Jiang Yaojia, Park Cheol-Min, Loh Teck-Peng
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637616, Singapore.
Org Lett. 2014 Jul 3;16(13):3432-5. doi: 10.1021/ol501010k. Epub 2014 Jun 20.
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.
报道了一种在无金属条件下通过1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）促进打开2-烯丙基-2H-氮杂环丙烷生成1-氮杂三烯的新策略，该1-氮杂三烯可原位电环化生成吡啶，产率良好至优异。该反应底物范围广泛，对包括芳基、烷基和杂环基在内的各种取代基具有良好的耐受性。此外，还实现了通过肟原位形成2H-氮杂环丙烷一锅法合成吡啶。
