Bicyclic Amidine-Triggered Cyclization of <i>o</i>-Alkynylisocyanobenzenes: Synthesis of Lactam-Derived Quinolines
Zhuang Xiong, Chunmei Hu, Wenjian Zhu, Simin Wu, Dan Wang, Yang Liu, Jing Lin, Suqin Guo, Jia‐Qiang Wu, Xue-Tao Xu
Abstract
Efficient access to the synthesis of lactam-derived quinoline through a bicyclic amidine-triggered cyclization reaction from readily prepared o -alkynylisocyanobenzenes has been developed. The reaction was initiated by nucleophilic attack of the bicyclic amidines to o -alkynylisocyanobenzenes, subsequently with intramolecular cyclization to produce a DBU-quinoline-based amidinium salt, followed by hydrolysis to afford the lactam-derived quinoline in moderate to good yields.
Topics & Concepts
AmidineBicyclic moleculeQuinolineLactamChemistryNucleophileCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsChemical Synthesis and AnalysisAdvanced Synthetic Organic Chemistry