Citation: Chun-Xian He, Zhi-Bo Jiang, Hua-Qing Cui, Da-Li Yin. A nucleophilic 1, 3-rearrangement leading to 3, 4-disubstituted 3, 4-dihydroquinolines[J]. Chinese Chemical Letters, ;2016, 27(7): 1036-1039. doi: 10.1016/j.cclet.2016.02.030 shu

A nucleophilic 1, 3-rearrangement leading to 3, 4-disubstituted 3, 4-dihydroquinolines

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

Corresponding author: Da-Li Yin, yindali@imm.ac.cn
Received Date: 9 December 2015
Revised Date: 3 February 2016
Accepted Date: 18 February 2016
Available Online: 14 July 2016

Figures(6)

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.
- 1, 3-Rearrangement,
- Dihydroquinoline derivatives,
- Reaction mechanism
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沈阳化工大学材料科学与工程学院沈阳 110142