ARTICLES

Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light

  • Limei Xu ,
  • Linyan Lu ,
  • Jinzhong Cai ,
  • Yadong Feng ,
  • Xiuling Cui
Expand
  • a College of Environment and Public Health, Xiamen Huaxia University, Xiamen, Fujian 361024
    b Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen, Fujian 361021

Received date: 2021-10-15

  Revised date: 2021-11-17

  Online published: 2021-12-02

Supported by

Fujian Education and Scientific Research Project for Young and Middle-Aged Teachers(JAT190990)

Abstract

A metal-free radical coupling reaction of aminophenols with amines under UV-light has been successfully developed to synthesize diaminobenzoquinone imines in high yields, in which the commercially available and cheap t-butyl hydroperoxide (TBHP) was used as an oxidant. This protocol provides an easy and green approach for the construction of benzoquinone imines with potential pharmaceutical interest avoiding metal catalyst or photocatalyst.

Cite this article

Limei Xu , Linyan Lu , Jinzhong Cai , Yadong Feng , Xiuling Cui . Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1210 -1215 . DOI: 10.6023/cjoc202110022

References

[1]
(a) Fabre, B. Chem. Rev. 2016, 116, 4808.
[1]
(b) Cavalli, A.; Bolognesi, M. L.; Capsoni, S.; Andrisano, V.; Bartolini, M.; Margotti, E.; Cattaneo, A.; Recanatini, M.; Melchiorre, C. Angew. Chem., Int. Ed. 2007, 46, 3689.
[1]
(c) Nachtsheim, B. J. Nat. Chem. 2020, 12, 326
[1]
(d) Liu, S.; Shen, T.; Luo, Z.; Liu, Z. Chem. Commun. 2019, 55, 402.
[2]
(a) Yu, J.; Zhang, H.; Lu, Q.; Ding, X.; Liu, S.; Li, Y. Chem. Ind. Eng. Prog. 2015, 34, 1115.
[2]
(b) Halhalli, M. R.; Sellergren, B. Polym. Chem. 2015, 6, 7320.
[3]
Rajappa, S.; Sreenivasan, R.; Rane, A. V. Tetrahedron Lett. 1983, 24, 3155.
[4]
Nair, V.; Rajesh, C.; Dhanya, R.; Vinod, A. U. Tetrahedron Lett. 2001, 42, 2045.
[5]
Nair, V.; Dhanya, R.; Viji, S. Tetrahedron 2005, 61, 5843.
[6]
Parker, K. A.; Mindt, T. L. Org. Lett. 2016, 4, 4265.
[7]
(a) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
[7]
(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[7]
(c) Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97.
[7]
(d) Tobisu, M.; Furukawa, T.; Chatani, N. Chem. Lett. 2013, 42, 1203.
[7]
(e) Gomes, F.; Narbonne, V.; Blanchard, F.; Maestri, G.; Malacria, M. Org. Chem. Front. 2015, 2, 464.
[7]
(f) Wu, Y.; Pi, C.; Cui, X.; Wu, Y. Org. Lett. 2020, 22, 361.
[7]
(g) Ren, J.; Yan, X.; Cui, X.; Pi, C.; Wu, Y.; Cui, X. Green Chem. 2020, 22, 265.
[7]
(h) Huang, Y.; Pi, C.; Tang, Z.; Wu, Y.; Cui, X. Chin. Chem. Lett. 2020, 31,3237.
[7]
(i) Yao, Z.; Lin, X.; Chauvin, R.; Wang, L.; Gras, E.; Cui, X. Chin. Chem. Lett. 2020, 31, 3250.
[7]
(j) Wang, Y.; Gao, X.; Ji, J.; Cui, X.; Pi, C.; Zhao, L.; Wu, Y. Chin. Chem. Lett. 2021, 32, 1696.
[7]
(k) Li, H.; Han, Y.; Yang, Z.; Yao, Z.; Wang, L.; Cui, X. Chin. Chem. Lett. 2021, 32, 1709.
[7]
(l) Ren, J.; Huang, Y.; Pi, C.; Cui, X.; Wu, Y. Chin. Chem. Lett. 2021, 32, 2592.
[7]
(m) Chen, Z.; Zhang, H.; Zhou, S.; Cui, X. Chin. J. Org. Chem. 2020, 40, 3866. (in Chinese)
[7]
( 陈志超, 张红, 周树峰, 崔秀灵, 有机化学, 2020, 40, 3866.)
[7]
(n) Xiao, Y.; Yang, Y.; Zhang, F.; Feng, Y.; Cui, X. Chin. J. Org. Chem. 2021, 41, 4808. (in Chinese)
[7]
( 肖玉娟, 杨阳, 张凡, 冯亚栋, 崔秀灵, 有机化学, 2021, 41, 4808.)
[7]
(o) Wu, Y.; Chen, J.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W. Green Chem. 2021, 23, 3950.
[7]
(p) Yi, R.; He, W. Chin. J. Org. Chem. 2021, 41, 1267. (in Chinese)
[7]
易荣楠, 何卫民, 有机化学, 2021, 41, 1267).
[8]
Kwon, K.; Simons, R. T.; Nandakumar, M.; Roizen, J. L. Chem. Rev. 2022, 122, 2353.
[9]
Vitale, A.; Bongiovanni, R.; Ameduri, B. Chem. Rev. 2015, 115, 8835.
[10]
Feng, Y.; Liu, Y.; Fu, Q.; Zou, Z.; Shen, J.; Cui, X. Chin. Chem. Lett. 2020, 31, 733.
[11]
(a) Liang, D.; Tan, L.; Xiao, W.; Chen, J. Chem. Commun. 2020, 56, 3777.
[11]
(b) Xie, L.; Fang, T.; Tan, J.; Zhang, B.; Cao, Z.; Yang, L.; He, W. Green Chem. 2019, 21, 3858.
[11]
(c) Zhu, S.; Zhou, J.; Wu, Q.; Hao, W.; Tu, S.; Jiang, B. Org. Chem. Front. 2020, 7, 2975.
[11]
(d) Feng, Y.; Wu, Z.; Chen, T.; Fu, Q.; You, Q, Shen, J.; Cui, X. Chin. Chem. Lett. 2020, 31, 3263.
[11]
(e) Yu, X.; Chen, J.; Chen, H.; Xiao, W.; Chen, J. Org. Lett. 2020, 22. 2333.
[11]
(f) Zhao, Q.; Zhou, X.; Xu, S.; Wu, Y.; Xiao, W.; Chen, J. Org. Lett. 2020, 22, 2470.
[11]
(g) Shen, Z.; Pi, C.; Cui, X.; Wu, Y. Chin. Chem. Lett. 2019, 30, 1374.
[11]
(h) Gao, Q.; Hao, W.; Liu, F.; Tu, S.; Wang, S.; Li, G.; Jiang, B. Chem. Commun. 2016, 52, 900.
[11]
(i) Zhou, P.; Wang, J.; Zhang, T. Chem. Commun. 2018, 54, 164.
[11]
(j) Yu, H.; Pi, C.; Wang, Y.; Cui, X.; Wu, Y. Chin. J. Org. Chem. 2018, 38, 124. (in Chinese)
[11]
( 余海洋, 皮超, 王勇, 崔秀灵, 吴养洁, 有机化学, 2018, 38, 124.)
[11]
(k) Shi, Z.-J.; Wang, L.-H.; Cui, X. Chin. J. Org. Chem. 2019, 39, 1596. (in Chinese)
[11]
( 施兆江, 王连会, 崔秀灵, 有机化学, 2019, 39, 1596.)
[11]
(l) Liu, R.; Yang, M.; Qiu, G.; Zhang, L.; Wang, Y.; Luo, J. Chin. J. Org. Chem. 2020, 40, 2071. (in Chinese)
[11]
( 刘仁志, 杨民, 邱观音生, 张莲鹏, 王玉超, 罗劲, 有机化学, 2020, 40, 2071.)
[11]
(m) Peng, S.; Lin, Y.; He, W. Chin. J. Org. Chem. 2020, 40, 541. (in Chinese)
[11]
( 彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.)
[11]
(n) Yuan, X.; Yang, G.; Yu, B. Chin. J. Org. Chem. 2020, 40, 3620. (in Chinese)
[11]
( 袁晓亚, 杨国平, 於兵, 有机化学, 2020, 40, 3620.)
Outlines

/