Citation: Di Hu, Chao Pi, Wei Hu, Xiliang Han, Yangjie Wu, Xiuling Cui. Ru(Ⅲ)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources[J]. Chinese Chemical Letters, ;2022, 33(8): 4064-4068. doi: 10.1016/j.cclet.2021.12.072 shu

Ru(Ⅲ)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources

Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450052, China

pichao@zzu.edu.cn

cuixl@zzu.edu.cn

Received Date: 20 November 2021
Revised Date: 24 December 2021
Accepted Date: 26 December 2021
Available Online: 1 January 2022

Figures(6)

A Ru(Ⅲ)-catalyzed annulation reaction of 2-aminoaromatic aldehydes (ketones) and isoxazoles to afford diverse 3-cyanoquinolines has been developed. Notably, isoxazole acted as a cyclization reagent and nontoxic cyano source via N-O bond cleavage and fragmentation. Variously substituted (especially 6- or 7-substituted) quinolines could be easily afforded. This procedure features wide functional group compatibility, efficiency and avoiding toxic cyano source. Meanwhile, this protocol could be successfully applied to scale-up synthesis. Further chemical transformations of 3-cyanoquinoline could give some valuable skeletons, demonstrating its potential in synthetic application
- Isoxazoles,
- Cyclization reagent,
- Cyano sources,
- Variously substituted 3-cyanoquinolines
1. [1]
  X.X. Yu, P. Zhao, Y. Zhou, et al., J. Org. Chem.86 (2021) 8381-8388. doi: 10.1021/acs.joc.1c00793
2. [2]
  Y. Gao, S. Yang, Y. Huo, et al., ACS Catal. 11 (2021) 7772-7779. doi: 10.1021/acscatal.1c02055
3. [3]
  K. Nakatani, S. Sando, I. Saito, Bioorg. Med. Chem. Let. 9 (2001) 2381-2385. doi: 10.1016/S0968-0896(01)00160-2
4. [4]
  C.L. Chiang, C.F. Shu, Chem. Mater. 14 (2002) 682-687. doi: 10.1021/cm010665f
5. [5]
  J. Li, E. Tan, N. Keller, et al., J. Am. Chem. Soc. 141 (2019) 98-103. doi: 10.1021/jacs.8b11466
6. [6]
  J.K. Natarajan, J.N. Alumasa, K. Yearick, et al., J. Med. Chem. 51 (2008) 3466-3479. doi: 10.1021/jm701478a
7. [7]
  V.R. Solomon, H. Lee, Curr. Med. Chem. 18 (2011) 1488-1508. doi: 10.2174/092986711795328382
8. [8]
  A. Çapcı, M.M. Lorion, H. Wang, et al., Angew. Chem. Int. Ed. 58 (2019) 13066-13079. doi: 10.1002/anie.201907224
9. [9]
  Y. Hsiao, N.R. Rivera, N. Yasuda, D.L. Hughes, P.J. Reider, Org. Lett. 3 (2001) 1101-1103. doi: 10.1021/ol006785v
10. [10]
  E. W. C. ohn, J. Am. Chem. Soc. 52 (1930) 3685-3688. doi: 10.1021/ja01372a038
11. [11]
  A. Weyesa, E. Mulugeta, RSC Adv. 10 (2020) 20784-20793. doi: 10.1039/d0ra03763j
12. [12]
  H.R. Tsou, E.G. Overbeek-Klumpers, W.A. Hallett, et al., J. Med. Chem. 48 (2005) 1107-1131. doi: 10.1021/jm040159c
13. [13]
  H. Jallal, M.L. Valentino, G. Chen, et al., Cancer Res. 67 (2007) 1580-1588. doi: 10.1158/0008-5472.CAN-06-2027
14. [14]
  D. Laheru, G. Croghan, R. Bukowski, et al., Clin. Cancer Res. 14 (2008) 5602-5609. doi: 10.1158/1078-0432.CCR-08-0433
15. [15]
  R. Roskoski Jr, Pharmacol. Res. 144 (2019) 19-50. doi: 10.1016/j.phrs.2019.03.006
16. [16]
  A. Ardestani, S. Li, K. Annamalai, et al., Nat. Commun. 10 (2019) 5015. doi: 10.1038/s41467-019-12880-5
17. [17]
  E.C. Taylor Jr, N.W. Kalenda, J. Am. Chem. Soc. 78 (1956) 5108-5115. doi: 10.1021/ja01600a079
18. [18]
  S. Lv, Y. Li, T. Yao, et al., Org. Lett. 20 (2018) 4994-4997. doi: 10.1021/acs.orglett.8b01952
19. [19]
  B.K. Sarmah, M. Konwar, D. Bhattacharyya, P. Adhikari, A. Das, Adv. Synth. Catal. 361 (2019) 5616-5625. doi: 10.1002/adsc.201901103
20. [20]
  H. Xu, Y. Zhu, X. Chai, J. Yang, L. Dong, Green Synth. Catal. 1 (2020) 167-170. doi: 10.1016/j.gresc.2020.09.001
21. [21]
  J.J. Neumann, M. Suri, F. Glorius, Angew. Chem. Int. Ed. 49 (2010) 7790-7794. doi: 10.1002/anie.201002389
22. [22]
  M. Suri, T. Jousseaume, J.J. Neumann, F. Glorius, Green Chem. 14 (2012) 2193-2196. doi: 10.1039/c2gc35476d
23. [23]
  J. Kuang, B. Chen, S. Ma, Org. Chem. Front. 1 (2014) 186-189. doi: 10.1039/C4QO00007B
24. [24]
  D.S. Treitler, S. Leung, M. Lindrud, Org. Process Res. Dev. 21 (2017) 460-467. doi: 10.1021/acs.oprd.7b00016
25. [25]
  F. Brosge, J.F. Kochs, M. Bregu, et al., Org. Lett. 22 (2020) 6667-6670. doi: 10.1021/acs.orglett.0c02504
26. [26]
  S. Du, Z. Yang, J. Tang, Z. Chen, X.F. Wu, Org. Lett. 23 (2021) 2359-2363. doi: 10.1021/acs.orglett.1c00568
27. [27]
  J. Lindley, Tetrahedron. 40 (1984) 1433-1456. doi: 10.1016/S0040-4020(01)91791-0
28. [28]
  R. Gerber, M. Oberholzer, C.M. Frech, Chem. Eur. J. 18 (2012) 2978-2986. doi: 10.1002/chem.201102936
29. [29]
  S. Pimparkar, A. Koodan, S. Maiti, et al., Chem. Common. 57 (2021) 2210-2232. doi: 10.1039/d0cc07783f
30. [30]
  T.D. Senecal, W. Shu, S.L. Buchwald, Angew. Chem. Int. Ed. 52 (2013) 10035-10039. doi: 10.1002/anie.201304188
31. [31]
  M. Barbero, S. Cadamuro, S. Dughera, Org. Biomol. Chem. 14 (2016) 1437-1441. doi: 10.1039/C5OB02321A
32. [32]
  X.J. Wang, S.L. Zhang, New J. Chem. 41 (2017) 14826-14830. doi: 10.1039/C7NJ03405A
33. [33]
  J. Zanon, A. Klapars, S.L. Buchwald, J. Am. Chem. Soc. 125 (2003) 2890-2891. doi: 10.1021/ja0299708
34. [34]
  C. Yang, J.M. Williams, Org. Lett. 6 (2004) 2837-2840. doi: 10.1021/ol049621d
35. [35]
  P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev. 40 (2011) 5049-5067. doi: 10.1039/c1cs15004a
36. [36]
  H. Yu, R.N. Richey, W.D. Miller, J. Xu, S.A. May, J. Org. Chem. 76 (2011) 665-668. doi: 10.1021/jo102037y
37. [37]
  G. Giachi, M. Frediani, W. Oberhauser, F. Lamaty, J. Martinez, E. Colacino, ChemSusChem 7 (2014) 919-924. doi: 10.1002/cssc.201300997
38. [38]
  T. Chatterjee, R. Dey, B.C. Ranu, J. Org. Chem. 79 (2014) 5875-5879. doi: 10.1021/jo500820q
39. [39]
  F. Burg, J. Egger, J. Deutsch, N. Guimond, Org. Process Res. Dev. 20 (2016) 1540-1545. doi: 10.1021/acs.oprd.6b00229
40. [40]
  L.R. Mills, J.M. Graham, P. Patel, S.A.L. Rousseaux, J. Am. Chem. Soc. 141 (2019) 19257-19262. doi: 10.1021/jacs.9b11208
41. [41]
  Z. Shu, Y. Ye, Y. Deng, Y. Zhang, J. Wang, Angew. Chem. Int. Ed. 52 (2013) 10573-10576. doi: 10.1002/anie.201305731
42. [42]
  L. Wang, G. Wang, J. Zhang, et al., Nat. Commun. 8 (2017) 15240. doi: 10.1038/ncomms15240
43. [43]
  S. Sayama, Heterocycles 92 (2016) 1796-1802. doi: 10.3987/COM-16-13542
44. [44]
  U. Dutta, D.W. Lupton, D. Maiti, Org. Lett. 18 (2016) 860-863. doi: 10.1021/acs.orglett.6b00147
45. [45]
  T. Delcaillau, P. Boehm, B. Morandi, J. Am. Chem. Soc. 143 (2021) 3723-3728. doi: 10.1021/jacs.1c00529
46. [46]
  M.P. Moon, A.P. Komin, J.K. Wolfe, G.F. Morris, J. Org. Chem. 48 (1983) 2392-2399. doi: 10.1021/jo00162a020
47. [47]
  M. Tanaka, Y. Abe, K. Tokuyama, Chem. Pharm. Bull. 26 (1978) 1558-1569. doi: 10.1248/cpb.26.1558
48. [48]
  P. Charpentier, V. Lobrégat, V. Levacher, et al., Tetrahedron Lett. 39 (1998) 4013-4016. doi: 10.1016/S0040-4039(98)00677-7
49. [49]
  D.K. O'Dell, K.M. Nicholas, J. Org. Chem. 68 (2003) 6427-6430. doi: 10.1021/jo034447c
50. [50]
  N. Kondo, H. Umetani, Jpn. Kokai Tokkyo Koho JP 2013237647.
51. [51]
  N. Kondo, H. Umetani, Jpn. Kokai Tokkyo Koho JP 2013237648.
52. [52]
  Y. Zhang, T. Zhang, H. Zhan, X. Li, Chin. J. Catal. 35 (2014) 1840-1845.
53. [53]
  W.X. Wang, Q.Z. Zhang, T.Q. Zhang, et al., Adv. Synth. Catal. 357 (2015) 221-226. doi: 10.1002/adsc.201400637
54. [54]
  G.E. Davico, J. Phys. Org. Chem. 18 (2005) 434-440. doi: 10.1002/poc.879
55. [55]
  C.M. Nunes, I. Reva, T.M.V.D. Pinho e Melo, et al., J. Am. Chem. Soc. 133 (2011) 18911-18923. doi: 10.1021/ja207717k
56. [56]
  J. Velcicky, A. Soicke, R. Steiner, H.G. Schmalz, J. Am. Chem. Soc. 133 (2011) 6948-6951. doi: 10.1021/ja201743j
57. [57]
  J. Wu, J. Liu, K. Zhou, et al., Chem. Common. 56 (2020) 12660-12663. doi: 10.1039/d0cc05439a
58. [58]
  P.E. Simm, P. Sekar, J. Richardson, P.W. Davies, ACS Catal. 11 (2021) 6357-6362. doi: 10.1021/acscatal.1c01457
59. [59]
  J. Ren, C. Pi, Y. Wu, X. Cui, Org. Lett. 21 (2019) 4067-4071. doi: 10.1021/acs.orglett.9b01246
60. [60]
  T. Wan, C. Pi, Y. Wu, X. Cui, Org. Lett. 22 (2020) 6484-6488. doi: 10.1021/acs.orglett.0c02283
61. [61]
  Y. He, C. Pi, Y. Wu, X. Cui, Chin. Chem. Lett. 31 (2020) 396-400.
62. [62]
  Y. Wu, C. Pi, Y. Wu, X. Cui, Chem. Soc. Rev. 50 (2021) 3677-3689. doi: 10.1039/d0cs00966k
63. [63]
  J.M. Knapp, A.B. Wood, P.W. Phuan, et al., J. Med. Chem. 55 (2012) 1242-1251. doi: 10.1021/jm201372q
64. [64]
  H. Maezaki, M. Tawada, T. Yamashita, et al., Bioorg. Med. Chem. Let. 27 (2017) 3565-3571.
65. [65]
  J. Ren, X. Yan, X. Cui, et al., Green Chem. 22 (2020) 265-269. doi: 10.1039/c9gc03567b
66. [66]
  J.Y. Chen, Y.W. Lin, W.M. He, Chin. Chem. Lett. 31 (2020) 2989-2990.
67. [67]
  S. Rieckhoff, M. Titze, W. Frey, R. Peters, Org. Lett. 19 (2017) 4436-4439. doi: 10.1021/acs.orglett.7b01895
68. [68]
  K. Okamoto, A. Nanya, A. Eguchi, K. Ohe, Angew. Chem. Int. Ed. 57 (2018) 1039-1043. doi: 10.1002/anie.201710920
69. [69]
  Y. Ge, W. Sun, B. Pei, et al., Org. Lett. 20 (2018) 2774-2777. doi: 10.1021/acs.orglett.8b00971
70. [70]
  S.S. Giri, R.S. Liu, ACS Catal. 9 (2019) 7328-7334. doi: 10.1021/acscatal.9b02323
71. [71]
  L. Li, F. Han, X. Nie, et al., Angew. Chem. Int. Ed. 59 (2020) 12392-12395. doi: 10.1002/anie.202004243
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