Synthesis of 8‐Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups |
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Authors: | Hye Kyung Kim Prof. Dr. Seth R. Marder Prof. Dr. Sukbok Chang |
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Affiliation: | 1. School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332‐0400 (USA);2. Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 305‐701 (Korea);3. Department of Chemistry, Korea Advanced Institute of Science & Technology (KAIST), Daejeon 305‐701 (Korea) |
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Abstract: | Described herein is the development of practical routes to 8‐aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII‐catalyzed conditions: i) the use of pre‐generated chlorocarbamates and ii) a two‐step one‐pot process that directly employs carbamates. Both approaches are highly convenient for the gram‐scale synthesis of 8‐aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd‐catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N‐oxides, thus yielding 8‐aminoquinolines in excellent overall efficiency. |
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Keywords: | 8‐aminoquinolines amidating reagents carbamates C H activation homogeneous catalysis rhodium |
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