COS-triggered oxygen/sulfur exchange of isatins: chemoselective synthesis of functionalized isoindigos and spirothiopyrans <i>via</i> self-condensation and the thio-Diels–Alder reaction
Wei Chen, Hui Zhou, Bai‐Hao Ren, Wei‐Min Ren, Xiao‐Bing Lu
Abstract
the thio-Diels-Alder reaction. Mechanistic studies with experimental and density functional theory approaches revealed that the O/S ER between isatins and COS results in the formation of 3-thioisatins as the key intermediates, which further undergo solvent-controlled transformations to generate isoindigos or spirothiopyrans, respectively. The easily-accessible substrates and operational simplicity make the process suitable for further exploration. The practicality of this transformation was demonstrated by the gram-scale synthesis of isoindigo-based drug molecules and donor-acceptor conjugated polymers.
Topics & Concepts
ChemistryThio-Conjugated systemReagentSulfurCombinatorial chemistrySolventCondensation reactionChemoselectivityMoleculeDensity functional theoryOrganic chemistryPolymerCatalysisComputational chemistryQuinazolinone synthesis and applicationsSulfur-Based Synthesis TechniquesMulticomponent Synthesis of Heterocycles