DNA-Compatible Synthesis of Thiazolidione Derivatives via Three-Component Annulation and Knoevenagel Condensation
Yiting Wang, Xianfu Fang, Huilin Liao, Gong Zhang, Yangfeng Li, Yizhou Li
Abstract
Thiazolidione, conferring drug-like properties, is an important heterocycle that widely exists in medicinally relevant molecules. In this work, by efficiently assembling various DNA-tagged primary amines, abundant aryl isothiocyanates, and ethyl bromoacetate, we present a DNA-compatible three-component annulation to generate a 2-iminothiazolidin-4-one scaffold, which was further decorated via Knoevenagel condensation by employing (hetero)aryl and alkyl aldehydes. These thiazolidione derivatives should find broad use in focused DNA-encoded library construction.
Topics & Concepts
Knoevenagel condensationChemistryAnnulationCombinatorial chemistryArylAlkylComponent (thermodynamics)DNAMoleculeEthyl bromoacetateOrganic chemistryBiochemistryCatalysisPhysicsThermodynamicsChemical Synthesis and AnalysisClick Chemistry and ApplicationsSulfur-Based Synthesis Techniques