Citation: Mei-Hua Shen, Chen Li, Qing-Song Xu, Bin Guo, Rui Wang, Xiaoqian Liu, Hua-Dong Xu, Defeng Xu. Allylation and alkylation of oxindoleketimines via imine umpolung strategy[J]. Chinese Chemical Letters, ;2021, 32(7): 2313-2316. doi: 10.1016/j.cclet.2021.02.026 shu

Allylation and alkylation of oxindoleketimines via imine umpolung strategy

Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmacy, Changzhou University, Changzhou 213164, China

shenmh@cczu.edu.cn

markxu@cczu.edu.cn

Received Date: 1 December 2020
Revised Date: 3 February 2021
Accepted Date: 10 February 2021
Available Online: 16 February 2021

Figures(6)

When treated with an alkoxide base like t-BuOK in aprotic solvent, N-diphenylmethyl imino oxindoles, made conveniently through condensation of corresponding isatins with N-diphenylmethyl amine, are deprotonated to form azaallyl anions. Allylation and alkylation of this type of intermediates proceed smoothly with diverse C-electrophiles. Acidic work up finishes 3-amino-3-allyl/alkyl oxindoles. The overall transformation equals to an umpolung process at the C3 of isatins.
- Allylation,
- Alkylation,
- Azaallylaion,
- Umpolung,
- Oxindleketamine,
- Spiro oxindole
1. [1]
  J. Kaur, B.P. Kaur, S.S. Chimni, Org. Biomol. Chem. 18 (2020) 4692-4708. doi: 10.1039/d0ob00777c
2. [2]
  J. Kaur, S.S. Chimni, S. Mahajan, et al., RSC Adv. 5 (2015) 52481-52496. doi: 10.1039/C5RA06969F
3. [3]
  M. Rottmann, C. McNamara, B.K.S. Yeung, et al., Science 329 (2010) 1175-1180. doi: 10.1126/science.1193225
4. [4]
  S. Crosignani, C. Jorand-Lebrun, P. Page, et al., ACS Med. Chem. Lett. 2 (2011) 644-649. doi: 10.1021/ml2001196
5. [5]
  S.U. Maheswari, K. Balamurugan, S. Perumal, et al., Bioorg. Med. Chem. Lett. 20 (2010) 7278-7282. doi: 10.1016/j.bmcl.2010.10.080
6. [6]
  P. Prasanna, K. Balamurugan, S. Perumal, et al., Eur. J. Med. Chem. 45 (2010) 5653-5661. doi: 10.1016/j.ejmech.2010.09.019
7. [7]
  R.R. Kumar, S. Perumal, P. Senthilkumar, et al., J. Med. Chem. 51 (2008) 5731-5735. doi: 10.1021/jm800545k
8. [8]
  U. Anthoni, L. Chevolot, C. Larsen, et al., J. Org. Chem. 52 (1987) 4709-4712. doi: 10.1021/jo00230a010
9. [9]
  M. Ochi, K. Kawasaki, H. Kataoka, et al., Biochem. Biophys. Res. Commun. 283 (2001) 1118-1123. doi: 10.1006/bbrc.2001.4911
10. [10]
  R.S. Kumar, S.M. Rajesh, S. Perumal, et al., Eur. J. Med. Chem. 45 (2010) 411-422. doi: 10.1016/j.ejmech.2009.09.044
11. [11]
  L. Chen, J. Zhang, Z. Zhang, et al., WO2008034736A2, 2008.
12. [12]
  A.K. Ghosh, G. Schiltz, R.S. Perali, et al., Bioorg. Med. Chem. Lett. 16 (2006) 1869-1873. doi: 10.1016/j.bmcl.2006.01.011
13. [13]
  K. Ohmatsu, Y. Ando, T. Nakashima, et al., Chem 1 (2016) 802-810. doi: 10.1016/j.chempr.2016.10.012
14. [14]
  J. Chen, B.Q. Huang, Z.Q. Wang, et al., Org. Lett. 21 (2019) 9742-9746. doi: 10.1021/acs.orglett.9b03911
15. [15]
  S. Chen, G.L. Wang, S. -W. Xu, et al., Org. Biomol. Chem. 17 (2019) 6551-6556. doi: 10.1039/c9ob01203f
16. [16]
  W.T. Fan, N.K. Li, L. Xu, et al., Org. Lett. 19 (2017) 6626-6629. doi: 10.1021/acs.orglett.7b03341
17. [17]
  H.Z. Gui, Y. Wei, M. Shi, Org. Biomol. Chem. 16 (2018) 9218-9222. doi: 10.1039/c8ob02748j
18. [18]
  H.Z. Gui, X.Y. Wu, Y. Wei, et al., Adv. Synth. Catal. 361 (2019) 5466-5471. doi: 10.1002/adsc.201901124
19. [19]
  K.Q. Hou, F. Zhou, X.P. Chen, et al., J. Org. Chem. 85 (2020) 9661-9671. doi: 10.1021/acs.joc.0c00981
20. [20]
  C.W. Lei, C.B. Zhang, Z.H. Wang, et al., Org. Chem. Front. 7 (2020) 499-506. doi: 10.1039/c9qo01039d
21. [21]
  N.K. Li, W.T. Fan, J.Q. Zhang, et al., Chem. Commun. (Camb. ) 54 (2018) 2260-2263. doi: 10.1039/C7CC09489B
22. [22]
  N. Lin, X.W. Long, Q. Chen, et al., Tetrahedron 74 (2018) 3734-3741. doi: 10.1016/j.tet.2018.05.052
23. [23]
  Y. Lin, B.L. Zhao, D. -M. Du, J. Org. Chem. 83 (2018) 7741-7750. doi: 10.1021/acs.joc.8b00632
24. [24]
  X.J. Song, H.X. Ren, M. Xiang, et al., J. Org. Chem. 85 (2020) 9290-9300. doi: 10.1021/acs.joc.9b03337
25. [25]
  Y.H. Wang, J.S. Tian, P.W. Tan, et al., Angew. Chem. Int. Ed. 59 (2020) 1634-1643. doi: 10.1002/anie.201910864
26. [26]
  X.C. Yang, M.M. Liu, F. Mathey, et al., J. Org. Chem. 84 (2019) 7762-7775. doi: 10.1021/acs.joc.9b00645
27. [27]
  Z.H. You, Y.H. Chen, Y. Tang, et al., Org. Lett. 20 (2018) 6682-6686. doi: 10.1021/acs.orglett.8b02731
28. [28]
  B.L. Zhao, D.M. Du, Adv. Synth. Catal. 361 (2019) 3412-3419. doi: 10.1002/adsc.201900218
29. [29]
  J.Q. Zhao, X.J. Zhou, Y.Z. Chen, et al., Adv. Synth. Catal. 360 (2018) 2482-2487. doi: 10.1002/adsc.201800266
30. [30]
  J.Q. Zhao, X.J. Zhou, Y. Zhou, et al., Org. Lett. 20 (2018) 909-912. doi: 10.1021/acs.orglett.7b03667
31. [31]
  Y. Zhu, J. Guo, S. Jin, et al., Org. Biomol. Chem. 16 (2018) 1751-1759. doi: 10.1039/C8OB00306H
32. [32]
  X. Zuo, S. Chen, S.W. Xu, et al., Synthesis 51 (2019) 2339-2350. doi: 10.1055/s-0037-1610875
33. [33]
  T. Arai, K. Araseki, J. Kakino, Org. Lett. 21 (2019) 8572-8576. doi: 10.1021/acs.orglett.9b03148
34. [34]
  Y. Fan, J. Lu, F. Sha, et al., J. Org. Chem. 84 (2019) 11639-11648. doi: 10.1021/acs.joc.9b01566
35. [35]
  S. Hajra, S. Laskar, B. Jana, Chem. Eur. J. 25 (2019) 14688-14693. doi: 10.1002/chem.201903512
36. [36]
  T. Kang, W. Cao, L. Hou, et al., Angew. Chem. Int. Ed. 58 (2019) 2464-2468. doi: 10.1002/anie.201810961
37. [37]
  J. Wang, Y. Liu, Y. Liu, et al., Tetrahedron 75 (2019) 2883-2892. doi: 10.1016/j.tet.2019.04.015
38. [38]
  J. Wang, Q. Zhang, B. Zhou, et al., iScience 16 (2019) 511-523. doi: 10.1016/j.isci.2019.06.006
39. [39]
  G. Wu, H. Xu, Z. Liu, et al., Org. Lett. 21 (2019) 7708-7712. doi: 10.1021/acs.orglett.9b02440
40. [40]
  Y.N. Yu, W.Y. Qi, C.Y. Wu, et al., Org. Lett. 21 (2019) 7493-7497. doi: 10.1021/acs.orglett.9b02787
41. [41]
  J. Zhou, G.D. Zhu, L. Wang, et al., Org. Lett. 21 (2019) 8662-8666. doi: 10.1021/acs.orglett.9b03276
42. [42]
  J. Zhu, S. Fang, S. Jin, et al., Org. Biomol. Chem. 17 (2019) 8745-8748. doi: 10.1039/c9ob01347d
43. [43]
  L. Cai, X. Liu, J. Wang, et al., Chem. Commun. (Camb. ) 56 (2020) 10361-10364. doi: 10.1039/d0cc04966b
44. [44]
  V. Filatov, M. Kukushkin, J. Kuznetsova, et al., RSC Adv. 10 (2020) 14122-14133. doi: 10.1039/d0ra02374d
45. [45]
  Z. Li, J. Peng, C. He, et al., J. Org. Chem. 85 (2020) 3894-3901. doi: 10.1021/acs.joc.9b03000
46. [46]
  C. Liu, F.X. Tan, J. Zhou, et al., Org. Lett. 22 (2020) 2173-2177. doi: 10.1021/acs.orglett.0c00262
47. [47]
  S. Nakamura, K. Matsuzaka, T. Hatanaka, et al., Org. Lett. 22 (2020) 2868-2872. doi: 10.1021/acs.orglett.0c00289
48. [48]
  G.Y. Ran, C. Chen, X.X. Yang, et al., Org. Lett. 22 (2020) 4732-4736. doi: 10.1021/acs.orglett.0c01534
49. [49]
  V.U.B. Rao, S. Singh, K.N. Tripathi, et al., Synthesis 52 (2020) 2551-2562. doi: 10.1055/s-0040-1707907
50. [50]
  M. Rodriguez-Rodriguez, A. Maestro, J.M. Andres, et al., Adv. Synth. Catal. 362 (2020) 2744-2754. doi: 10.1002/adsc.202000238
51. [51]
  R. Yonesaki, I. Kusagawa, H. Morimoto, et al., Chem. Asian J. 15 (2020) 499-502. doi: 10.1002/asia.201901745
52. [52]
  H. Zhang, Y. Luo, C. Zhu, et al., Org. Lett. 22 (2020) 5217-5222. doi: 10.1021/acs.orglett.0c01857
53. [53]
  Y. Zhao, L. Cai, T. Huang, et al., Adv. Synth. Catal. 362 (2020) 1309-1316. doi: 10.1002/adsc.201901380
54. [54]
  W.R. Zhu, K. Liu, J. Weng, et al., Org. Lett. 22 (2020) 5014-5019. doi: 10.1021/acs.orglett.0c01578
55. [55]
  Y. Wu, L. Hu, Z. Li, et al., Nature 523 (2015) 445-450. doi: 10.1038/nature14617
56. [56]
  Y. Wang, L.F. Deng, X. Zhang, et al., Org. Lett. 21 (2019) 6951-6956. doi: 10.1021/acs.orglett.9b02550
57. [57]
  L.M. Shi, X.S. Sun, C. Shen, et al., Org. Lett. 21 (2019) 4842-4848. doi: 10.1021/acs.orglett.9b01738
58. [58]
  J. Liu, C.G. Cao, H.B. Sun, et al., J. Am. Chem. Soc. 138 (2016) 13103-13106. doi: 10.1021/jacs.6b05288
59. [59]
  C.X. Zhuo, A. Fürstner, J. Am. Chem. Soc. 140 (2018) 10514-10523. doi: 10.1021/jacs.8b05094
60. [60]
  X. Li, J. Su, Z. Liu, et al., Org. Lett. 18 (2016) 956-959. doi: 10.1021/acs.orglett.5b03566
61. [61]
  W.W. Chen, B. Zhao, Synlett 31 (2020) 1543-1550. doi: 10.1055/s-0040-1707157
62. [62]
  S. Tang, X. Zhang, J. Sun, et al., Chem. Rev. 118 (2018) 10393-10457. doi: 10.1021/acs.chemrev.8b00349
63. [63]
  X.S. Sun, X.H. Wang, H.Y. Tao, et al., Chem. Sci. 11 (2020) 10984-10990. doi: 10.1039/d0sc04685j
64. [64]
  K. Li, A.E. Weber, L. Tseng, et al., Org. Lett. 19 (2017) 4239-4242. doi: 10.1021/acs.orglett.7b01886
65. [65]
  L.R. Reddy, S. Kotturi, R. Shenoy, et al., Org. Lett. 20 (2018) 5423-5426. doi: 10.1021/acs.orglett.8b02331
66. [66]
  S. Wang, X. Qian, Y. Chang, et al., J. Org. Chem. 83 (2018) 4054-4069. doi: 10.1021/acs.joc.8b00491
67. [67]
  M. Zhan, X. Pu, B. He, et al., Org. Lett. 20 (2018) 5857-5860. doi: 10.1021/acs.orglett.8b02536
68. [68]
  P.E. Daniel, A.E. Weber, S.J. Malcolmson, Org. Lett. 19 (2017) 3490-3493. doi: 10.1021/acs.orglett.7b01471
69. [69]
  P. Chen, Z. Yue, J. Zhang, et al., Angew. Chem. Int. Ed. 55 (2016) 13316-13320. doi: 10.1002/anie.201607918
70. [70]
  S. Peng, Y.X. Song, J.Y. He, et al., Chin. Chem. Lett. 30 (2019) 2287-2290.
71. [71]
  Z. Cao, Q. Zhu, Y.W. Lin, et al., Chin. Chem. Lett. 30 (2019) 2132-2138.
72. [72]
  D.F. Li, H.S. Jin, J.R. Zhang, et al., Eur. J. Org. Chem. 2018 (2018) 4787-4794. doi: 10.1002/ejoc.201800881
73. [73]
  D. Ma, Q. Cai, Org. Lett. 5 (2003) 3799-3802.
74. [74]
  D. Ma, Y. Zhang, J. Yao, et al., J. Am. Chem. Soc. 120 (1998) 12459-12467.
75. [75]
  S.S. Panda, R.A. Jones, P. Bachawala, et al., Mini-Rev. Med. Chem. 17 (2017) 1515-1536.
76. [76]
  Y.T. Yang, J.F. Zhu, G. Liao, et al., Curr. Med. Chem. 25 (2018) 2233-2244. doi: 10.2174/0929867325666171129131311
77. [77]
  L.M. Zhou, R.Y. Qu, G.F. Yang, Expert Opin. Drug Discovery 15 (2020) 603-625. doi: 10.1080/17460441.2020.1733526
1. [1]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
2. [2]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
3. [3]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
4. [4]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
5. [5]
  Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
6. [6]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
7. [7]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
8. [8]
  Jindan Zhang , Zhenghong Li , Chi Li , Mengqi Zhu , Shicheng Tang , Kaicong Cai , Zhibin Cheng , Chulong Liu , Shengchang Xiang , Zhangjing Zhang . Revealing a new doping mechanism of spiro-OMeTAD with tBP participation through the introduction of radicals into HTM. Chinese Chemical Letters, 2025, 36(3): 110046-. doi: 10.1016/j.cclet.2024.110046
9. [9]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1221)
HTML views(270)

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