Preparation of Thioamide Building Blocks via Microwave-Promoted Three-Component Kindler Reactions
2002; American Chemical Society; Volume: 5; Issue: 2 Linguagem: Inglês
10.1021/cc0200538
ISSN1520-4774
AutoresOleksandr I. Zbruyev, Nikola Stiasni, C. Oliver Kappe,
Tópico(s)Synthesis of heterocyclic compounds
ResumoA microwave-enhanced variation of the Kindler thioamide synthesis is introduced. Taking advantage of the sealed vessel capabilities of a dedicated single-mode microwave reacto,r a diverse selection of 13 aldehyde and 12 amine precursors was utilized in the construction of a representative 34-member library of substituted thioamides. The three-component condensations of aldehydes, amines, and elemental sulfur were carried out using 1-methyl-2-pyrrolidone (NMP) as solvent employing microwave flash heating at 110−180 °C for 2−20 min. A simple workup protocol allows the isolation of synthetically valuable primary, secondary, and tertiary thioamide building blocks in 83% average yield and >90% purity.
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