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.
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沈阳化工大学材料科学与工程学院沈阳 110142