Dichloroimidazolidinedione-Activated Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
Yu Gao, Jingjing Liu, Zhenjiang Li, Tianfo Guo, Songquan Xu, Hui Zhu, Fulan Wei, Siming Chen, Hailemariam Gebru and Kai Guo*
*State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, China, Email: guoknjtech.edu.cn
Y. Gao, J. Liu, Z. Li, T. Guo, S. Xu, H. Zhu, F. Wei, S. Chen, H. Gebru, K. Guo, J. Org. Chem., 2018, 83, 2040-2049.
Substoichiometric amounts of the readily available and economical geminal dichloroimidazolidinediones (DCIDs) enable an activation of the Beckmann rearrangement via a unique self-propagating mechanism. 23 rearrangements have been performed with excellent yields in a short time, including a substrate for synthesizing the monomer of nylon-12 and a complicated steroidal substrate on a preparative scale.
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