Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones

doi:10.6023/cjoc202107042

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4610-4622.DOI: 10.6023/cjoc202107042 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑；绿色合成化学专辑

REVIEWS

电化学条件下喹喔啉-2(1H)-酮C(3)—H功能化的研究进展

李丹丹^*(), 王晓辰, 李闪闪, 付晨雨, 李倩倩, 许东涛, 马莹莹

许昌学院化工与材料学院表面微纳米材料研究所河南省储能与转化微纳米材料重点实验室河南许昌 461000

收稿日期:2021-07-18 修回日期:2021-09-04 发布日期:2021-09-14
通讯作者: 李丹丹
基金资助:
国家自然科学基金(21901219); 河南教育厅重点项目(20B150024); 2021年度河南省高等教育青年骨干教师培养计划(2021GGJS146); 河南省药品质量控制与评价重点实验室(郑州大学)开放课题科研基金和许昌学院杰出青年骨干资助项目

Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones

Dandan Li(), Xiaochen Wang, Shanshan Li, Chenyu Fu, Qianqian Li, Dongtao Xu, Yingying Ma

Key Laboratory of Micro-Nano Materials for Energy Storage and Conversion of Henan Province, Institute of Surface Micro and Nano Materials, College of Chemical and Materials Engineering, Xuchang University, Xuchang, Henan 461000

Received:2021-07-18 Revised:2021-09-04 Published:2021-09-14
Contact: Dandan Li
Supported by:
National Natural Science Foundation of China(21901219); Key Project of Education Department of Henan Province(20B150024); Young Key Teacher Training Plan of Henan Provincial Higher Education in 2021(2021GGJS146); Open Subject Research Fund of the Key Laboratory of Drug Quality Control and Evaluation in Henan Province and the Young Backbone Teachers Project of Xuchang University

Quinoxalinone and its derivatives are a class of important nitrogen heterocyclic compounds, which widely exist in natural products, drugs and functional materials. Therefore, the C—H functionalization of quinoxalinone has attracted extensive attention of chemical workers. In recent years, electrochemical synthesis directly uses electron as a “clean reagent” to participate in redox reaction without additional redox reagent, which has the characteristics of mild reaction conditions and good atom economy. This method meets the requirements of green chemistry and sustainable development. With the in-depth study on the mechanism of electrochemical synthesis and the standardization of reaction equipment, this method has become a powerful tool for functionalization of quinoxalineones. The recent advances in the electrochemical C(3)—H functionalization of quinoxaline-2(1H)-one are summarized. The reaction transformation conditions and mechanisms are systematically discussed, and the challenges and future directions of this field are included.

Key words: electrochemical synthesis, quinoxalin-2(1H)-one, C(3)—H functionalization

Cite this article

Dandan Li, Xiaochen Wang, Shanshan Li, Chenyu Fu, Qianqian Li, Dongtao Xu, Yingying Ma. Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4610-4622.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 27

Scheme 1. Reaction pathways for electrochemical C(3)—H functionalization of quinoxalin-2-ones

Scheme 2. Nickel-catalyzed electrochemical reductive decarboxylative coupling of N-hydroxyphthalimide esters with quinoxalinones

Scheme 3. Possible mechanism

Scheme 4. Electrochemical decarboxylative C(3) alkylation of quinoxalin-2(1H)-ones

Scheme 5. Possible mechanism

Scheme 6. Electrochemical oxidative C—H alkylation of quinoxalin-2(1H)-ones with organoboron compounds

Scheme 7. Possible mechanism

Scheme 8. Electrochemical deoxygenative alkylation of quinoxalin-2(1H)-ones with alkyl carbazates

Scheme 9. Possible mechanism

Scheme 10. Electrochemical cross-coupling of C(sp2)—H with aryldiazonium salts via a paired electrolysis

Scheme 11. Possible mechanism

Scheme 12. Electrochemical heteroarylation of quinoxalin- 2(1H)-ones with pyrroles

Scheme 13. Electroreductive-induced C(3) pyridylation of quinoxalin-2(1H)-ones with cyanopyridines

Scheme 14. Possible mechanism

Scheme 15. Bromide ions-mediated electrosynthesis of Minisci- type trifluoromethylation of quinoxaline-2(1H)-ones

Scheme 16. Possible mechanism

Scheme 17. Electrooxidative C(3) cyanation of quinoxalin- 2(1H)-ones with TMSCN

Scheme 18. Possible mechanism

Scheme 19. Electro-oxidative C(3)—H amination of quinoxalin-2(1H)-ones

Scheme 20. Possible mechanism

Scheme 21. Electrochemical dehydrogenative C—H/O—H cross-coupling for the synthesis of 3-alkoxylated quinoxalin-2(1H)-ones

Scheme 22. Possible mechanism

Scheme 23. Electrooxidative cross-coupling for the synthesis of 3-thioquinoxalinones

Scheme 24. Possible mechanism

Scheme 25. Electrochemical phosphonation of quinoxalin-2(1H)-ones via C—H/P—H dehydrogenative cross-coupling

Scheme 26. Possible mechanism

Scheme 27. Electrochemical oxidative coupling of quinoxalin-2(1H)-ones with diarylphosphine oxides

References 30

[1]	(a) Waring, M. J.; Ben-Hadda, T.; Kotchevar, A. T.; Ramdani, A.; Touzani, R.; Elkadiri, S.; Hakkou, A.; Bouakka, M.; Ellis, T. Molecules 2002, 7, 641. doi: 10.3390/70800641 pmid: 24793885
	(b) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. doi: 10.1021/cr020033s pmid: 24793885
	(c) Refaat, H. M.; Moneer, A. A.; Khalil, O. M. Arch. Pharm. Res. 2004, 27, 1093. pmid: 24793885
	(d) Carta, A.; Piras, S.; Loriga, G.; Paglietti, G. Mini-Rev. Med. Chem. 2006, 6, 1179. pmid: 24793885
	(e) El-Hawash, S. A. M.; Habib, N. S.; Kassem, M. A. Arch. Pharm. 2006, 339, 564. pmid: 24793885
	(f) Meyer, E.; Joussef, A. C.; de Souza, L. D. B. P. Synth. Commun. 2006, 36, 729. doi: 10.1080/00397910500447066 pmid: 24793885
	(g) Moarbess, G.; Deleuze-Masquefa, C.; Bonnard, V.; Gayraud- Paniagua, S.; Vidal, J.-R.; Bressolle, F.; Pinguet, F.; Bonnet, P.-A. Bioorg. Med. Chem. 2008, 16, 6601. doi: 10.1016/j.bmc.2008.05.022 pmid: 24793885
	(h) Ramli, Y.; Benzeid, H.; Bouhfid, R.; Rodi, Y. K.; Ferfra, S.; Essassi, E. M. Stud. Cercet. Stiint.: Chim. Ing. Chim., Biotehnol., nd. Aliment. 2010, 11, 67. pmid: 24793885
	(i) Liu, R.; Huang, Z.; Murray, M. G.; Guo, X.; Liu, G. J. Med. Chem. 2011, 54, 5747. doi: 10.1021/jm200394x pmid: 24793885
	(j) Galal, S. A.; Khairat, S. H. M.; Ragab, F. A. F.; Abdelsamie, A. S.; Ali, M. M.; Soliman, S. M.; Mortier, J.; Wolber, G.; El Diwani, H. I. Eur. J. Med. Chem. 2014, 86, 122. doi: 10.1016/j.ejmech.2014.08.048 pmid: 24793885
	(k) Hussain, S.; Parveen, S.; Hao, X.; Zhang, S.; Wang, W.; Qin, X.; Yang, Y.; Chen, X.; Zhu, S.; Zhu, C.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383. doi: 10.1016/j.ejmech.2014.04.047 pmid: 24793885
	(l) Khattab, S. N.; Abdel Moneim, S. A. H.; Bekhit, A. A.; El Massry, A. M.; Hassan, S. Y.; El-Faham, A.; Ali Ahmed, H. E.; Amer, A. Eur. J. Med. Chem. 2015, 93, 308. doi: 10.1016/j.ejmech.2015.02.020 pmid: 24793885
	(m) Qin, X.; Hao, X.; Han, H.; Zhu, S.; Yang, Y.; Wu, B.; Hussain, S.; Parveen, S.; Jing, C.; Ma, B.; Zhu, C. J. Med. Chem. 2015, 58, 1254. doi: 10.1021/jm501484b pmid: 24793885
	(n) Cil, O.; Phuan, P.-W.; Lee, S.; Tan, J.; Haggie, P. M.; Levin, M. H.; Sun, L.; Thiagarajah, J. R.; Ma, T.; Verkman, A. S. Cell Mol. Gastroenterol. Hepatol. 2016, 2, 317. doi: 10.1016/j.jcmgh.2015.12.010 pmid: 24793885
	(o) Shi, L.; Li, X.; Hu, W.; Wu, J.; Zhou, H.; Zhou, H. Mini-Rev. Med. Chem. 2018, 18, 392. doi: 10.2174/1389557517666171101111134 pmid: 24793885
[2]	Weïwer, M.; Spoonamore, J.; Wei, J.; Guichard, B.; Ross, N. T.; Masson, K.; Silkworth, W.; Dandapani, S.; Palmer, M.; Scherer, C. A.; Stern, A. M.; Schreiber, S. L.; Munoz, B. ACS Med. Chem. Lett. 2012, 3, 1034. doi: 10.1021/ml300246r
[3]	(a) Smits, R. A.; Lim, H. D.; Hanzer, A.; Zuiderveld, O. P.; Guaita, E.; Adami, M.; Coruzzi, G.; Leurs, R.; de Esch, I. J. P. J. Med. Chem. 2008, 51, 2457. doi: 10.1021/jm7014217 pmid: 22639721
	(b) Abu-Hashem, A. A.; Gouda, M. A.; Badria, F. A. Eur. J. Med. Chem. 2010, 45, 1976. doi: 10.1016/j.ejmech.2010.01.042 pmid: 22639721
	(c) Mangold, S. L.; Prost, L. R.; Kiessling, L. L. Chem. Sci. 2012, 3, 772. pmid: 22639721
[4]	Quinn, J.; Guo, C.; Ko, L.; Sun, B.; He, Y.; Li, Y. RSC Adv. 2016, 6, 22043. doi: 10.1039/C5RA26227E
[5]	(a) Xie, L.-Y.; Bai, Y.-S.; Xu, X.-Q.; Peng, X.; Tang, H.-S.; Huang, Y.; Lin, Y.-W.; Cao, Z.; He, W.-M. Green Chem. 2020, 22, 1720. doi: 10.1039/C9GC03899J
	(b) Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189. (in Chinese) doi: 10.6023/cjoc201807014
	( 王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.) doi: 10.6023/cjoc201807014
	(c) Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950. doi: 10.1039/D1GC00562F
	(d) Shi, J.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese) doi: 10.6023/cjoc202000041
	( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.) doi: 10.6023/cjoc202000041
	(e) Mao, P.; Zhu, J.; Yuan, J.; Yang, L.; Xiao, Y.; Zhang, C. Chin. J. Org. Chem. 2019, 39, 1529. (in Chinese) doi: 10.6023/cjoc201904025
	( 毛璞, 朱军亮, 袁金伟, 杨亮茹, 肖咏梅, 张长森, 有机化学, 2019, 39, 1529.) doi: 10.6023/cjoc201904025
	(f) Xie, L.-Y.; Peng, S.; Yang, L.-H.; Peng, C.; Lin, Y.-W.; Yu, X.; Cao, Z.; Peng, Y.-Y.; He, W.-M. Green Chem. 2021, 23, 374. doi: 10.1039/D0GC02844D
	(g) Yi, R.; He, W. Chin. J. Org. Chem. 2021, 41, 1267. (in Chinese) doi: 10.6023/cjoc202100022
	( 易荣楠, 何卫民, 有机化学, 2021, 41, 1267.) doi: 10.6023/cjoc202100022
	(h) Xie, L.-Y.; Liu, Y.-S.; Ding, H.-R.; Gong, S.-F.; Tan, J.-X.; He, J.-Y.; Cao, Z.; He, W.-M. Chin. J. Catal. 2020, 41, 1168. doi: 10.1016/S1872-2067(19)63526-6
	(i) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Yan, S.-S.; Deng, J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. J. Catal. 2021, 42, 1445. doi: 10.1016/S1872-2067(20)63750-0
	(j) Ke, Q.; Yan, G.; Yu, J.; Wu, X. Org. Biomol. Chem. 2019, 17, 5863. doi: 10.1039/C9OB00782B
	(k) Rostoll-Berenguer, J.; Blay, G.; Pedro, J. R.; Vila, C. Eur. J. Org. Chem. 2020, 2020, 6148. doi: 10.1002/ejoc.v2020.39
	(l) Monika, M.; Selvakumar, S. Synthesis 2019, 51, 4113. doi: 10.1055/s-0037-1611910
	(m) Ghosh, P.; Das, S. Synth. Commun. 2020, 50, 2266. doi: 10.1080/00397911.2020.1765257
[6]	(a) Frontana-Uribe, B. A.; Little, R. D.; Ibanez, J. G.; Palma, A.; Vasquez-Medrano, R. Green Chem. 2010, 12, 2099. doi: 10.1039/c0gc00382d
	(b) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485. doi: 10.1021/acs.chemrev.7b00271
	(c) Jiao, K.-J.; Xing, Y.-K.; Yang, Q.-L.; Qiu, H.; Mei, T.-S. Acc. Chem. Res. 2020, 53, 300. doi: 10.1021/acs.accounts.9b00603
	(d) Karkas, M. D. Chem. Soc. Rev. 2018, 47, 5786. doi: 10.1039/C7CS00619E
	(e) Ma, C.; Fang, P.; Mei, T.-S. ACS Catal. 2018, 8, 7179. doi: 10.1021/acscatal.8b01697
	(f) Maeda, H.; Ohmori, H. Acc. Chem. Res. 1999, 32, 72. doi: 10.1021/ar970329y
	(g) Minteer, S. D.; Baran, P. Acc. Chem. Res. 2020, 53, 545. doi: 10.1021/acs.accounts.0c00049
	(h) Möhle, S.; Zirbes, M.; Rodrigo, E.; Gieshoff, T.; Wiebe, A.; Waldvogel, S. R. Angew. Chem., nt. Ed. 2018, 57, 6018.
	(i) Novaes, L. F. T.; Liu, J.; Shen, Y.; Lu, L.; Meinhardt, J. M.; Lin, S. Chem. Soc. Rev. 2021, 50, 7941. doi: 10.1039/D1CS00223F
	(j) Röckl, J. L.; Pollok, D.; Franke, R.; Waldvogel, S. R. Acc. Chem. Res. 2020, 53, 45. doi: 10.1021/acs.accounts.9b00511
	(k) Sauermann, N.; Meyer, T. H.; Qiu, Y.; Ackermann, L. ACS Catal. 2018, 8, 7086. doi: 10.1021/acscatal.8b01682
	(l) Waldvogel, S. R.; Lips, S.; Selt, M.; Riehl, B.; Kampf, C. J. Chem. Rev. 2018, 118, 6706. doi: 10.1021/acs.chemrev.8b00233
	(m) Wang, H.; Gao, X.; Lv, Z.; Abdelilah, T.; Lei, A. Chem. Rev. 2019, 119, 6769. doi: 10.1021/acs.chemrev.9b00045
	(n) Yamamoto, K.; Kuriyama, M.; Onomura, O. Acc. Chem. Res. 2020, 53, 105. doi: 10.1021/acs.accounts.9b00513
	(o) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397
	(p) Yi, H.; Zhang, G.; Wang, H.; Huang, Z.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016. doi: 10.1021/acs.chemrev.6b00620
	(q) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309. doi: 10.1021/acs.accounts.9b00512
[7]	Tan, Y.; Wang, J.; Zhang, H.-Y.; Zhang, Y.; Zhao, J. Front. Chem. 2020, 8, 582. doi: 10.3389/fchem.2020.00582
[8]	Lian, F.; Xu, K.; Meng, W.; Zhang, H.; Tan, Z.; Zeng, C. Chem. Commun. 2019, 55, 14685. doi: 10.1039/C9CC07840A
[9]	Niu, K.; Song, L.; Hao, Y.; Liu, Y.; Wang, Q. Chem. Commun. 2020, 56, 11673. doi: 10.1039/D0CC05391K
[10]	Traister, K. M.; Molander, G. A. Synthesis and Application of Organoboron Compounds, In Topics in Organometallic Chemistry, Vol. 49, Eds.: Fernández, E.; Whiting, A., Springer, Switzerland, 2015, pp. 117-151.
[11]	Niu, K.; Hao, Y.; Song, L.; Liu, Y.; Wang, Q. Green Chem. 2021, 23, 302. doi: 10.1039/D0GC03892J
[12]	Gao, Y.; Wu, Z.; Yu, L.; Wang, Y.; Pan, Y. Angew. Chem., nt. Ed. 2020, 59, 10859.
[13]	Mo, F.; Qiu, D.; Zhang, L.; Wang, J. Chem. Rev. 2021, 121, 5741. doi: 10.1021/acs.chemrev.0c01030
[14]	Jiang, Y.-Y.; Dou, G.-Y.; Zhang, L.-S.; Xu, K.; Little, R. D.; Zeng, C.-C. Adv. Synth. Catal. 2019, 361, 5170. doi: 10.1002/adsc.v361.22
[15]	Hu, C.; Hong, G.; Zhou, C.; Tang, Z.-C.; Han, J.-W.; Wang, L.-M. Asian J. Org. Chem. 2019, 8, 2092. doi: 10.1002/ajoc.v8.11
[16]	(a) Lehnherr, D.; Lam, Y.-H.; Nicastri, M. C.; Liu, J.; Newman, J. A.; Regalado, E. L.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2020, 142, 468. doi: 10.1021/jacs.9b10870 pmid: 33861088
	(b) Nicastri, M. C.; Lehnherr, D.; Lam, Y.-H.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2020, 142, 987. doi: 10.1021/jacs.9b10871 pmid: 33861088
	(c) Zhang, S.; Li, L.; Li, X.; Zhang, J.; Xu, K.; Li, G.; Findlater, M. Org. Lett. 2020, 22, 3570. doi: 10.1021/acs.orglett.0c01014 pmid: 33861088
	(d) Zhang, X.; Yang, C.; Gao, H.; Wang, L.; Guo, L.; Xia, W. Org. Lett. 2021, 23, 3472. doi: 10.1021/acs.orglett.1c00920 pmid: 33861088
[17]	Wen, J.; Yang, X.; Yan, K.; Qin, H.; Ma, J.; Sun, X.; Yang, J.; Wang, H. Org. Lett. 2021, 23, 1081. doi: 10.1021/acs.orglett.0c04296
[18]	(a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. doi: 10.1039/B610213C pmid: 21456523
	(b) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455. doi: 10.1021/cr100166a pmid: 21456523
	(c) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475. doi: 10.1021/cr1004293 pmid: 21456523
	(d) Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 2012, 6679. doi: 10.1002/ejoc.v2012.34 pmid: 21456523
[19]	Dou, G.-Y.; Jiang, Y.-Y.; Xu, K.; Zeng, C.-C. Org. Chem. Front. 2019, 6, 2392. doi: 10.1039/C9QO00552H
[20]	(a) Scheuer, P. J. Acc. Chem. Res. 1992, 25, 433. doi: 10.1021/ar00022a001 pmid: 20804202
	(b) Fleming, F. Nat. Prod. Rep. 1999, 16, 597. doi: 10.1039/a804370a pmid: 20804202
	(c) Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. J. Med. Chem. 2010, 53, 7902. doi: 10.1021/jm100762r pmid: 20804202
[21]	(a) Larock, R. C. Comprehensive Organic Transformations, Wiley-VCH, New York, 1989, p. 819.
	(b) Caboni, P.; Sammelson, R. E.; Casida, J. E. J. Agric. Food Chem. 2003, 51, 7055. doi: 10.1021/jf030439l
	(c) Kuhn, P.; Thomas, A.; Antonietti, M. Macromolecules 2009, 42, 319. doi: 10.1021/ma802322j
[22]	(a) Liskey, C. W.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11389. doi: 10.1021/ja104442v pmid: 20677758
	(b) Wade, J. R. Organic Chemistry, 8 th ed., Pearson Education Inc, Glenview, Illinois, USA, 2013. pmid: 20677758
	(c) Zhang, S.; del Pozo, J.; Romiti, F.; Mu, Y.; Torker, S.; Hoveyda, A. H. Science 2019, 364, 45. doi: 10.1126/science.aaw4029 pmid: 20677758
[23]	Zhan, Y.; Li, Y.; Tong, J.; Liu, P.; Sun, P. Eur. J. Org. Chem. 2021, 2021, 2193.
[24]	(a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b pmid: 26507237
	(b) Cernak, T.; Dykstra, K. D.; Tyagarajan, S.; Vachal, P.; Krska, S. W. Chem. Soc. Rev. 2016, 45, 546. doi: 10.1039/c5cs00628g pmid: 26507237
[25]	Li, K.-J.; Xu, K.; Liu, Y.-G.; Zeng, C.-C.; Sun, B.-G. Adv. Synth. Catal. 2019, 361, 1033. doi: 10.1002/adsc.v361.5
[26]	Jiang, X.; Yang, L.; Ye, Z.; Du, X.; Fang, L.; Zhu, Y.; Chen, K.; Li, J.; Yu, C. Eur. J. Org. Chem. 2020, 2020, 1687. doi: 10.1002/ejoc.201901928
[27]	Song, C.; Liu, K.; Dong, X.; Chiang, C.-W.; Lei, A. Synlett 2019, 30, 1149. doi: 10.1055/s-0037-1611753
[28]	Zhou, J.; Li, Z.; Sun, Z.; Ren, Q.; Zhang, Q.; Li, H.; Li, J. J. Org. Chem. 2020, 85, 4365. doi: 10.1021/acs.joc.0c00050
[29]	(a) Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981. doi: 10.1021/cr2002646 pmid: 30300843
	(b) Montchamp, J.-L. Acc. Chem. Res. 2014, 47, 77. doi: 10.1021/ar400071v pmid: 30300843
	(c) Mady, M. F.; Kelland, M. A. Energy Fuels 2017, 31, 4603. doi: 10.1021/acs.energyfuels.7b00708 pmid: 30300843
	(d) Ntatsopoulos, V.; Macegoniuk, K.; Mucha, A.; Vassiliou, S.; Berlicki, Ł. Eur. J. Med. Chem. 2018, 159, 307. doi: S0223-5234(18)30859-6 pmid: 30300843
[30]	Li, K.-J.; Jiang, Y.-Y.; Xu, K.; Zeng, C.-C.; Sun, B.-G. Green Chem. 2019, 21, 4412. doi: 10.1039/C9GC01474H

电化学条件下喹喔啉-2(1H)-酮C(3)—H功能化的研究进展

Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 27

References 30

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[2]	Junying Zhang, Xiaojing Zhao, Ganpeng Li, Yonghui He. Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1815-1823.
[3]	Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He. Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1416-1434.
[4]	Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei. Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 756-762.
[5]	Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing. Synthesis of Nitrile via Electrochemical Appel Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2229-2235.
[6]	Xin Sun, Chaofan Qu, Chaorui Ma, Xiaowei Zhao, Guobi Chai, Zhiyong Jiang. Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1396-1406.
[7]	Zhengjiang Fu, Zhenjiang Yang, Li Sun, Jian Yin, Xuezheng Yi, Hu Cai, Aiwen Lei. Electrochemical Synthesis of Aryl Sulfonates from Sodium Sulfinates and Phenols under Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 600-606.
[8]	Xiaolong Guo, Yuxian Wang, Zhiqiang Zhao, Qing Wang, Jian Zuo, Luyao Wang. Electrochemical Oxidative C—H Trifluoromethylation of Quinoxalin-2(1H)-ones and the Performance Evaluation via Electro-descriptors [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 641-649.
[9]	Mengqi Zhang, Guangming Nan, Xiaohui Zhao, Wei Wei. Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4315-4322.
[10]	Hongxia Li, Peng Chen, Zhilin Wu, Yuhan Lu, Junmei Peng, Jingyang Chen, Weimin He. Electrochemical Oxidative Cross-Dehydrogenative Coupling of Five-Membered Aromatic Heterocycles with NH₄SCN [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3398-3404.
[11]	Xiang Liu, Wen Li, Canzhan Zhuang, Hua Cao. Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3459-3481.
[12]	Rongnan Yi, Dongxian Liu, Jiangnan He, Mingming Zhao, Xinhua Xu. Ammonium Persulfate Promotes Trifluoromethylation of Quinoxalin-2(1H)-ones [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3285-3291.
[13]	Zhiheng Zhao, Ming Li, Yaqin Zhou, Yonghui He, Lizhu Zhang, Ganpeng Li, Lijun Gu. Synthesis of 1,2,4-Triazoles via the Electrochemical Oxidative [3+2] Annulation [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2476-2484.
[14]	Yaqin Zhou, Zhiheng Zhao, Liang Zeng, Ming Li, Yonghui He, Lijun Gu. Recent Advance in Organic Electrochemical Synthesis of Nitrogenous Heterocyclic Compounds Involving Haloids as Mediators [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1072-1080.
[15]	Wenyi Li, Yinheng Tang, Wentao Ouyang, Yuhan Lu, Jinyang Chen, Weimin He. Electrochemical Selenylation of N-Unprotected Anilines for Consturcing 4-(Organylselanyl)anilines [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4766-4772.