Journal
ORGANIC LETTERS
Volume 16, Issue 13, Pages 3432-3435Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol501010k
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Funding
- Singapore Ministry of Education [MOE2011-T2-1-013, MOE2012-T2-1-014]
- National Environment Agency (NEA-ETRP) [1002 111]
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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. 1:22 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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