SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 7: 2089 - 2097

DOI: https://doi.org/10.6023/cjoc202203001

研究论文

银催化三氟甲硫基化-环化-水解: 含F3CS基喹啉酮合成

  • 李猛 ,
  • 孙凯
展开
  • a淄博职业学院制药与生物工程系 山东淄博 255300
    b烟台大学化学化工学院 山东烟台 264005

收稿日期: 2022-03-01

  修回日期: 2022-04-03

  网络出版日期: 2022-04-22

基金资助

国家自然科学基金(21801007); 武陵山民族药解析与创制湖南省工程实验室开放基金(Hgxy2103)

收起

Silver-Mediated Trifluoromethylthiolation-Cyclization-Hydrolysis: Access to F3CS-Containing Quinolinones

  • Meng Li ,
  • Kai Sun
Expand
  • aDepartment of Pharmacy and Biotechnology, Zibo Vocational Institute, Zibo, Shandong 255300
    bCollege of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005
* E-mail:

Received date: 2022-03-01

  Revised date: 2022-04-03

  Online published: 2022-04-22

Supported by

National Natural Science Foundation of China(21801007); Aid Program from Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wunlin Mountains(Hgxy2103)

Fold

摘要

以氰基作为自由基受体, 开发了一种实用的银催化三氟甲硫化/环化/水解策略. 在中等到较高产率的条件下, 获得了各种结构多样的F3CS-取代喹啉酮类化合物. 该方法易于放大量制备, 且产物具有进一步衍生化的潜力. 因此, 对制备其他有价值的含氟砌块的氮杂环化合物很有吸引力. 机理研究表明, 该催化体系涉及自由基途径, H2O在水解过程中起着不可或缺的作用.

关键词： 三氟甲硫基化; 氮杂环; 环化; 自由基; 衍生化

本文引用格式

李猛 , 孙凯 . 银催化三氟甲硫基化-环化-水解: 含F3CS基喹啉酮合成[J]. 有机化学, 2022 , 42(7) : 2089 -2097 . DOI: 10.6023/cjoc202203001

Abstract

Herein, a practical formal silver-mediated trifluoromethylthiolation cyclization hydrolysis protocol was developed with the cyano group as a radical acceptor. Various structurally diverse F3CS-substituted quinolinones were obtained in moderate to high yields. Easy scale-up operation and the potential for product derivatization make this method attractive for the preparation of other valuable F3CS-containing N-heterocycles. Mechanistic studies suggest that the catalytic system involves a radical pathway and H2O plays an indispensable role in the hydrolysis process.

Key words： trifluoromethylthiolation; N-heterocycles; cyclization; radical; derivatization

参考文献

[1]
(a) Mu?ller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[1]
(b) Hird, M. Chem. Soc. Rev. 2007, 36, 2070.
[1]
(c) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, S. V. Chem. Soc. Rev. 2008, 37, 320.
[1]
(d) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[1]
(e) Wang, S.-W.; Yu, J.; Zhou, Q.-Y.; Chen, S.-Y.; Xu, Z.-H.; Tang, S. ACS Sustainable Chem. Eng. 2019, 7, 10154.
[1]
(f) Tang, S.; Yuan, L.; Deng, Y.-L.; Li, Z.-Z.; Wang, L.-N.; Huang, G.-X.; Sheng, R.-L. Tetrahedron Lett, 2017, 58, 329.
[2]
(a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525.
[2]
(b) Yagupol’skii, L. M.; Il’chenko, A. Y.; Kondratenko, N. V. Russ. Chem. Rev. 1974, 43, 1.
[2]
(c) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
[2]
(d) Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827.
[2]
(e) Manteau, B.; Pazenok, S.; Vors, J. P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140.
[2]
(f) Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731.
[2]
(g) Ni, C.-F.; Hu, M.-Y. Hu, J.-B. Chem. Rev. 2015, 115, 765.
[2]
(h) Shao, X.-X.; Xu, C.-F.; Lu, L.; Shen, Q.-L. Acc. Chem. Res. 2015, 48, 1227.
[2]
(i) Chachignon, H.; Cahard, D. Chin J. Chem. 2016, 34, 445.
[3]
(a) Henkel, T.; Brunne, R. M.; Müller, H.; Reichel, F. Angew. Chem., Int. Ed. 1999, 38, 643.
[3]
(b) Hili, R.; Yudin, A. K. Nat. Chem. Biol. 2006, 2, 284.
[3]
(c) Gui, Q.-W.; Wang, B.-B.; Zhu, S.; Li, F.-L.; Zhu, M.-X.; Yi, M.; Yu, J.-L.; Wu, Z.-L.; He, W.-M. Green Chem. 2021, 23, 4430.
[4]
McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348.
[5]
(a) Zhang, S.-B.; Xu, X.-H.; Qing, F.-L. J. Fluorine Chem. 2019, 227, 109367.
[5]
(b) Liu, Y.-L.; Xu, X.-H.; Qing, F.-L. Adv. Synth. Catal. 2020, 362, 5031.
[6]
(a) Xiang, H.-Y.; Yang, C.-H. Org. Lett. 2014, 16, 21, 5686.
[6]
(b) Gelat, F.; Poisson, T.; Biju, A.T.; Pannecoucke, X.; Besset, T. Eur. J. Org. Chem. 2018, 2018, 3693.
[6]
(c) Zhu, D.; Luo, H.-Y.; Chen, Z.-M. Org. Lett. 2021, 23, 1044.
[7]
(a) Jin, D.-P.; Gao, P.; Gao, D.-Q.; Chen, S.; Wang, J.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 3486.
[7]
(b) Modak, A.; Pinter, E. N.; Cook, S. P. J. Am. Chem. Soc. 2019, 141, 18405.
[7]
(c) Zheng, C.-G.; Huang, S.-A.; Liu, Y.; Jiang, C.; Zhang, W.; Fang, G.; Hong, J.-Q. Org. Lett. 2020, 22, 4868.
[7]
(d) Yang, W.-C.; Zhang, M.-M.; Sun, Y.; Chen, C.-Y.; Wang, L. Org. Lett. 2021, 23, 6691.
[8]
(a) Tang, S.; Deng, Y.-L.; Li, J.; Wang, W.-X.; Wang, Y.-C.; Li, Z.-Z.; Yuan, L.; Chen, S.-L.; Sheng, R.-L. Chem. Commun. 2016, 52, 4470.
[8]
(b) Yu, J.; Sheng, H.-X.; Wang, S.-W.; Xu, Z.-H.; Tang, S.; Chen, S.-L. Chem. Commun. 2019, 55, 4578.
[8]
(c) Zhang, G.; Liu, Y.; Zhao, J.-B.; Li, Y.; Zhang, Q. Sci. China Chem. 2019, 62, 1476.
[8]
(c) Wu, X.-X.; Ma, Z.-G., Feng, T.-T.; Zhu, C. Chem. Soc. Rev. 2021, 50, 11577.
[9]
Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128.
[10]
Fuentes, N.; Kong, W.; Fernández-Sánchez, L.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2015, 137, 964.
[11]
Qiu, Y.-F.; Zhu, X.-Y.; Li, Y.-X.; He, Y.-T.; Yang, F.; Wang, J.; Hua, H.-L.; Zheng, L.; Wang, L.-C.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2015, 17, 3694.
[12]
Guo, K.; Zhang, H.-L.; Cao, S.-J.; Gu, C.; Zhou, H.-T.; Li, J.; Zhu, Y.-G. Org. Lett. 2018, 20, 2261.
[13]
Sun, K.; Lv, Q.-Y.; Lin, Y.-W.; Yu, B.; He, W.-M. Org. Chem. Front. 2021, 8, 445.
[14]
Fu, H.; Wang, S.-S.; Li, Y.-M. Adv. Synth. Catal. 2016, 358, 3616.
[15]
(a) Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100.
[15]
(b) Sun, K.; Li, Y.-L.; Feng, R.-R.; Mu, S.-Q.; Wang, X.; Zhang, B. J. Org. Chem. 2020, 85, 1001.
[15]
(c) Sun, K.; Lei, J.; Liu, Y.; Liu, B.; Chen, N. Adv. Synth. Catal. 2020, 362, 3709.
[15]
(d) Wang, X.; Guo, S.; Zhang, Y.; Zhang, Z.; Zhang, G.; Ye, Y.; Sun, K. Adv. Synth. Catal. 2021, 363, 3290.
[15]
(e) Wang, X.; Lei, J.; Guo, S.; Zhang, Y.; Ye, Y.; Tang, S.; Sun, K. Chem. Commun. 2022, 58, 1526.
[15]
(f) Zhang, Z.; Wang, S.-L.; Tan, P.-P.; Gu, X.-W.; Sun, W.-J.; Liu, C.; Chen, J.-C.; Li, J.-Z.; Sun, K. Org. Lett. 2022, 24, 12, 2288.
[16]
(a) Hu, M.; Fan, J.-H.; Liu, Y.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 9577.
[16]
(b) Wang, A.-F.; Zhu, L.-Y.; Wang, S.-L.; Hao, W.-J.; Li, G.-G.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2016, 81, 1099.
[16]
(c) Guo, Y.-H.; Xiang, Y.-F.; Wei, L.; Wan, J.-P. Org. Lett. 2018, 20, 3971.
[16]
(d) Li, G.-Q.; Gan, Z.-Y.; Kong, K.-X.; Dou, X.-M.; Yang, D.-S. Adv. Synth. Catal. 2019, 361, 1808.
[16]
(e) Song, S.-Z.; Meng, Y.-N.; Li, Q.; Wei, W.-T. Adv. Synth. Catal. 2020, 362, 2120.
Options
文章导航

/

〈 〉