Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from <i>N</i>-2-Nitrophenyl Hydrazonyl Bromides
作者:Mhairi Boyle、Keith Livingstone、Martyn C. Henry、Jessica M. L. Elwood、J. Daniel Lopez-Fernandez、Craig Jamieson
DOI:10.1021/acs.orglett.1c03993
日期:2022.1.14
rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance
我们报告了如何利用源自N -2-硝基苯基肼基溴的高反应性腈亚胺的重排来轻松构建酰胺键。发现该酰胺化反应广泛适用于伯、仲和叔酰胺的合成,是合成降脂剂苯扎贝特的关键步骤。这种方法的正交性和官能团耐受性以未受保护的氨基酸的N-酰化为例。