Goulart Tales A C, Recchi Ana Maria S, Back Davi Fernando, Zeni Gilson
Laboratorio de Sintese, Reatividade, Avaliaçao Farmacologica e Toxicologica de Organocalcogenios, CCNE, UFSM, Santa Maria, Rio Grande do Sul, 97105-900, Brasil.
Laboratorio de Materiais Inorganicos, CCNE, UFSM, Santa Maria, Rio Grande do Sul, 97105-900, Brasil.
Org Biomol Chem. 2022 Jun 15;20(23):4773-4781. doi: 10.1039/d2ob00682k.
Organoselenyl iodide promoted the intramolecular nucleophilic cyclization of -alkynyl ethylcarbamates in the synthesis of 4-(organoselenyl) oxazolones. The reaction was regioselective, giving the five-membered oxazolone products as the unique regioisomer an initial activation of the carbon-carbon triple bond through a seleniranium intermediate, followed by an intramolecular 5- cyclization mode. The generality of the methodology has been proven by applying the optimized reaction conditions to different organoselenyl iodides and -alkynyl ethylcarbamates having different substituents directly bonded to the nitrogen atom and in the terminal position of the alkyne.
有机硒碘化物在4-(有机硒基)恶唑酮的合成中促进了α-炔基乙基氨基甲酸酯的分子内亲核环化反应。该反应具有区域选择性，生成的五元恶唑酮产物是唯一的区域异构体——通过硒鎓中间体对碳-碳三键进行初始活化，随后是分子内5-环化模式。通过将优化的反应条件应用于不同的有机硒碘化物和α-炔基乙基氨基甲酸酯，这些化合物在与氮原子直接相连以及炔烃末端位置具有不同的取代基，从而证明了该方法的通用性。
