Synthesis of Thioureas, Thioamides, and Aza-Heterocycles via Dimethyl-Sulfoxide-Promoted Oxidative Condensation of Sulfur, Malonic Acids, and Amines
Trung Hieu, Supasorn Phaenok, Darunee Soorukram, Tina Modjinou, Daniel Grande, Thi Thanh Tam Nguyen, Thanh Bình Nguyễn
Abstract
Malonic acid and derivatives have been well-known to undergo monodecarboxylation under relatively mild conditions and have been exclusively used as a C 2 synthon. We report herein their new application as a C 1 synthon via double decarboxylation promoted by sulfur and dimethyl sulfoxide. In the presence of amines as nucleophiles, a wide range of thioureas and thioamides as well as N -heterocycles were obtained in good to excellent yields under mild heating conditions.
Topics & Concepts
ChemistrySynthonMalonic acidDecarboxylationSulfurDimethyl sulfoxideOxidative decarboxylationNucleophileOrganic chemistrySulfoxideCondensationCatalysisThermodynamicsPhysicsSynthesis of heterocyclic compoundsSynthesis and Reactivity of Sulfur-Containing CompoundsQuinazolinone synthesis and applications