College of Chemistry, Chemical Engineering and Materials Science of Soochow University, 199 Ren'ai Road, Suzhou, Jiangsu 215123, China.
Jiangsu Laboratory of Advanced Functional Material, School of Chemistry and Materials Engineering, Changshu Institute of Technology, Changshu 215500, China.
Molecules. 2019 Mar 29;24(7):1234. doi: 10.3390/molecules24071234.
The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C⁻H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C⁻N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.
由于其强导向能力，8-氨基喹啉（8-AQ）作为一种辅助试剂，已被广泛应用于 C⁻H 官能化反应中的酰胺化反应。本研究中，相应的 8-AQ 酰胺的简便温和的 Boc 保护对于通过扭转其几何形状降低酰胺共振能来激活酰胺 C⁻N 键至关重要。芳基和烷基胺在一锅法、用户友好的条件下进行酰胺交换反应，产率优异。
