18036-88-9Relevant academic research and scientific papers
N-Atom Deletion in Nitrogen Heterocycles
Qin, Haitao,Cai, Wangshui,Wang, Shuang,Guo, Ting,Li, Guigen,Lu, Hongjian
, p. 20678 - 20683 (2021/08/25)
Excising the nitrogen in secondary amines, and coupling the two residual fragments is a skeletal editing strategy that can be used to construct molecules with new skeletons, but which has been largely unexplored. Here we report a versatile method of N-atom excision from N-heterocycles. The process uses readily available N-heterocycles as substrates, and proceeds by N-sulfonylazidonation followed by the rearrangement of sulfamoyl azide intermediates, providing various cyclic products. Examples are provided of deletion of nitrogen from natural products, synthesis of chiral O-heterocycles from commercially available chiral β-amino alcohols, formal inert C?H functionalization through a sequence of N-directed C?H functionalization and N-atom deletion reactions in which the N-atom can serve as a traceless directing group.
