Synthesis of tetrahydropyrrolothiazoles through one-pot and four-component N,S-acetalation and decarboxylative [3+2] cycloaddition
Xiaoming Ma, Weiqi Qiu, Liu Li, Xiaofeng Zhang, JohnMark Awad, Jason Evans, Wei Zhang
Abstract
A four-component and one-pot synthesis involving N,S-acetalation of aldehydes with cysteine followed by the reaction with second aldehydes for decarboxylative [3 + 2] cycloaddition with maleimides is developed for stereoselective synthesis of tetrahydropyrrolothiazoles. High synthetic efficiency, using EtOH as solvent and catalyst, and only releasing CO2 and H2O as byproducts make this method favorable in green metrics analysis.
Topics & Concepts
CycloadditionStereoselectivityCatalysisComponent (thermodynamics)ChemistrySolventOrganic chemistryOne-pot synthesisDecarboxylationCombinatorial chemistryPhysicsThermodynamicsChemistry and Chemical EngineeringMulticomponent Synthesis of HeterocyclesChemical Synthesis and Reactions