Chalkidis Savvas G, Hong Sungil, Tsiadi Anthi-Markella, Fika Evangelia, Tsoureas Nikolaos, Mpourmpakis Giannis, Vougioukalakis Georgios C
Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece.
Department of Chemical and Petroleum Engineering, University of Pittsburgh, Pittsburgh, Pennsylvania 15261, United States.
J Org Chem. 2025 Mar 28;90(12):4302-4312. doi: 10.1021/acs.joc.5c00020. Epub 2025 Mar 19.
A base-catalyzed protocol is reported for the construction of 1,3-thiazolidine-2-thione scaffolds bearing quaternary carbon centers from carbon disulfide and α-tertiary propargylamines. The reaction proceeds using low catalyst loading, under ambient temperatures, and in the absence of solvent. Various α-tertiary propargylamines have been employed, affording a series of previously unreported thiazolidine-2-thione compounds and avoiding purification via column chromatography in certain cases. We also describe a one-pot strategy for the synthesis of the same products through a KA coupling-CS incorporation approach. The reaction mechanism and substituent-dependent catalytic behavior were studied through a combination of detailed experimental and computational studies.
报道了一种碱催化的方法，用于从二硫化碳和α-叔炔丙胺构建带有季碳中心的1,3-噻唑烷-2-硫酮骨架。该反应在环境温度下、低催化剂负载量且无溶剂的条件下进行。使用了各种α-叔炔丙胺，得到了一系列以前未报道的噻唑烷-2-硫酮化合物，并且在某些情况下避免了柱色谱纯化。我们还描述了一种通过KA偶联-CS引入方法一锅合成相同产物的策略。通过详细的实验和计算研究相结合，研究了反应机理和取代基依赖性催化行为。
