Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF<sub>2</sub>COONa for the Divergent Assembly of <i>N</i>-(Quinolin-2-yl)amides and Quinolin-2(1<i>H</i>)-ones
Yaquan Wang, Yao Zhou, Xingxing Ma, Qiuling Song
Abstract
Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
Topics & Concepts
ChemistrySynthonAlkyneProtonationReagentRitter reactionSolventCombinatorial chemistryIsocyanideMedicinal chemistryCatalysisNitrileOrganic chemistryIonCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Synthesis and Catalysis