10.1007/s10593-010-0647-2
The study focuses on the intramolecular cyclization of 1-[1-alkylsulfanyl-2-phenyl-2-(phenylhydrazono)ethylidene]pyrrolidinium salts, which are synthesized by the alkylation of thioamide with benzyl, allyl, and propargylsulfanyl groups in the presence of cesium carbonate in DMF at room temperature. These pyrrolidinium salts can be efficiently converted into 1,3-diphenyl-6,7,8,8a-tetrahydro-1H-pyrrolo[2,1-c]-1,2,4-triazine-4-thione derivatives in good yields. The research demonstrates that this cyclization method is general for alkyl derivatives of arylhydrazonothioacetamides, expanding the scope of this reaction type. The synthesized pyrrolotriazines are of practical interest due to their potential high antitumor activity, making them promising candidates for biological investigation. The study was financially supported by the Russian Basic Research Fund and includes detailed experimental procedures, characterization data, and comparison of the reaction outcomes with different bases and solvents.
10.1016/j.tetlet.2013.03.114
The study presents the first Pd-catalyzed α-arylation of thioamides, exploring their use in coupling chemistry as carbon nucleophiles for transition-metal-catalyzed C–C coupling reactions. Thioamides, which contain sulfur, nitrogen, and an α-carbon as adjacent nucleophilic centers, are significant synthetic building blocks. In this research, a variety of α-arylated thioamides were synthesized in moderate to good yields under mild conditions, offering a new synthetic transformation for thioamides and an alternative method to access functionalized thioamides. Key chemicals used include N,N-dimethyl-3-phenylpropanethioamide (thioamide 1a), iodobenzene (aryl halide 2a), and [Pd(C3H5)Cl]2 (a palladium catalyst), along with phosphine ligand PPh3. These chemicals served to facilitate the coupling reaction, with the palladium catalyst playing a crucial role in the C–C bond formation, and the phosphine ligand enhancing the reaction's efficiency. The study also demonstrated high chemoselectivity for thioamides over amides in the reaction.
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