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.
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