Citation: Xin Huang, Yingying Xu, Jianglian Li, Ruizhi Lai, Yi Luo, Qiantao Wang, Zhongzhen Yang, Yong Wu. Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate[J]. Chinese Chemical Letters, ;2021, 32(11): 3518-3521. doi: 10.1016/j.cclet.2021.04.058 shu

Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

zhongzhenyang1991@163.com

wyong@scu.edu.cn

Received Date: 4 March 2021
Revised Date: 22 April 2021
Accepted Date: 30 April 2021
Available Online: 7 May 2021

Figures(7)

A new strategy is developed for the synthesis of 1-aminoisoquinoline derivatives. This Rh(Ⅲ)-catalyzed [4 + 2] annulation reaction employs benzamidines as efficient directing groups and the vinylene carbonate as an acetylene surrogate. Additionally, the reaction features broad substrate scopes and good yields, only producing carbonate anion as byproduct.
- Benzamidamide,
- Aminoisoquinolines,
- Vinylene carbonate,
- C−H Activation,
- Rh-catalyzed
1. [1]
  A. Baccalini, G. Faita, G. Zanoni, D. Maiti, Chem. Eur. J.26 (2020) 9749-9783 doi: 10.1002/chem.202001832
2. [2]
  L. Song, E.V. Van der Eycken, Chem. Eur. J. 26 (2020) 1-25 doi: 10.1111/cwe.12349
3. [3]
  M.R. Sk, S.S. Bera, S. Basuli, A. Metya, M.S. Maji, Asian J. Org. Chem. 9 (2020) 1701-1717 doi: 10.1002/ajoc.202000367
4. [4]
  X. Huang, S. Liao, L. Xin, F. Zhang, Y. Yu, Synthesis 53 (2021) 238-254 doi: 10.1055/s-0040-1707268
5. [5]
  Z. Wang, P. Xie, Y. Xia, Chin. Chem. Lett. 2018, 29, 47-53 doi: 10.11648/j.ajmsp.20180303.12
6. [6]
  X. Han, P. Lin, Q. Li, Chin. Chem. Lett. 30 (2019) 1495-1502 doi: 10.1016/j.cclet.2019.04.027
7. [7]
  Y.F. Wang, K.K. Toh, J.Y. Lee, S. Chiba, Angew. Chem. Int. Ed. 50 (2011) 5927-5931 doi: 10.1002/anie.201101009
8. [8]
  R. Lai, X. Wu, S. Lv, et al., Chem. Commun. 55 (2019) 4039-4042 doi: 10.1039/c9cc01146c
9. [9]
  X. Chen, M. Wang, X. Zhang, X. Fan, Org. Lett. 21 (2019) 2541-2545 doi: 10.1021/acs.orglett.9b00340
10. [10]
  Y. Xu, X. Yang, X. Zhou, L. Kong, X. Li, Org. Lett. 19 (2017) 4307-4310 doi: 10.1021/acs.orglett.7b01974
11. [11]
  B. Ramesh, M. Tamizmani, M.J. Jeganmohan, J. Org. Chem. 84 (2019) 4058-4071 doi: 10.1021/acs.joc.9b00051
12. [12]
  S.T. Mei, H.W. Liang, B. Teng, et al., Org. Lett. 18 (2016) 1088-1091 doi: 10.1021/acs.orglett.6b00197
13. [13]
  L. Shi, B. Wang, Org. Lett. 18 (2016) 2820-2823 doi: 10.1021/acs.orglett.6b01234
14. [14]
  R. Chen, S. Cui, Org. Lett. 19 (2017) 4002-4005 doi: 10.1021/acs.orglett.7b01728
15. [15]
  X. Wu, H. Xiong, S. Sun, J. Cheng, Org. Lett. 20 (2018) 1396-1399 doi: 10.1021/acs.orglett.8b00119
16. [16]
  C. Zhou, J. Zhao, W. Guo, J. Jiang, J. Wang, Org. Lett. 21 (2019) 9315-9319 doi: 10.1021/acs.orglett.9b03357
17. [17]
  W. Chen, F.X. Liu, W. Gong, et al., Adv. Synth. Catal. 360 (2018) 2470-2475 doi: 10.1002/adsc.201800322
18. [18]
  D. Li, N. Xu, Y. Zhang, L. Wang, Chem. Commun. 50 (2014) 14862-14865 doi: 10.1039/C4CC06457G
19. [19]
  Y. Wang, H. Zhou, K. Xu, M. Shen, H. Xu, Chin. Chem. Lett. 28 (2017) 92-96 doi: 10.1117/12.2285263
20. [20]
  L. Wang, D. Xiong, L. Jie, C. Yu, X. Cui, Chinese Chem. Lett. 29 (2018) 907-910 doi: 10.1016/j.cclet.2018.05.007
21. [21]
  H. Li, Y. Han, Z. Yang, Z. Yao, L. Wang, X. Cui, Chin. Chem. Lett. 32 (2021) 1263–1266 doi: 10.1016/j.cclet.2020.09.020
22. [22]
  Y. Yu, Z. Xia, Q. Wu, D. Liu, L. Yu, Y. Xiao, Z. Tan, Deng, W.; Zhu, G., Chinese Chem. Lett. 32 (2021) 1263-1266 doi: 10.1016/j.cclet.2020.09.020
23. [23]
  J. Zhang, J.S. Sun, Y.Q. Xia, L. Dong, Adv. Synth. Catal. 361 (2019) 2037-2041 doi: 10.1002/adsc.201801606
24. [24]
  K. Muralirajan, R. Kuppusamy, S. Prakash, C.H. Cheng, Adv. Synth. Catal. 358 (2016) 774-783 doi: 10.1002/adsc.201501056
25. [25]
  C.E. Gutteridge, M.M. Hoffman, A.K. Bhattacharjee, W.K. Milhous, L. Gerena, Bioorg. Med. Chem. Lett. 21 (2011) 786-789 doi: 10.1016/j.bmcl.2010.11.099
26. [26]
  R. Saari, J. C. Torma, T. Nevalainen, Bioorg. Med. Chem. 19, (2011) 939-950 doi: 10.1016/j.bmc.2010.11.059
27. [27]
  A.L. Smith, F.F. DeMorin, N.A. Paras, et al., J. Med. Chem. 52 (2009) 6189-6192 doi: 10.1021/jm901081g
28. [28]
  N. Shelach, N. Lowenton-spier, Patent WO 2020165755 A1, 2020.
29. [29]
  C. Rivalle, F. Wendling, P. Tambourin, et al., J. Med. Chem. 26 (1983) 181-185 doi: 10.1021/jm00356a012
30. [30]
  C.G. Barber, R.P. Dickinson, P.V. Fish, Bioorg. Med. Chem. Lett. 14 (2004) 3227-3230 doi: 10.1016/j.bmcl.2004.03.094
31. [31]
  I.H. Bae, J.B. Son, S.M. Han, et al., Patent WO 2013100632, 2013.
32. [32]
  D.N. Rao, S. Rasheed, S. Aravinda, R.A. Vishwakarma, P. Das, RSC Adv. 3 (2013) 11472-11475 doi: 10.1039/c3ra40735g
33. [33]
  B.K. Lee, M.R. Biscoe, S.L. Buchwald, Tetrahedron Lett. 50 (2009) 3672-3674 doi: 10.1016/j.tetlet.2009.03.137
34. [34]
  C. Yang, F. Zhang, G.J. Deng, H. Gong, J. Org. Chem. 84 (2019) 181-190 doi: 10.1021/acs.joc.8b02588
35. [35]
  X. Xie, T.Y. Zhang, Z. Zhang, J. Org. Chem. 71 (2006) 6522-6529 doi: 10.1021/jo060945k
36. [36]
  D. Kim, P. Ghosh, N.Y. Kwon, et al., J. Org. Chem. 85 (2020) 2476-2485 doi: 10.1021/acs.joc.9b03173
37. [37]
  X. Chen, X. Li, Z. Qu, et al., Adv. Synth. Catal. 356 (2014) 1979-1985 doi: 10.1002/adsc.201301065
38. [38]
  W.Z. Bi, K. Sun, C. Qu, et al., Org. Chem. Front. 4 (2017) 1595-1600 doi: 10.1039/C7QO00311K
39. [39]
  Y. Nanaji, S. Kirar, S.V. Pawar, A.K. Yadav, RSC Adv. 10 (2020) 7628-7634 doi: 10.1039/c9ra10397j
40. [40]
  M. Couturier, L. Caron, S. Tumidajski, K. Jones, T. D. White, Org. Lett. 8 (2006) 1929-1932 doi: 10.1021/ol060473w
41. [41]
  A.T. Londregan, S. Jennings, W. Liuqing, Org. Lett. 12 (2010) 5254-5257 doi: 10.1021/ol102301u
42. [42]
  P.J. Manley, M.T. Bilodeau, Org. Lett. 4 (2002) 3127-3129 doi: 10.1021/ol0264556
43. [43]
  L.Y. Xie, S. Peng, L.L. Jiang, et al., Org. Chem. Front. 6 (2019) 167-171 doi: 10.1039/c8qo01128a
44. [44]
  S. Huang, H. Li, X. Sun, et al., Org. Lett. 21 (2019) 5570-5574 doi: 10.1021/acs.orglett.9b01902
45. [45]
  Y. Li, C. Jia, H. Li, et al., Org. Lett. 20 (2018) 4930-4933 doi: 10.1021/acs.orglett.8b02057
46. [46]
  Y. Li, Z. Qi, H. Wang, X. Yang, X. Li, Angew. Chem. Int. Ed. 55 (2016) 11877-11881 doi: 10.1002/anie.201606316
47. [47]
  Z. Qi, S. Yu, X. Li, Org. Lett. 18 (2016) 700-703 doi: 10.1021/acs.orglett.5b03669
48. [48]
  X. Song, Q. Zhou, J. Zhao, et al., Org. Lett. 22 (2020) 9506-9512 doi: 10.1021/acs.orglett.0c03515
49. [49]
  F. Xu, Y. Song, W. Zhu, et al., Chem. Commun. 56 (2020) 11227-11230 doi: 10.1039/d0cc04885b
50. [50]
  L. Xu, L. Wang, Y. Feng, et al., Org. Lett. 19 (2017) 4343-4346 doi: 10.1021/acs.orglett.7b02028
51. [51]
  J. Zhou, J. Li, Y. Li, et al., Org. Lett. 20 (2018) 7645-7649 doi: 10.1021/acs.orglett.8b03383
52. [52]
  X. Zhou, Z. Qi, S. Yu, et al., Adv. Synth. Catal. 359 (2017) 1620-1625 doi: 10.1002/adsc.201601278
53. [53]
  J. Ren, Y. Huang, C. Pi, X. Cui, Y. Wu, Chin. Chem. Lett. 32 (2021) 2592–2596. doi: 10.1016/j.cclet.2021.02.061
54. [54]
  J. Li, Z. Zhang, M. Tang, X. Zhang, J. Jin, Org. Lett. 18 (2016) 3898-3901 doi: 10.1021/acs.orglett.6b01916
55. [55]
  Y. Zuo, X. He, Y. Ning, Y. Wu, Y. Shang, J. Org. Chem. 83 (2018) 13463-13472 doi: 10.1021/acs.joc.8b02286
56. [56]
  J. Li, M. Tang, L. Zang, et al., Org. Lett. 18 (2016) 2742-2745 doi: 10.1021/acs.orglett.6b01199
57. [57]
  Q. Yang, C. Wu, J. Zhou, et al., Org. Chem. Front. 6 (2019) 393-398 doi: 10.1039/c8qo01148f
58. [58]
  C. Li, H.B. Xu, J. Zhang, M. Liu, L. Dong, Org. Biomol. Chem. 18 (2020) 1412-1416 doi: 10.1039/c9ob02553g
59. [59]
  J. Li, M. John, L. Ackermann, Chem. Eur. J. 20 (2014) 5403-5408 doi: 10.1002/chem.201304944
60. [60]
  X. Wei, M. Zhao, Z. Du, X. Li, Org. Lett. 13 (2011) 4636-4639 doi: 10.1021/ol2018505
61. [61]
  G. Zheng, M. Tian, Y. Xu, X. Chen, X. Li, Org. Chem. Front. 5 (2018) 998-1002 doi: 10.1039/C7QO01033H
62. [62]
  C. Wu, J. Zhou, G. He, et al., Org. Chem. Front. 6 (2019) 1183-1188 doi: 10.1039/c9qo00048h
63. [63]
  K. Ghosh, Y. Nishii, M. Miura, ACS Catal. 9 (2019) 11455-11460 doi: 10.1021/acscatal.9b04254
64. [64]
  K. Ghosh, Y. Nishii, M. Miura, Org. Lett. 22 (2020) 3547-3550 doi: 10.1021/acs.orglett.0c00975
65. [65]
  Y. Nishii, M. Miura, ACS Catal. 10 (2020) 9747-9757 doi: 10.1021/acscatal.0c02972
66. [66]
  Z.H. Wang, H. Wang, H. Wang, L. Li, M.D. Zhou, Org. Lett. 23 (2021) 995-999 doi: 10.1021/acs.orglett.0c04200
67. [67]
  X. Li, T. Huang, Y. Song, et al., Org. Lett. 22 (2020) 5925-5930 doi: 10.1021/acs.orglett.0c02016
68. [68]
  G. Mihara, K. Ghosh, Y. Nishii, M. Miura, Org. Lett. 22 (2020) 5706-5711 doi: 10.1021/acs.orglett.0c02112
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