Salicylaldehyde-Promoted Cobalt-Catalyzed C–H/N–H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue
Mao‐Gui Huang, Shuai Shi, Ming Li, Yue‐Jin Liu, Ming‐Hua Zeng
Abstract
)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.
Topics & Concepts
SalicylaldehydeAnnulationChemistryCombinatorial chemistryCatalysisLigand (biochemistry)CobaltAntagonistStereochemistryReceptor antagonistMedicinal chemistryReceptorOrganic chemistrySchiff baseBiochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthesis of Indole Derivatives