Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment
Qinghe Gao, Yimei Guo, Zhenhua Sun, Xiaodan He, Yiqiao Gao, Guangping Fan, Penghui Cao, Lizhen Fang, Suping Bai, Yanlong Jia
Abstract
With triethylamine as a vinylene source, a convenient protocol for the regioselective synthesis of β,γ-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been accomplished. The deaminative cyclization is also extended to long-chain tertiary alkylamines, enabling diverse alkyl groups to be concurrently installed into the pyridine rings. This process demonstrates a new conversion pathway for the simultaneous dual C(sp3)–H bond functionalization of tertiary amines, wherein the transient acyclic enamines generated in situ undergo the Povarov reaction.
Topics & Concepts
ChemistryFragment (logic)StereochemistryCombinatorial chemistryOrganic chemistryProgramming languageComputer scienceCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsChemical Synthesis and Analysis