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A nucleophilic 1,3-rearrangement leading to 3,4-disubstituted 3,4-dihydroquinolines |
Chun-Xian Hea, Zhi-Bo Jianga, Hua-Qing Cuib, Da-Li Yina |
a State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China;
b Department of Medicinal Chemistry, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China |
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Abstract A new nucleophilic 1,3-rearrangement is observed when treating 2-methoxyquinolino-3-lithium with an α-C substituted deoxybenzoin, and this rearrangement yielded an unusual 3,4-disubstituted 3,4-dihydroquinoline. Several similar reactions were designed and executed to investigate this novel 1,3-rearrangement, and a mechanism involving a nucleophilic addition and a following 1,3-rearrangement with an unusual dearomatization on the quinoline ring is proposed.
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Received: 09 December 2015
Published: 14 March 2016
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Fund:We are grateful to “The National High-Tech Research and Development Program (“863”Program) of China” ([2_TD$DIF]No. 2012AA020302) for financial support. |
Corresponding Authors:
Da-Li Yin
E-mail: yindali@imm.ac.cn
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