Synthesis of Thioureas, Thioamides, and Aza-Heterocycles via Dimethyl-Sulfoxide-Promoted Oxidative Condensation of Sulfur, Malonic Acids, and Amines - Archive ouverte HAL
Article Dans Une Revue Organic Letters Année : 2023

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

Résumé

Malonic acid and derivatives have been well known to undergo monodecarboxylation under relatively mild conditions and have been exclusively used as C2 synthon. We report herein their new application as C1 synthon via double decarboxylation promoted by sulfur and DMSO. In the presence of amines as nucleophiles, a wide range of thioureas and thioamides as well as Nheterocycles were obtained in good to excellent yields under mild heating conditions.

Domaines

Chimie organique
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Dates et versions

hal-04210733 , version 1 (19-09-2023)

Identifiants

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Trung Hieu Do, Supasorn Phaenok, Darunee Soorukram, Tina Modjinou, Daniel Grande, et al.. Synthesis of Thioureas, Thioamides, and Aza-Heterocycles via Dimethyl-Sulfoxide-Promoted Oxidative Condensation of Sulfur, Malonic Acids, and Amines. Organic Letters, 2023, 25 (34), pp.6322-6327. ⟨10.1021/acs.orglett.3c02247⟩. ⟨hal-04210733⟩
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