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
1. [1]
  M. Ló pez-García, I. Alfonso, V. Gotor. Synthesis of (R)-3, , 4-diaminobutanoic acid by desymmetrization of dimethyl 3-(benzylamino)glutarate through enzymatic ammonolysis[J]. J. Org. Chem., 2002,68:648-651.
2. [2]
  M. Ochiai, T. Okada, N. Tada, A. Yoshimura, K. Miyamoto, M. Shiro, Difluoro-λ3-bromane-induced Hofmann rearrangement of sulfonamides: synthesis of sulfamoyl fluorides, J. Am. Chem. Soc. 131 (2009) 8392-8393.
3. [3]
  A.B. Smith, I.G. Safonov, R.M. Corbett, Total syntheses of (+)-zampanolide and (+)-dactylolide exploitinga unifiedstrategy, J.Am.Chem.Soc.124(2002) 11102-11113.
4. [4]
  A. Carrë r, J.C. Florent, E. Auvrouin, P. Rousselle, E. Bertounesque. Synthesis of, 3-aryl-2-arylamidobenzofurans based on the curtius rearrangement[J]. J. Org. Chem., 2011,76:2502-2520. doi: 10.1021/jo102265b
5. [5]
  D.G. Hilmey, L.A. Paquette, Promoter-dependent course of the Beckmann rearrangement of stereoisomeric spiro[4.4]nonane-1, 6-dione monoximes, Org. Lett. 7 (2005) 2067-2069.
6. [6]
  Y. Furuya, K. Ishihara, H. Yamamoto. Cyanuric chloride as a mild and active Beckmann rearrangement catalyst[J]. J. Am. Chem. Soc., 2005,127:11240-11241. doi: 10.1021/ja053441x
7. [7]
  J.S. Kingsbury, E.J. Corey. Enantioselective total synthesis of isoedunol and β-araneosene featuring unconventional strategy and methodology[J]. J. Am. Chem. Soc., 2005,127:13813-13815. doi: 10.1021/ja055137+
8. [8]
  K. Suzuki, H. Takikawa, Y. Hachisu, J.W. Bode. Isoxazole-directed pinacol rearrangement: stereocontrolled approach to angular stereogenic centers[J]. Angew. Chem. Int. Ed., 2007,46:3252-3254. doi: 10.1002/(ISSN)1521-3773
9. [9]
  S. Braverman, M. Cherkinsky, E.V.K. Suresh Kumar, H.E. Gottlieb. Rearrangements of trihalomethyl ketones[J]. Tetrahedron, 2000,56:4521-4529. doi: 10.1016/S0040-4020(00) 00360-4
10. [10]
  A.S. Ionkin, W.J. Marshall, B.M. Fish. Highly sterically hindered olefins: a case of E- and Z-di-tert-butyl a, b-unsaturated acids[J]. Org. Lett., 2008,10:2303-2305. doi: 10.1021/ol800808g
11. [11]
  K. Andries, P. Verhasselt, J. Guillemont, H.W. Gohlmann, J.M. Neefs, H. Winkler, J. Van Gestel, P. Timmerman, M. Zhu, E. Lee, P. Williams, D. de Chaffoy, E. Huitric, S. Hoffner, E. Cambau, C. Truffot-Pernot, N. Lounis, V. Jarlier. A diarylquinoline drug active on the ATP synthase of mycobacterium tuberculosis[J]. Science, 2005,307:223-227. doi: 10.1126/science.1106753
12. [12]
  J. Guillemont, C. Meyer, A. Poncelet, X. Bourdrez, K. Andries, Diarylquinolines, synthesis pathways and quantitative structure-activity relationship studies leading to the discovery of TMC207, Future Med. Chem. 3 (2011) 1345-1360.
13. [13]
  A.Matteelli, A.C.C. Carvalho, K.E.Dooley, A. Kritski, TMC207: the first compound of a new class of potent anti-tuberculosis drugs, Future Microbiol. 5 (2010) 849-858.
14. [14]
  C.X. He, H. Meng, X. Zhang, H.Q. Cui, D.L. Yin. Synthesis and bio-evaluation of phenothiazine derivatives as new anti-tuberculosis agents[J]. Chin. Chem. Lett., 2015,26:951-954. doi: 10.1016/j.cclet.2015.03.027
15. [15]
  M. Yutaka, T. Sakae, N. Yoshiharu, H. Masatomo, Reactions of 3-substituted quinoline 1-oxides with acylating agents, Heterocycles 32 (1991) 1579-1586.
1. [1]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
2. [2]
  Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP₂/C anode with native oxidation PO_x component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
3. [3]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
4. [4]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
5. [5]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
6. [6]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
7. [7]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
8. [8]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
9. [9]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
10. [10]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
11. [11]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
12. [12]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
13. [13]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
14. [14]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
15. [15]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
16. [16]
  Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
17. [17]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
18. [18]
  Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
19. [19]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
20. [20]
  Yu Hong , Yuqian Jiang , Chenhuan Yuan , Decai Wang , Yimeng Sun , Jian Jiang . Unraveling temperature-dependent supramolecular polymorphism of naphthalimide-substituted benzene-1,3,5-tricarboxamide derivatives. Chinese Chemical Letters, 2024, 35(12): 109909-. doi: 10.1016/j.cclet.2024.109909

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(748)
HTML views(18)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142