Synthesis of Thioureas, Thioamides, and Aza-Heterocycles via Dimethyl-Sulfoxide-Promoted Oxidative Condensation of Sulfur, Malonic Acids, and Amines

Do T.H.Phaenok S.Soorukram D.Modjinou T.Grande D.Nguyen T.T.T.Nguyen T.B.Mahidol University2023-09-102023-09-102023-09-01Organic letters Vol.25 No.34 (2023) , 6322-6327https://repository.li.mahidol.ac.th/handle/20.500.14594/89587Malonic acid and derivatives have been well-known to undergo monodecarboxylation under relatively mild conditions and have been exclusively used as a C2 synthon. We report herein their new application as a C1 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.Biochemistry, Genetics and Molecular BiologySynthesis of Thioureas, Thioamides, and Aza-Heterocycles via Dimethyl-Sulfoxide-Promoted Oxidative Condensation of Sulfur, Malonic Acids, and AminesArticleSCOPUS10.1021/acs.orglett.3c022472-s2.0-851695038401523705237606344