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2020 , Vol. 40 >Issue 9: 2855 - 2862

DOI: https://doi.org/10.6023/cjoc202004051

研究论文

电化学促进的N-烯丙基硫代酰胺的硒化/环化合成2-噻唑啉

  • 潘超 ,
  • 刘鹏 ,
  • 武安国 ,
  • 李明 ,
  • 文丽荣 ,
  • 郭维斯
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  • 青岛科技大学化学与分子工程学院 生态化工国家重点实验室培育基地 山东青岛 266042

收稿日期: 2020-04-30

  修回日期: 2020-06-07

  网络出版日期: 2020-06-19

基金资助

国家自然科学基金（No.21572110）、山东省自然科学基金（No.ZR2019MB010）和国家级大学生创新创业训练计划（No.201910426037）资助项目.

收起

Electrochemical-Promoted Synthesis of 2-Thiazolines via Selenylation/Cyclization of N-Allylthioamides

  • Pan Chao ,
  • Liu Peng ,
  • Wu An'guo ,
  • Li Ming ,
  • Wen Lirong ,
  • Guo Weisi
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  • State Key Laboratory Base of Eco-chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042

Received date: 2020-04-30

  Revised date: 2020-06-07

  Online published: 2020-06-19

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572110), the Natural Science Foundation of Shandong Province (No. ZR2019MB010) and the National College Student's Innovation and Entrepreneurship Training Program (No. 201910426037).

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摘要

建立了一种电化学促进N-烯丙基硫代酰胺的串联硒化/环化新方法，用来制备含硒官能团的2-噻唑啉衍生物.该方法反应条件温和，底物范围广.初步的机理研究表明，反应过程中有硒自由基的参与.该方法操作简单且无需使用催化剂、过渡金属和氧化剂.

关键词： 电合成; 噻唑啉; 硫代酰胺; 硒化

本文引用格式

潘超 , 刘鹏 , 武安国 , 李明 , 文丽荣 , 郭维斯 . 电化学促进的N-烯丙基硫代酰胺的硒化/环化合成2-噻唑啉[J]. 有机化学, 2020 , 40(9) : 2855 -2862 . DOI: 10.6023/cjoc202004051

Abstract

An electrochemical selenylation/cyclization of N-allylthioamides has been developed for the synthesis of selenium-containing 2-thiazolines. This protocol provides an efficient approach to produce 2-thiazolines with broad substrate scope under mild reaction conditions. Preliminary mechanistic study indicates that selenium radical may be involved. The reaction is easy operated under catalyst- and oxidant-free conditions.

Key words： electrosynthesis; thiazolines; thioamides; selenation

参考文献

[1] (a) Yuichi, O.; Yuichi, M.; Masahito, Y.; Takayuki, D. J. Med. Chem. 2017, 60, 6751.
(b) Conley, N. R.; Andrasi, A.-D.; Rao, J.; Moerner, W. E. Angew. Chem.. Int. Ed. 2012, 51, 3350.
(c) Marson, C. M.; Matthews, C. J.; Yiannaki, E.; Atkinson, S. J.; Soden, P. E.; Shukla, L.; Lamadema, N.; Thomas, N. S. B. J. Med. Chem. 2013, 56, 6156.
(d) Altıntop, M. D.; Kaplancıklı, Z. A.; Çiftçi, G. A.; Demirel, R. Eur. J. Med. Chem. 2014, 74, 264.
[2] (a) Du, D.-M.; Lu, S.-F.; Fang, T.; Xu, J. J. Org. Chem. 2005, 70, 3712.
(b) Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133.
(c) Liu, L.; Li, J.; Wang, M.; Du, F.; Qin, Z.; Fu, B. Tetrahedron. Asymmetry 2011, 22, 550.
[3] (a) Alom, N. E.; Wu, F.; Li, W. Org. Lett. 2017, 19, 930.
(b) Gaumont, A. C.; Gulea, M.; Levillain, J. Chem. Rev. 2009, 109, 1371.
(c) Jeon, H.; Kim D.; Lee, J. H.; Song J.; Lee, W. S.; Kang, D. W.; Kang, S.; Lee, S. B.; Choi, S.; Hong, K. B. Adv. Synth. Catal. 2018, 360, 779.
[4] (a) Trose, M.; Lazreg, F.; Lesieur, M.; Cazin, C. S. J. Green Chem. 2015, 17, 3090.
(b) Maltsev, O. V.; Walter, V.; Brandl, M. J.; Hintermann, L. Synthesis 2013, 45, 2763.
[5] (a) Qumruddeen; Yadav, A.; Kant, R.; Tripathi, C. B. J. Org. Chem. 2020, 85, 2814.
(b) Morse, P. D.; Nicewicz, D. A. Chem. Sci. 2015, 6, 270.
(c) Liu, G.-Q.; Yang, C.-H.; Li, Y.-M. J. Org. Chem. 2015, 80, 11339.
[6] Shao, L.; Li, Y.; Lu, J.; Jiang, X. Org. Chem. Front. 2019, 6, 2999.
[7] (a) Seng, H.-L.; Tiekink, E. R. T. Appl. Organomet. Chem. 2012, 26, 655.
(b) Sahu,.P. K.; Umme, T.; Yu, J.; Nayak, A.; Kim, G.; Noh, M.; Lee, J.-Y.; Kim, D.-D.; Jeong, L. S. J. Med. Chem. 2015, 58, 8734.
(c) Nogueira, C. W.; Zeni, G.; Rocha. J. B. T. Chem. Rev. 2004, 104, 6255.
[8] (a) Engman, L. J. Org. Chem. 1991, 56, 3425.
(b) Sahoo, H.; Singh, S.; Baidya, M. Org. Lett. 2018, 20, 3678.
(c) Wang, X.; Mu, S.; Sun, T.; Sun, K. Chin. J. Org. Chem. 2019, 39, 2802(in Chinese). (王薪, 穆石强, 孙婷, 孙凯, 有机化学, 2019, 39, 2802.)
(d) Wang, M.; Wu, Z.; Zhu, C. Org. Chem. Front. 2017, 4, 427.
(e) Reddy, C. R.; Ranjan, R.; Prajapti, S. K. Org. Lett. 2019, 21, 623.
[9] Zhang, Q.-B.; Yuan, P.-F.; Kai, L.-L.; Liu, K.; Ban, Y.-L.; Wang, X.-Y.; Wu, L.-Z.; Liu, Q. Org. Lett. 2019, 21, 885.
[10] Yu, J.-M.; Cai, C. Org. Biomol. Chem. 2018, 16, 490.
[11] Casola, K. K.; Back, D. F.; Zeni, G. J. Org. Chem. 2015, 80, 7702.
[12] Sun, K.; Wang, S.; Feng, R.; Zhang, Y.; Wang, X.; Zhang, Z.; Zhang, B. Org. Lett. 2019, 21, 2052.
[13] (a) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339.
(b) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309.
(c) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485.
(d) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
[14] (a) Adeli, Y.; Huang, K.-M.; Liang, Y.-J.; Jiang, Y.-Y.; Liu, J.-Z.; Song, S.; Zeng, C.-C.; Jiao, N. ACS Catal. 2019, 9, 2063.
(b) Huang, M.; Dai, J.; Cheng, X.; Ding, M. Org. Lett. 2019, 21, 7759.
(c) Lian, F.; Sun, C.; Xu, K.; Zeng, C. Org. Lett. 2019, 21, 156.
(d) Zhang, S.; Li, L.; Xue, M.; Zhang, R.; Xu, K.; Zeng, C. Org. Lett. 2018, 20, 3443.
(e) Huang, C.; Qian, X.-Y.; Xu, H.-C. Angew. Chem.. Int. Ed. 2019, 58, 6650.
(f) Feng, E.-Q.; Hou, Z.-W.; Xu, H.-C. Chin. J. Org. Chem. 2019, 39, 1424(in Chinese). (冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39, 1424.)
(g) Hou, Z.-W.; Xu, H.-C. Chin. J. Chem. 2020, 38, 394.
(h) Liu, W.-Q.; Yang, X.-L.; Tung, C.-H.; Wu, L.-Z. Acta Chim. Sinica 2019, 77, 861(in Chinese). (刘文强, 杨修龙, 佟振合, 吴骊珠, 化学学报, 2019, 77, 861.)
[15] (a) Li, Q.-Y.; Cheng, S.-Y.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2019, 21, 5517.
(b) Cao, Y.; Yuan, Y.; Lin, Y.; Jiang, X.; Weng, Y.; Wang, T.; Bu, F.; Zeng, L.; Lei, A. Green Chem. 2020, 22, 1548.
(c) Meng, X.-J.; Zhong, P.-F.; Wang, Y.-M.; Wang, H.-S.; Tang, H.-T.; Pan, Y.-M. Adv. Synth. Catal. 2020, 362, 506.
(d) He, M.-X.; Mo, Z.-Y.; Wang, Z.-Q.; Cheng, S.-Y.; Xie, R.-R.; Tang, H.-T.; Pan, Y.-M. Org. Lett. 2020, 22, 724.
(e) Wang, Z.-Q.; Meng, X.-J.; Li, Q.-Y.; Tang, H.-T.; Wang, H.-S.; Pan, Y.-M. Adv. Synth. Catal. 2018, 360, 4043.
(f) Zhang, Z.; Zhang, L.; Cao, Y.; Li, F.; Bai, G.; Liu, G.; Yang, Y.; Mo, F. Org. Lett. 2019, 21, 762.
(g) Wang, Z.-Q.; Hou, C.; Zhong, Y.-F.; Lu, Y.-X.; Mo, Z.-Y.; Pan, Y.-M.; Tang, H.-T. Org. Lett. 2019, 21, 9841.
(h) Li, D.; Seavill, P. W.; Wilden, D. J. D. ChemElectroChem 2019, 6, 5829.
[16] Sun, L.; Yuan, Y.; Yao, M.; Wang, H.; Wang, D.; Gao, M.; Chen, Y.-H.; Lei, A. Org. Lett. 2019, 21, 1297.
[17] Guan, Z.; Wang, Y.; Wang, H.; Huang, Y.; Wang, S.; Tang, H.; Zhang, H.; Lei, A. Green Chem. 2019, 21, 4976.
[18] Mallick, S.; Baidya, M.; Mahanty, K.; Maiti, D.; Sarkar, S. D. Adv. Synth. Catal. 2020, 362, 1046.
[19] (a) Guo, W.-S.; Wen, L.-R.; Li, M. Org. Biomol. Chem. 2015, 13, 1942.
(b) Guo, W.-S.; Gong, H.; Zhang, Y.-A.; Wen, L.-R.; Li, M. Org. Lett. 2018, 20, 6394.
(c) Li, M.; Cao, H.; Wang, Y.; Lv, X.-L.; Wen, L.-R. Org. Lett. 2012, 14, 3470.
[20] (a) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.
(b) Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
(c) Qing, F. Chin. J. Org. Chem. 2012, 32, 815(in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.)
[21]
(d) Zhang, F.; Peng, X.; Ma, J. Chin. J. Org. Chem. 2019, 39, 109(in Chinese). (张发光, 彭星, 马军安, 有机化学, 2019, 39, 109.)
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