Synthesis of 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro- 1,6-naphthyridines by a directed lithiation reaction |
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| Institution: | 1. The Key Laboratory of Major Autoimmune Diseases, Anhui Province, Anhui Institute of Innovative Drugs, School of Pharmacy, Anhui Medical University, Hefei, China;2. The Key Laboratory of Anti-inflammatory of Immune Medicines, Ministry of Education, Hefei, China;3. Institute for Liver Diseases of Anhui Medical University, Hefei, China;1. Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang, 110016, China;2. Key Laboratory of Receptors-Mediated Gene Regulation and Drug Discovery, School of Medicine, Henan University, Kaifeng, 475004, China;3. The School of life Science and Biopharmaceutical, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang, 110016, China;1. Discovery Research, Mochida Pharmaceutical Co. Ltd., 722 Uenohara, Jimba, Gotemba, Shizuoka 412-8524, Japan;2. Department of Structural Chemistry, Merck Research Laboratories, Merck and Co., Inc., 2000 Galloping Hill Road, Kenilworth, NJ 07033, USA;3. Department of Medicinal Chemistry, Merck Research Laboratories, Merck and Co., Inc., 2000 Galloping Hill Road, Kenilworth, NJ 07033, USA;1. Medicinal Chemistry, Oncology, IMED Biotech Unit, AstraZeneca, Cambridge CB4 0WG, United Kingdom;2. Northern Institute for Cancer Research, Chemistry, School of Natural and Environmental Sciences, Bedson Building, Newcastle University, Newcastle upon Tyne NE1 7RU, United Kingdom |
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| Abstract: | N-(tert-butoxycarbonyl)anilines (7), are easily converted in a one pot reaction sequence into the N- (tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinolines (8), by directed ortho lithiation followed by reaction with 1- chloro-3-iodopropane, hence providing a new versatile quinoline ring nucleus synthesis. In an analogous reaction 2-N-(tert-butoxycarbonyl)- and an 2-N-(pivaloylamino) pyridine are converted to 1,2,3,4-tetrahydro-1,6- naphthyridines. |
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