J Org Chem 2021 Sep 21. Epub 2021 Sep 21.
Institut UTINAM - UMR CNRS 6213, Université Bourgogne Franche-Comté, 16 Route de Gray, 25030 Besançon, France.
An efficient diastereoselective route is developed to get access to novel spiropyrrolo[1,2-]isoquinoline-oxindole skeletons by a -component [3 + 2] cycloaddition reaction of ()-5-arylidene-1,3-thiazolidine-2,4-diones, isatin derivatives, and 1,2,3,4-tetrahydroisoquinoline (THIQ). Interestingly, the regioselectivity of the reaction is both temperature- and solvent-dependent, allowing the synthesis of two regioisomeric -dispiropyrrolo[2,1-]isoquinolineoxindoles in excellent yield. Unprecedentedly, each isomeric dispiropyrrolo[2,1-]isoquinolineoxindole endured 1,3-dipolar cycloaddition/recycloaddition reactions under thermal or catalytic conditions to regenerate the corresponding regioisomeric counterpart. Read More