Asymmetric synthesis of 2-arylpiperazines |
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| Affiliation: | 1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan;2. Interdisciplinary Program for Biomedical Sciences, Institute for Academic Initiatives, Osaka University, 1-1 Yamadaoka, Suita, Osaka 565-0871, Japan;1. Photosens, Université de Lorraine, SRSMC UMR7565, F-54506 Vandoeuvre-Lès-Nancy, France;2. Photosens, CNRS, SRSMC UMR7565, F-54506 Vandoeuvre-Lès-Nancy, France;3. (ISOF-CNR c/o) Department of Chemical and Pharmaceutical Sciences, University of Ferrara, Via Luigi Borsari 46, 44121 Ferrara, Italy;1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Ulitsa Vavilova, dom 28, Moscow 119991, Russia;2. Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Technical University of Lisbon, Av. Rovisco Pais, 1049-001 Lisbon, Portugal;3. Semenov Institute of Chemical Physics, Russian Academy of Sciences, Ulitsa Kosygina, dom 4, Moscow 119991, Russia;1. Boreskov Institute of Catalysis, Lavrentieva Ave 5, Novosibirsk 630090, Russian Federation;2. Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russian Federation;1. Department of Chemistry, Oakland University, Rochester, MI 48309-4477, USA;2. Department of Chemistry, University at Buffalo, State University of New York, Buffalo, NY 14260-3000, USA;3. Department of Chemistry, University of Rochester, Rochester, NY 14627-0216, USA;1. Department of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Sakaka, Aljouf 72341, Saudi Arabia;2. College of Pharmacy, Dongguk University-Seoul, Goyang 10326, Republic of Korea;3. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;4. Chemical Kinomics Research Center, Korea Institute of Science and Technology (KIST), Seoul 02792, Republic of Korea;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo P.O. Box 11562, Egypt;6. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, New Giza University, New giza, km 22, Cairo–Alexandria Desert Road, Cairo, Egypt;7. Division of Bio-Medical Science & Technology, KIST School, Korea University of Science and Technology, Seoul 02792, Republic of Korea;8. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kafrelsheikh University, Kafrelsheikh, Egypt;9. Department of Pharmaceutical Organic Chemistry, Beni-Suef University, Beni-Suef 62514, Egypt;10. Department of Orthopedics and Traumatology, Faculty of Medicine, Mansoura University, Mansoura 35516, Egypt;11. Clinical Pharmacy Department, College of Pharmacy, Jouf University, Sakaka, Aljouf 72341, Saudi Arabia;12. Department of Pharmacology, College of Pharmacy, Jouf University, Sakaka, Aljouf 72341, Saudi Arabia |
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| Abstract: | An asymmetric synthesis of 2-arylpiperazines starting from phenacyl bromides, a variety of which are easily available, has been established. The synthesis features a CBS reduction of phenacyl bromide to provide optically enriched compounds, an SN2 reaction of 1,2,3-oxathiazolidine 2-oxides with an azide anion with invert of configuration, and construction of the piperazine ring via reduction of piperazine-2,3-diones. |
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| Keywords: | Asymmetric synthesis Heterocycles Piperazines |
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