Acid-promoted metal-free synthesis of 3-ketoquinolines from amines,enaminones and DMSO |
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| Institution: | 1. School of Life Sciences, Anhui Agricultural University, Hefei 230036, PR China;2. Department of Applied Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, PR China;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, PR China;1. Department of Pharmaceutical and Pharmacological Sciences, University of Padova, via Marzolo 5, 35131 Padova, Italy;2. Fondazione per la Biologia e la Medicina della Rigenerazione T.E.S.—Tissue Engineering and Signalling Onlus, Via F. Marzolo 13, 35131 Padova, Italy;1. Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, PR China;2. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China;1. School of Pharmacy, China Medical University, Taichung, Taiwan;2. The Ph.D. Program for Cancer Biology and Drug Discovery, China Medical University and Academia Sinica, Taichung, Taiwan;3. Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC, USA;4. Agricultural Biotechnology Research Center, Academia Sinica, Taipei, Taiwan;5. Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung, Taiwan;1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, 160 062, Punjab, India;2. Department of Pharmaceutical Technology (Biotechnology), National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, 160 062, Punjab, India;3. Department of Pharmacology and Toxicology, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, 160 062, Punjab, India;4. Indo-Soviet Friendship (ISF) College of Pharmacy, Moga, 142 001, Punjab, India;1. College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, PR China;2. Zhejiang Provincial People’s Hospital, People’s Hospital of Hangzhou Medical College, Hangzhou 310014, PR China |
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| Abstract: | A metal-free p-toluenesulfonic acid (TsOH·H2O) mediated synthesis of 3-ketoquinolines from anilines, enaminones and DMSO has been developed. In this transformation, DMSO was activated by TsOH·H2O and provided the one-carbon unit of the 3-ketoquinolines. A plausible mechanism involving an electrophilic sulfenium ion intermediate was proposed. |
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| Keywords: | Enaminones DMSO One carbon synthon 3-Ketoquinolines |
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