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Transition-Metal-Free Synthesis of Substituted Pyridines via Ring Expansion of 2-Allyl-2H-azirines

Yaojia Jiang, Cheol-Min Park* and Teck-Peng Loh*

*UNIST, UNIST-gil 50, Ulsan 689-798, Korea; School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore, Email: cmparkunist.ac.kr, teckpengntu.edu.sg

Y. Jiang, C.-M. Park, T.-P. Loh, Org. Lett., 2014, 16, 3432-3435.

DOI: 10.1021/ol501010k (free Supporting Information)


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Abstract

A DBU-promoted metal-free reaction of 2-allyl-2H-azirines affords 1-azatrienes that in situ electrocyclize to pyridines in very good yields. The reaction displays a broad substrate scope and tolerates various substituents. In addition, one-pot synthesis of pyridines from oximes via in situ formation of 2H-azirines was achieved.

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Key Words

pyridines


ID: J54-Y2014