功能化不对称乙烯基二硫化物的简便合成及其逆电子需求杂环狄尔斯-阿尔德反应
Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction.
作者信息
Jędrzejewski Bartosz, Musiejuk Mateusz, Doroszuk Justyna, Witt Dariusz
机构信息
Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland.
出版信息
Materials (Basel). 2021 Mar 10;14(6):1342. doi: 10.3390/ma14061342.
The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of -vinyl phosphorodithioate with thiotosylates or -vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities such as hydroxy, carboxy, protected amino, or ester groups. Vinyl disulfides reacted with the generated transient -iminothioquinones in an inverse electron-demand [4+2] cycloaddition to produce benzo[][1,4]thiazine derivatives.
设计了在温和条件下以中等到高收率制备带有额外官能团的不对称乙烯基二硫化物的简单、方便且高效的方法。所开发的方法包括乙烯基二硫代磷酸酯与硫代甲苯磺酸酯的反应，或乙烯基硫代甲苯磺酸酯与硫醇的反应。所设计的方法能够合成带有诸如羟基、羧基、保护氨基或酯基等额外官能团的不对称乙烯基二硫化物。乙烯基二硫化物与生成的瞬态亚氨基硫代醌发生逆电子需求的[4+2]环加成反应，生成苯并[][1,4]噻嗪衍生物。
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