Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF 2 COONa for the Divergent Assembly of N -(Quinolin-2-yl)amides and Quinolin-2(1 H )-ones

作者：Yaquan Wang, Yao Zhou, Xingxing Ma, Qiuling Song · 发表于：Organic Letters · 年份：2021 · DOI：10.1021/acs.orglett.1c01484 · 被引用次数：43 · 研究领域：Catalytic C–H Functionalization Methods、Catalytic Cross-Coupling Reactions、Asymmetric Synthesis and Catalysis

Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF 2 COONa to divergent construction of N -(quinolin-2-yl)amides and quinolin-2(1 H )-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF 2 COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF 2 COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.