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Published on: June 21, 2017
Direct 2-Amination of Pyridines via Dearomatization/Rearomatization Strategy
Shuaiyu Chen1, Liujing Zhu1, Bingru Song1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua321004, China.
Abstract:
2-Aminopyridines are privileged scaffolds in pharmaceuticals, yet direct amination from pyridines remains scarce. We have developed a metal-free dearomatization/rearomatization strategy using readily available isocyanates as nitrogen source. Inexpensive DMAD serves as the dearomative reagent to form intermediates, which are rearomatized by DBU to afford 2-aminopyridines. The protocol offers good functional-group tolerance, operational simplicity, and scalability. It extends to quinolines and isoquinolines, and allows late-stage functionalization of complex biomolecules.
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