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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A Broadly Applicable Diels-Alder-Based Synthesis of Ketamine-Related Arylcyclohexylamines
Henrik Weber1, Nils Drouvé1, Lana Kortenbrede1
1Faculty of Applied Natural Sciences, Cologne University of Applied Sciences, Campusplatz 1, 51379 Leverkusen, Germany.
Abstract:
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. ChemRxiv 2022, 10.26434/chemrxiv- 2022-xf1l9].
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