2-allyl-2H-azirines",

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}",

year = "2014",

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doi = "10.1021/ol501010k",

language = "英语",

volume = "16",

pages = "3432--3435",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Transition-metal-free synthesis of substituted pyridines via ring expansion of 2-allyl-2H-azirines

AU - Jiang, Yaojia

AU - Park, Cheol Min

AU - Loh, Teck Peng

PY - 2014/7/3

Y1 - 2014/7/3

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84903689092&partnerID=8YFLogxK

U2 - 10.1021/ol501010k

DO - 10.1021/ol501010k

M3 - 文章

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SN - 1523-7060

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SP - 3432

EP - 3435

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

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

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