Citation: Feng Yadong, Liu Ying, Fu Qi, Zou Zhongai, Shen Jinhai, Cui Xiuling. Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines[J]. Chinese Chemical Letters, ;2020, 31(3): 733-735. doi: 10.1016/j.cclet.2019.09.026 shu

Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines

Feng Yadong ^a,b,*, ,
Liu Ying ^a ,
Fu Qi ^a ,
Zou Zhongai ^a ,
Shen Jinhai ^a ,
Cui Xiuling ^b,*,

a.
College of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, China
b.
Engineering Research Center of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China

fengyd@hxxy.edu.cn

cuixl@hqu.edu.cn

Received Date: 24 July 2019
Revised Date: 9 September 2019
Accepted Date: 12 September 2019
Available Online: 12 September 2019

Figures(3)

A ferrocene-initiated radical reaction of benzoquinone with amines has been successfully developed for the direct access to diaminobenzoquinone imines in high yields, in which the commercially available and cheap ferrocene was employed as a radical initiator and TBHP was used as an oxidant. Moreover, this reaction could be achieved with low loading of ferrocene (0.5 mol%). This protocol is highly efficient with good substrate tolerance and provides a new approach for the construction of benzoquinone imines with potential pharmaceutical interest.
- Benzoquinone imines,
- Ferrocene-initiated,
- Radical process,
- Benzoquinone,
- Amines
1. [1]
  (a) E. Prochazka, B.I. Escher, M.J. Plewa, F.D.L. Leusch, Chem. Res. Toxicol. 28 (2015) 2059-2068;
  (b) R. Mout, Z.D. Xu, A.K.H. Wolf, V.J. Davisson, G.K. Jarori, Malar. J.11 (2012) 54-54;
  (c) D. Tasdemir, R. Brun, V. Yardley, S.G. Franzblau, P. Ruedi, Chem. Biodiv. 3 (2006) 1230-1237;
  (d) L.F. Fieser, E.M. Chamberlin, J. Am. Chem. Soc. 70 (1948) 71-75;
  (e) B. Joy, S.N. Kumar, M.S. Soumya, et al., Phytomedicine 21 (2014) 1292-1297;
  (f)A.Cavalli, M.L.Bolognesi, S.Capsoni, etal., Angew.Chem.Int.Ed.46 (2007)3689-3692;
  (g) T.J. Monks, P. Hanzlik, G.M. Cohen, D. Ross, D.G. Graham, Toxicol. Appl. Pharmacol. 112 (1992) 2-16.
2. [2]
  (a) J. Yu, H. Zhang, Q. Lu, et al., Chem. Ind. Eng. Progress 34 (2015) 1115-1121;
  (b) M.R. Halhalli, B. Sellergren, Polym. Chem. 6 (2015) 7320-7332;
  (c) M.A. Hanna, M.M. Girges, Acta Polym. 41 (1990) 354-360;
  (d) S. Rajappa, S.J. Shenoy, Tetrahedron 42 (1986) 5739-5746.
3. [3]
  S. Rajappa, R. Sreenivasan, A.V. Rane, Tetrahedron Lett. 24 (1983) 3155-3158. doi: 10.1016/S0040-4039(00)88121-6
4. [4]
  V. Nair, C. Rajesh, R. Dhanya, A.U. Vinod, Tetrahedron Lett. 42 (2001) 2045-2046. doi: 10.1016/S0040-4039(01)00072-7
5. [5]
  V. Nair, R. Dhanya, S. Viji, Tetrahedron 61 (2005) 5843-5848. doi: 10.1016/j.tet.2005.04.008
6. [6]
  K.A. Parker, T.L. Mindt, Org. Lett. 4 (2002) 4265-4268. doi: 10.1021/ol026849x
7. [7]
  (a) Y. Park, Y. Kim, S. Chang, Chem. Rev. 117 (2017) 9247-9301;
  (b) J. Kim, S. Chang, Angew. Chem. Int. Ed. 53 (2014) 2203-2207;
  (c) T. Kang, Y. Kim, D. Lee, Z. Wang, S. Chang, J. Am. Chem. Soc.136 (2014) 4141-4144;
  (d) H. Hwang, J. Kim, J. Jeong, S. Chang, J. Am. Chem. Soc. 136 (2014) 10770-10776;
  (e) C. Pi, X. Cui, Y. Wu, J. Org. Chem. 80 (2015) 7333-7339;
  (f) M.E. Wei, L.H. Wang, Y.Y. Li, X. Cui, Chin. Chem. Lett. 26 (2015) 1336-1340;
  (g) X. Han, P. Lin, Q. Li, Chin. Chem. Lett. 30 (2019) 1495-1502;
  (h) S. Yuan, S. Wang, M. Zhao, et al., Chin. Chem. Lett. 31 (2020) 349-352;
  (i) Q. Huang, L. Zhu, D. Yi, X. Zhao, W. Wei, Chin. Chem. Lett. 31 (2020) 373-376;
  (j) X. Zhang, S. Dong, Q. Ding, X. Fan, G. Zhang, Chin.Chem. Lett. 30 (2019) 375-378;
  (k) L. Xie, S. Peng, L. Jiang, et al., Org. Chem. Front. 6 (2019) 167-171;
  (l) L. Xie, S. Peng, F. Liu, et al., ACS Sustainable Chem. Eng. 7 (2019) 7193-7199.
8. [8]
  J.A. Jordan-Hore, C.C.C. Johansson, M. Gulias, E.M. Beck, M.J. Gaunt, J. Am. Chem. Soc. 130 (2008) 16184-16186. doi: 10.1021/ja806543s
9. [9]
  S.M. Paradine, M.C. White, J. Am. Chem. Soc. 134 (2012) 2036-2039. doi: 10.1021/ja211600g
10. [10]
  (a) Y. Feng, Y. Li, Y. Yu, L. Wang, X. Cui, RSC Adv. 8 (2018) 8450-8454;
  (b) Y. Feng, Z. Zhang, Q. Fu, et al., Chin. Chem. Lett. 31 (2020) 58-60.
11. [11]
  (a) C. Liu, D. Liu, A. Lei, Acc. Chem. Res. 47 (2014) 3459-3470;
  (b) S.A. Girard, T. Knauber, C.J. Li, Angew. Chem. Int. Ed. 53 (2014) 74-100;
  (c) R. Braslau, M.O. Anderson, F. Rivera, et al., Tetrahedron 58 (2002) 5513-5523;
  (d) S. Bath, N.M. Laso, H. Lopez-Ruiz, B. Quiclet-Sire, S.Z. Zard, Chem. Commun. 34 (2003) 204-205;
  (e) J. Wang, C. Liu, J. Yuan, A. Lei, Angew. Chem. Int. Ed. 52 (2013) 2256-2259;
  (f) J. Xie, J. Yu, M. Rudolph, F. Rominger, A.S. Hashmi, Angew. Chem. Int. Ed. 55 (2016) 9416-9421;
  (g) C. Wang, J. Qin, X. Shen, et al., Angew. Chem. Int. Ed. 55 (2016) 685-688;
  (h) L.Y. Xie, S. Peng, F. Liu, et al., Org. Chem. Front. 5 (2018) 2604-2609;
  (i) L.Y. Xie, S. Peng, F. Liu, et al., Adv. Synth. Catal. 360 (2018) 4259-4264;
  (j) L. Xie, T. Fang, J. Tan, et al., Green Chem. 21 (2019) 3858-3863.
12. [12]
  (a) D. Leifert, C.G. Daniliuc, A. Studer, Org. Lett. 15 (2013) 6286-6289;
  (b) S. Wertz, D. Leifert, A. Studer, Org. Lett. 15 (2013) 928-931.
13. [13]
  Y. Feng, H. Zhang, Y. Yu, L. Yang, X. Cui, Eur. J. Org. Chem. 16 (2019) 2740-2744.
14. [14]
  (a) L. Wang, D. Xiong, L. Jie, C. Yu, X. Cui, Chin. Chem. Lett. 29 (2018) 907-910;
  (b) L. Xu, T. Li, L. Wang, X. Cui, J. Org. Chem. 84 (2019) 560-567;
  (c) Z. Yang, L. Jie, Z. Yao, et al., Adv. Catal. Synth. 1 (2019) 214-258;
  (d) P. Chao, X. Yin, X. Cui, Y. Ma, Y. Wu, Org. Lett. 7 (2019) 2081-2084;
  (e) J. Ren, C. Pi, Y. Wu, X. Cui, Org. Lett. 11 (2019) 4067-4071; f) S. Huang, H. Li, X. Sun, et al., Org. Lett. 21 (2019) 5570-5574;
  (g) B. Wu, Z. Yang, H. Zhang, L. Wang, Cui X, Chem. Commun. 55 (2019) 4190-4193;
  (h) Z. Yang, Z. Song, L. Jie, L. Wang, X. Cui, Chem. Commun. 55 (2019) 6094-6097;
  (i) T. Yuan, C. Pi, C. You, et al., Chem. Commun. 55 (2019) 163-166;
  (k) T. Wan, S. Du, C. Pi, Y. Wang, R. Li, Y. Wu, X. Cui, ChemCatChem 11 (2019) 3791-3796;
  (l) S. Du, C. Pi, T. Wan, Y. Wu, X. Cui, Adv. Synth. Catal. 361 (2019) 1766-1770;
  (m) Z.H. Shen, C. Pi, X. Cui, Y. Wu, Chin. Chem. Lett. 30 (2019) 1374-1378.
1. [1]
  Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
2. [2]
  Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp²)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901
3. [3]
  Jian Peng , Yue Jiang , Shuangyu Wu , Yanran Cheng , Jingyu Liang , Yixin Wang , Zhuo Li , Sijie Lin . A nonradical oxidation process initiated by Ti-peroxo complex showed high specificity toward the degradation of tetracycline antibiotics. Chinese Chemical Letters, 2024, 35(5): 108903-. doi: 10.1016/j.cclet.2023.108903
4. [4]
  Baihui Zheng , Dandan Zhang , Baoping Ren , Yifei Li , Qun Liu , Ling Pan . Divergent site-selective synthesis of deuterated pyrroles from radical initiated cyclizations of N-propargyl enamines. Chinese Chemical Letters, 2026, 37(5): 111544-. doi: 10.1016/j.cclet.2025.111544
5. [5]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
6. [6]
  Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
7. [7]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
8. [8]
  Xin-Han Wang , Ying Huang , Chun-Lin Zhang , Song Ye . γ-C(sp³)-H acylation of aliphatic amines enabled by cooperative photoredox NHC/Pd catalysis. Chinese Chemical Letters, 2026, 37(5): 111484-. doi: 10.1016/j.cclet.2025.111484
9. [9]
  Xiuhua Wang , Jianrong Steve Zhou . A dicationic nickel complex-catalyzed asymmetric synthesis of chiral benzylic amines: Evolution from reductive amination to borrowing hydrogen reaction. Chinese Chemical Letters, 2026, 37(2): 111148-. doi: 10.1016/j.cclet.2025.111148
10. [10]
  Dongke Zhang , Li-Ao Ding , Qiuyu Xiang , Zhuojun Li , Qian Wu . P^Ⅲ/P^Ⅴ-catalytic platform enabling N-fluoro-thiocarbonylation of diaryl amines for modular synthesis of tertiary N-trifluoromethylamines. Chinese Chemical Letters, 2026, 37(5): 111461-. doi: 10.1016/j.cclet.2025.111461
11. [11]
  Xiaoya Zhuo , Xiangwen Tan , Yi Wang , Wanqing Wu , Huanfeng Jiang . Palladium catalyzed tandem Heck/Tsuji-Trost and 6-endo cyclization reactions of aryl iodides, vinylacetic acid, and aryl amines. Chinese Chemical Letters, 2026, 37(6): 111777-. doi: 10.1016/j.cclet.2025.111777
12. [12]
  Yuan Zhang , Shenghao Gong , A.R. Mahammed Shaheer , Rong Cao , Tianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH₂-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587
13. [13]
  Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446
14. [14]
  Jun Liu , Zhaoyu Feng , Renming Pan , Xiaolong Yu , Meijuan Zhou , Gang Zhao , Hongyu Wang . Enantioselective regulation to coronal polyheterocyclic compounds via phosphonium salt-catalyzed cycloadditions of azomethine imines with γ-butenolides. Chinese Chemical Letters, 2025, 36(8): 110647-. doi: 10.1016/j.cclet.2024.110647
15. [15]
  Nianhua Luo , Jiayi Jiang , Muhammad Suleman , Zhaowen Liu , Shuping Huang , Wei Xiao , Jie Wu , Jiapian Huang . Advances in radical Smiles rearrangement. Chinese Chemical Letters, 2026, 37(2): 111556-. doi: 10.1016/j.cclet.2025.111556
16. [16]
  Haitao Liu , Youlin Deng , Dan Ling , Lingzhu Chen , Zhichao Jin . Asymmetric catalysis for the synthesis of planar chiral ferrocene derivatives. Chinese Chemical Letters, 2026, 37(3): 111793-. doi: 10.1016/j.cclet.2025.111793
17. [17]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
18. [18]
  Ziwang Liu , Xiaoqian Wang , Honglin Qin , Yan Chen , Ling Xia , Xuanjing Wang , Yanhua Lai , Gongke Li . Research progress of the Maillard reaction process monitoring. Chinese Chemical Letters, 2026, 37(4): 111742-. doi: 10.1016/j.cclet.2025.111742
19. [19]
  Zhen Zhang , Rui Su , Xiongjun Xiao , Jiaxin Yang , Yuwei Li , Tiemin Sun , Yang Liu , Chengjun Wu . A continuous-flow process for the synthesis of balsalazide disodium. Chinese Chemical Letters, 2026, 37(7): 111965-. doi: 10.1016/j.cclet.2025.111965
20. [20]
  Qiang Fang , Yingbo Lu , Jianying Huang , Cheng Zhang , Jing Wu , Shijun Li . An electrochemical immunosensor based on an antibody-ferrocene-functionalized covalent organic framework. Chinese Chemical Letters, 2026, 37(2): 111218-. doi: 10.1016/j.cclet.2025.111218

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(2193)
HTML views(101)

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