[2 + 3] Annulative Coupling of Tetrahydroisoquinolines with Aryliodonio diazo compounds To Access 1,2,4-Triazolo[3,4-<i>a</i>]isoquinolines
Monish Arbaz Ansari, Shahnawaz Khan, Subhasish Ray, Gaurav Shukla, Maya Shankar Singh
Abstract
Base promoted one-pot annulative coupling of 1,2,3,4-tetrahydroisoquinolines (THIQs) with hypervalent iodine(III) species aryliodonio diazo compounds has been devised for the direct construction of 1,2,4-triazolo[3,4-a]isoquinoline derivatives at room temperature in open air for the first time. This approach involves [2 + 3] cascade annulation of nucleophilic THIQ with an electrophilic aryliodonio diazo compound via N–H and α-C1(sp3)–H difunctionalization of THIQ.
Topics & Concepts
ChemistryHypervalent moleculeIsoquinolineDiazoAnnulationElectrophileTetrahydroisoquinolineNucleophileBase (topology)Medicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryIodineCatalysisMathematicsMathematical analysisCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms