Citation: Jin-Yang Chen, Chun-Tao Zhong, Qing-Wen Gui, Yuan-Ming Zhou, Yang-Yang Fang, Kai-Jian Liu, Ying-Wu Lin, Zhong Cao, Wei-Min He. Practical and sustainable approach for clean preparation of 5-organylselanyl uracils[J]. Chinese Chemical Letters, ;2021, 32(1): 475-479. doi: 10.1016/j.cclet.2020.09.034 shu

Practical and sustainable approach for clean preparation of 5-organylselanyl uracils

a.
College of Chemistry and Chemical Engineering, Yangtze Normal University, Chongqing 408000, China
b.
Department of Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, China
c.
Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, China
d.
School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China

weiminhe2016@yeah.net

Received Date: 5 August 2020
Revised Date: 3 September 2020
Accepted Date: 21 September 2020
Available Online: 23 September 2020

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An eco-friendly, sustainable and practical method for the efficient preparation of 5-organylselanyl uracils through the electrochemical selenylation of uracils and diorganyl diselenides at room temperature under oxidant- and external electrolyte-free conditions was developed.
- Selenylation,
- Electrochemistry,
- Diorganyl diselenides,
- Atom-economy,
- Recyclability
1. [1]
  (a) Y. Kim, C.J. Li, Green Synth. Catal. 1 (2020) 1-11;
  (b) Z. Cao, Q. Zhu, Y.W. Lin, W.M. He, Chin. Chem. Lett. 30 (2019) 2132-2138;
  (c) K.J. Liu, T.Y. Zeng, J.L. Zeng, et al., Chin. Chem. Lett. 30 (2019) 2304-2308;
  (d) J. Shi, W. Wei, Chin. J. Org. Chem. 40 (2020) 2170-2172;
  (e) L.Y. Xie, Y.S. Liu, H.R. Ding, et al., Chin. J. Catal. 41 (2020) 1168-1173;
  (f) J.Y. Liao, Q.Y. Wu, X. Lu, et al., Green Chem. 21 (2019) 6567-6573.
2. [2]
  (a) A. Pałasz, D. Ciez, Eur. J. Med. Chem. 97 (2015) 582-611;
  (b) D.P. Angelika, D. Joanna, P. Marlena, et al., Anticancer Agents Med. Chem. 20 (2020) 359-368.
3. [3]
  (a) B. Banerjee, M. Koketsu, Coord. Chem. Rev. 339 (2017) 104-127;
  (b) Q.B. Zhang, Y.L. Ban, P.F. Yuan, et al., Green Chem. 19 (2017) 5559-5563;
  (c) T. Guo, X.N. Wei, Y. Liu, P.K. Zhang, Y.H. Zhao, Org. Chem. Front. 6 (2019) 1414-1422;
  (d) P. Ni, J. Tan, W. Zhao, et al., Org. Lett. 21 (2019) 3518-3522;
  (e) T. Guo, X.N. Wei, M. Zhang, et al., Chem. Commun. 56 (2020) 5751-5754;
  (f) X. Xu, D. Chen, Z. Wang, Chin. J. Org. Chem. 39 (2020) 3338-3352;
  (g) J. Zhang, H. Wang, Y. Chen, et al., Chin. Chem. Lett. 31 (2020) 1576-1579;
  (h) P. Ni, J. Tan, W. Zhao, H. Huang, G.J. Deng, Adv. Synth. Catal. 361 (2019) 5351-5356.
4. [4]
  (a) M. Sosnowska, S. Makurat, M. Zdrowowicz, J. Rak, J. Phys. Chem. B 121 (2017) 6139-6147;
  (b) D. Bartolini, L. Sancineto, A. Fabro de Bem, et al., Selenocompounds in cancer therapy: an overview, in: K.D. Tew, F. Galli (Eds.), Advances in Cancer Research, Vol. 136, Academic Press, 2017, pp. 259-302;
  (c) S. Makurat, M. Zdrowowicz, L. Chomicz-Mańka, et al., RSC Adv. 8 (2018) 21378-21388.
5. [5]
  (a) K. Anzai, J. Heterocycl. Chem. 16 (1979) 567-569;
  (b) A. Jana, A.K. Panday, R. Mishra, T. Parvin, L.H. Choudhury, ChemistrySelect 2 (2017) 9420-9424;
  (c) D.H. Lee, Y.H. Kim, Synlett 1995 (1995) 349-350;
  (d) X.D. Li, Y.T. Gao, Y.J. Sun, et al., Org. Lett. 21 (2019) 6643-6647.
6. [6]
  (a) K. Sun, X. Wang, F. Fu, et al., Green Chem. 19 (2017) 1490-1493;
  (b) W. Wei, H. Cui, H. Yue, D. Yang, Green Chem. 20 (2018) 3197-3202;
  (c) K. Sun, Z. Shi, Z. Liu, et al., Org. Lett. 20 (2018) 6687-6690;
  (d) D. Yang, G. Li, C. Xing, et al., Org. Chem. Front. 5 (2018) 2974-2979;
  (e) J. Hua, Z. Fang, J. Xu, et al., Green Chem. 21 (2019) 4706-4711;
  (f) K. Sun, S. Wang, R. Feng, et al., Org. Lett. 21 (2019) 2052-2055;
  (g) X.L. Ma, Q. Wang, X.Y. Feng, et al., Green Chem. 21 (2019) 3547-3551;
  (h) B. Huang, Y. Li, C. Yang, W. Xia, Green Chem. 22 (2020) 2804-2809;
  (i) J. Hua, Z. Fang, M. Bian, et al., ChemSusChem 13 (2020) 2053-2059.
7. [7]
  (a) J. Wen, L. Zhang, X. Yang, et al., Green Chem. 21 (2019) 3597-3601;
  (b) S. Zhang, L. Li, J. Zhang, et al., Chem. Sci. 10 (2019) 3181-3185;
  (c) H. Wang, J. Shi, J. Tan, et al., Org. Lett. 21 (2019) 9430-9433;
  (d) X. Kong, Y. Liu, L. Lin, Q. Chen, B. Xu, Green Chem. 21 (2019) 3796-3801;
  (e) J. Zhou, X.Z. Tao, J.J. Dai, et al., Chem. Commun. 55 (2019) 9208-9211;
  (f) C. Wan, R.J. Song, J.H. Li, Org. Lett. 21 (2019) 2800-2803;
  (g) G.Y. Dou, Y.Y. Jiang, K. Xu, C.C. Zeng, Org. Chem. Front. 6 (2019) 2392-2397;
  (h) Y.Z. Yang, R.J. Song, J.H. Li, Org. Lett. 21 (2019) 3228-3231;
  (i) Z. Zhang, J. Yan, D. Ma, J. Sun, Chin. Chem. Lett. 30 (2019) 1509-1511;
  (j) H. Ding, K. Xu, C.C. Zeng, J. Catal. 381 (2020) 38-43;
  (k) J.Y. Chen, H.Y. Wu, Q.W. Gui, et al., Org. Lett. 22 (2020) 2206-2209;
  (l) X. Meng, Y. Zhang, J. Luo, et al., Org. Lett. 22 (2020) 1169-1174;
  (m) M.X. He, Z.Y. Mo, Z.Q. Wang, et al., Org. Lett. 22 (2020) 724-728;
  (n) L.B. Zhang, R.S. Geng, Z.C. Wang, et al., Green Chem. 22 (2020) 16-21;
  (o) T.S. Zhang, W.J. Hao, R. Wang, et al., Green Chem. 22 (2020) 4259-4269;
  (p) J. Zhong, Y. Yu, D. Zhang, K. Ye, Chin. Chem. Lett. (2020), doi: http://dx.doi.org/10.1016/j.cclet.2020.08.011.
8. [8]
  (a) L.H. Lu, Z. Wang, W. Xia, et al., Chin. Chem. Lett. 30 (2019) 1237-1240;
  (b) L.Y. Xie, T.G. Fang, J.X. Tan, et al., Green Chem. 21 (2019) 3858-3863;
  (c) W.H. Bao, Z. Wang, X. Tang, et al., Chin. Chem. Lett. 30 (2019) 2259-2262;
  (d) W.B. He, L.Q. Gao, X.J. Chen, et al., Chin. Chem. Lett. 31 (2020) 1895-1898;
  (e) K.J. Liu, J.H. Deng, T.Y. Zeng, et al., Chin. Chem. Lett. 31 (2020) 1868-1872;
  (f) L.Y. Xie, Y.S. Bai, X.Q. Xu, et al., Green Chem. 22 (2020) 1720-1725;
  (g) L.Y. Xie, S. Peng, T.G. Fan, et al., Sci. China Chem. 62 (2019) 460-464.
9. [9]
  K. Van Aken, L. Strekowski, L. Patiny, Beilstein J. Org. Chem. 2 (2006) 3-9.
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1.
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