一种基于狄尔斯-阿尔德反应的广泛适用的氯胺酮相关芳基环己胺的合成方法。
A Broadly Applicable Diels-Alder-Based Synthesis of Ketamine-Related Arylcyclohexylamines.
作者信息
Weber Henrik, Drouvé Nils, Kortenbrede Lana, El Sheikh Sherif
机构信息
Faculty of Applied Natural Sciences, Cologne University of Applied Sciences, Campusplatz 1, 51379 Leverkusen, Germany.
出版信息
J Org Chem. 2023 Aug 4;88(15):11372-11376. doi: 10.1021/acs.joc.3c01226. Epub 2023 Jul 18.
Herein, we report the synthesis of aryl derivatives of ketamine and of ketamine's major metabolites hydroxynorketamine (HNK), norketamine (NK), and dehydronorketamine (DHNK) via a microwave-assisted Diels-Alder reaction to form the substituted cyclohexane core structure. Starting with aryl acrylic esters as dienophiles and siloxybutadienes as diene counterparts, a wide range of substituted arylcyclohexylamines was obtained after several modification steps of the initial Diels-Alder products [El Sheikh, S.; Weber, H.; Kortenbrede, L.; Drouvé, N. A broadly applicable Diels-Alder based Synthesis of Ketamine related Arylcyclohexylamines. 2022, 10.26434/chemrxiv- 2022-xf1l9].
在此，我们报告了通过微波辅助的狄尔斯-阿尔德反应合成氯胺酮及其主要代谢物羟基去甲氯胺酮（HNK）、去甲氯胺酮（NK）和脱氢去甲氯胺酮（DHNK）的芳基衍生物，以形成取代的环己烷核心结构。以芳基丙烯酸酯作为亲双烯体，硅氧基丁二烯作为双烯体，在最初的狄尔斯-阿尔德产物经过几个修饰步骤后，得到了一系列取代的芳基环己胺[El Sheikh, S.; Weber, H.; Kortenbrede, L.; Drouvé, N. 基于狄尔斯-阿尔德反应的氯胺酮相关芳基环己胺的广泛适用合成方法。2022, 10.26434/chemrxiv - 2022 - xf1l9]。
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