An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
Wengang Wu,
Jun Yi,
Huipeng Xu,
Shuangjun Li,
Rongxin Yuan
Affiliations
Wengang Wu
College of Chemistry, Chemical Engineering and Materials Science of Soochow University, 199 Ren’ai Road, Suzhou, Jiangsu 215123, China
Jun Yi
Jiangsu Laboratory of Advanced Functional Material, School of Chemistry and Materials Engineering, Changshu Institute of Technology, Changshu 215500, China
Huipeng Xu
Jiangsu Laboratory of Advanced Functional Material, School of Chemistry and Materials Engineering, Changshu Institute of Technology, Changshu 215500, China
Shuangjun Li
Jiangsu Laboratory of Advanced Functional Material, School of Chemistry and Materials Engineering, Changshu Institute of Technology, Changshu 215500, China
Rongxin Yuan
Jiangsu Laboratory of Advanced Functional Material, School of Chemistry and Materials Engineering, Changshu Institute of Technology, Changshu 215500, China
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(acyl)–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.
