Base-promoted regioselective synthesis of 1,2,3,4-terahydroquinolines and quinolines from N-boc-3-piperidone |
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| Affiliation: | 1. Department of Chemistry, University of Delhi, North Campus, Delhi, 110007, India;2. Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Makkah, Saudi Arabia;1. Chemistry Department and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal;2. Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Paseo Senda del Rey, 9, E-28040 Madrid, Spain;3. Departamento de Cristalografía y Biología Estructural, Instituto de Química-Física Rocasolano, CSIC, Serrano, 119, E-28006 Madrid, Spain;4. Instituto de Química Médica, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain;5. Instituto de Ciencia y Tecnología de Polímeros, Juan de la Cierva, 3, E-28006 Madrid, Spain;1. Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi Arabia;2. Department of Chemistry Faculty of Science, Mansoura University, Mansoura, Egypt;3. Department of Chemistry, Faculty of Science, Tanta University, Tanta, Egypt;4. Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, Saudi Arabia;5. Department of Chemistry, Faculty of Applied Sciences, Taiz University, P.O. Box 82, Taiz, Yemen;1. Department of Chemistry, Ben-Gurion University of the Negev, 84105, Beer-Sheva, Israel;2. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Street, 664033, Irkutsk, Russian Federation;1. Department of Chemistry, Ben-Gurion University of the Negev, 84105, Beer-Sheva, Israel;2. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Street, 664033, Irkutsk, Russian Federation |
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| Abstract: | An efficient synthesis of 1,2,3,4-tetrahydroquinolines with donor and acceptor group has been delineated by base mediated ring transformation of 6-aryl-4-substituted-2H-pyran-2-one-3-carbonitriles by N-boc-3-piperidone followed by consecutive deprotection of Boc group under acidic conditions. This reaction involves 2 new bond formations namely C4a-C5 and C8a-C8 in order to create the nucleus. Various donor and acceptor functional groups like aryl, heteroaryl, nitrile, methylsulfanyl and secondary amine were installed in 1,2,3,4-tetrahydroquinolines. We extended our approach to synthesize the fused 1,2,3,4-tetrahydroquinolines by using 2-oxobenzo[h]chromenes as precursor. Further, we synthesized fused and isolated quinolines through aromatization of 1,2,3,4-tetrahydroquinolines by DDQ in excellent yields. Single-crystal X-ray analysis of the Boc protected tetrahydroisoquinoline 6t showed the steric hindrance between N-Boc and aryl group. |
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| Keywords: | 1,2,3,4-Tetrahydroquinolines Quinolines Base Deprotection |
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