Recent Advances on the Catalytic Functionalization of Quinoxalin- 2(1H)-ones via C-H Bond Activation

doi:10.6023/cjoc201904025

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1529-1547.DOI: 10.6023/cjoc201904025 Previous Articles Next Articles

Special Issue: 金属有机化学；碳氢活化合辑2018-2019

Reviews

通过C-H键活化喹喔啉-2(1H)-酮催化功能化的研究进展

毛璞^a, 朱军亮^a, 袁金伟^a, 杨亮茹^a, 肖咏梅^a, 张长森^b

a 河南工业大学化学化工学院河南省天然药物化学院士工作站郑州 450001;
b 郑州大学化学与分子工程学院郑州 450001

收稿日期:2019-04-10 修回日期:2019-04-24 发布日期:2019-05-06
通讯作者: 袁金伟 E-mail:yuanjinweigs@126.com
基金资助:
河南省科技厅自然科学基金（Nos.172102210225，182102310675）、河南省教育厅自然科学基金（No.17A150005）、郑州市创新团基金（No.131PCXTD605）和河南工业大学青年骨干教师基金（No.2016003）资助项目.

Recent Advances on the Catalytic Functionalization of Quinoxalin- 2(1H)-ones via C-H Bond Activation

Mao Pu^a, Zhu Junliang^a, Yuan Jinwei^a, Yang Liangru^a, Xiao Yongmei^a, Zhang Changsen^b

a Academician Workstation for Natural Medicinal Chemistry of Henan Province, School of Chemistry & Chemical Engineering, Henan Univeristy of Technology, Zhengzhou 450001;
b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received:2019-04-10 Revised:2019-04-24 Published:2019-05-06
Contact: 10.6023/cjoc201904025 E-mail:yuanjinweigs@126.com
Supported by:
Project supported by the Department of Henan Province Natural Science and Technology Foundation (Nos. 172102210225 and 182102310675), the Natural Science Foundation in Henan Province Department of Education (No. 17A150005), the Program for Innovative Research Team from Zhengzhou (No. 131PCXTD605), and the Project of Youth Backbone Teachers of Henan University of Technology (No. 2016003).

Quinoxalin-2(1H)-ones are very important N-heterocyclic moieties found in natural products and pharmaceuticals, and exhibit an amazingly wide spectrum of biological properties. Numerous efforts have been devoted to the development of efficient approaches for the C-H bond activation and functionalization of quinoxalin-2(1H)-ones in recent years, including alkylation, benzylation, acylation, arylation,amination, amidation, phosphonation, and fluoroalkylation. The recent advances in this area are summarized and their reaction mechanisms are discussed.

Key words: quinoxalin-2(1H)-one, C-H bond activation, functionalization, transition-metal catalyst

Cite this article

Mao Pu, Zhu Junliang, Yuan Jinwei, Yang Liangru, Xiao Yongmei, Zhang Changsen. Recent Advances on the Catalytic Functionalization of Quinoxalin- 2(1H)-ones via C-H Bond Activation[J]. Chin. J. Org. Chem., 2019, 39(6): 1529-1547.

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References

[1] (a) Shi, L.; Zhou, H.; Wu, J.; Li, X. Mini-Rev. Org. Chem. 2015, 12, 96.
(b) Pereira, J. A.; Pessoa, A. M.; Cordeiro, M. N. D. S.; Fernandes, R.; Prudêncio, C.; Noronha, J. P.; Vieira, M. Eur. J. Med. Chem. 2015, 97, 664.
(c) Willardsen, J. A.; Dudley, D. A.; Cody, W. L.; Chi, L.; McClanahan, T. B.; Mertz, T. E.; Potoczak, R. E.; Narasimhan, L. S.; Holland, D. R.; Rapundalo, S. T.; Edmunds, J. J. J. Med. Chem. 2004, 47, 4089.
[2] (a) Wagle, S.; Adhikari, A. V.; Kumari, N. S. Ind. J. Chem. 2008, 47, 439.
(b) Badran, M. M.; Abouzid, K. A. M.; Hussein, M. H. M. Arch. Pharm. Res. 2003, 26, 107.
(c) TenBrink, R. E.; Im, W. B.; Sethy, V. H.; Tang, A. H.; Carter, D. B. J. Med. Chem. 1994, 37, 758.
[3] (a) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
(b) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550.
[4] (a) Chen, X.; Li, J. J.; Hao, X. S.; Goodhu, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 78.
(b) Chen, X.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 12634.
(c) Zhang, Y.; Feng, J.; Li, C. J. J. Am. Chem. Soc. 2008, 130, 2900.
(d) He, T.; Yu, L.; Zhang, L.; Wang, L.; Wang, M. Org. Lett. 2011, 13, 5016.
(e) Guo, S.; Kumar, P. S.; Yang, M. Adv. Synth. Catal. 2017, 359, 2.
(f) Jafarpour, F.; Darvishmolla, M. Org. Biomol. Chem. 2018, 16, 3396.
[5] Nikam, S. S.; Sahasrabudhe, A. D.; Shastri, R. K.; Ramanathan, S. Synthesis 1983, 145.
[6] (a) Velaparthi, S.; Brunsteiner, M.; Uddin, R.; Wan, B.; Franzblau, S. G.; Petukhov, P. A. J. Med. Chem. 2008, 51, 1999.
(b) Wang, A.; Li, X.; Chen, C.; Wu, H.; Qi, Z.; Hu, C.; Yu, K.; Wu, J.; Liu, J.; Liu, X.; Hu, Z.; Wang, W.; Wang, W.; Wang, W.; Wang, L.; Wang, B.; Liu, Q.; Li, L.; Ge, J.; Ren, T.; Zhang, S.; Xia, R.; Liu, J.; Liu, Q. J. Med. Chem. 2017, 60, 8407.
(c) Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207.
[7] (a) Fujiwara, T.; O'Hagan, D. J. Fluorine Chem. 2014, 167, 16.
(b) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
(c) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
(d) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.
[8] Liu, S.; Huang, Y.; Qing, F. L.; Xu, X. H. Org. Lett. 2018, 20, 5497.
[9] (a) Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597.
(b) Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. J. Med. Chem. 2010, 53, 7902.
(c) May, E. L.; Jacobson, A. E.; Mattson, M. V.; Traynor, J. R.; Woods, J. H.; Harris, L. S.; Bowman, E. R.; Aceto, M. D. J. Med. Chem. 2000, 43, 5030.
(d) Fleming, F. F.; Zhang, Z. Y. Tetrahedron 2005, 61, 747.
(e) López, R.; Palomo, C. Angew. Chem., Int. Ed. 2015, 54, 13170.
[10] Yang, L.; Gao, P.; Duan, X. H.; Gu, Y. R.; Guo, L. N. Org. Lett. 2018, 20, 1034.
[11] (a) Martinez, C.; Alvarez R.; Aurrecoechea, J. M. Org. Lett. 2009, 11, 1083.
(b) Ackermann, L.; Lygin A. V.; Hofmann, N. Angew Chem., Int. Ed. 2011, 123, 6503.
(c) Zhou, B.; Yang Y.; Li, Y. Chem. Commun. 2012, 48, 5163.
(d) Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew Chem., Int. Ed. 2009, 48, 5094.
[12] Yuan, J.; Fu, J.; Yin, J.; Dong, Z.; Xiao, Y.; Mao, P.; Qu, L. Org. Chem. Front. 2018, 5, 2820.
[13] (a) Zou, Y. Q.; Chen, J. R.; Liu, X. P.; Lu, L. Q.; Davis, R. L.; Jørgensen, K. A.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 784.
(b) Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97.
(c) Zhang, L.; Yi, H.; Wang, J.; Lei, A. Green Chem. 2016, 18, 5122.
(d) Shi, Q.; Li, P.; Zhu, X.; Wang, L. Green Chem. 2016, 18, 4916.
(e) Li, X.; Fang, X.; Zhuang, S.; Liu, P.; Sun, P. Org. Lett. 2017, 19, 3580.
[14] Wei, W.; Wang, L.; Yue, H.; Bao, P.; Liu, W.; Hu, C.; Yang, D.; Wang, H. ACS Sustainable Chem. Eng. 2018, 6, 17252.
[15] (a) Zhou, W.; Qian, P.; Zhao, J.; Fang, H.; Han, J.; Pan, Y. Org. Lett. 2015, 17, 1160.
(b) Mallat, T.; Baiker, A. Chem. Rev. 2004, 104, 3037.
(c) Zhang, S. Y.; Tu, Y. Q.; Fan, C. A.; Zhang, F. M.; Shi, L. Angew. Chem., Int. Ed. 2009, 48, 8761.
(d) Hu, W.; Sun, S.; Cheng, J. J. Org. Chem. 2016, 81, 4399.
(e) Meng, Y.; Guo, L. N.; Wang, H.; Duan, X. H. Chem. Commun. 2013, 49, 7540.
[16] Fu, J.; Yuan, J.; Zhang, Y.; Xiao, Y.; Mao, P.; Diao, X.; Qu, L Org. Chem. Front. 2018, 5, 3382.
[17] (a) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251.
(b) Yamada, K.; Tomioka, K. Chem. Rev. 2008, 108, 2874.
(c) Slater, K.; Friestad, G. K. J. Org. Chem. 2015, 80, 6432.
[18] Zheng, D.; Studer, A. Org. Lett. 2019, 21, 325.
[19] (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(c) Nie, J.; Guo, H. C.; Cahard, D.; Ma, J. A. Chem. Rev. 2011, 111, 455.
[20] Wang, L.; Zhang, Y.; Li, F.; Hao, X.; Zhang, H. Y.; Zhao, J. Adv. Synth. Catal. 2018, 360, 3969.
[21] (a) Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626.
(b) Xu, Y.; Aoki, J.; Shimizu, K.; Umezu-Goto, M.; Hama, K.; Takanezawa, Y.; Yu, S.; Mills, G. B.; Arai, H.; Qian, L.; Prestwich, G. D. J. Med. Chem. 2005, 48, 3319.
(c) Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560.
[22] Hong, G.; Yuan, J.; Fu, J.; Pan, G.; Pan, Z.; Wang, Z.; Yang, L.; Xiao, Y.; Mao, P.; Zhang, X. Org. Chem. Front. 2019, 6, 1173.
[23] (a) Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594.
(b) Wu, B.; Yang, Y.; Qin, X.; Zhang, S.; Jing, C.; Zhu, C.; Ma, B. ChemMedChem 2013, 8, 1913.
(c) 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.
(d) Kobayashi, Y.; Suzuki, Y.; Ogata, T.; Kimachi, T.; Takemoto, Y. Tetrahedron Lett. 2014, 55, 3299.
[24] Hu, L.; Yuan, J.; Fu, J.; Zhang, T.; Gao, L.; Xiao, Y.; Mao, P.; Qu, L. Eur. J. Org. Chem. 2018, 2018, 4113.
[25] (a) Piras, S.; Loriga, M.; Carta, A.; Paglietti, G.; Costi, M. P.; Ferrari, S. J. Heterocycl. Chem. 2006, 43, 541.
(b) Kucybala, Z.; Paczkowski, J. J. Photochem. Photobiol. A 1999, 128, 135.
(c) Honda, H.; Shibusawa, Y.; Taniguchi, J.; Matsuda, H.; Kondod, M.; Kumasaka, K.; Miwa, T.; Notoya, Y.; Shindo, H. Vascul. Pharmacol. 2005, 42, 163.
(d) Azuma, K.; Suzuki, S.; Uchiyama, S.; Kajiro, T.; Santa, T.; Imai, K. Photochem. Photobiol. Sci. 2003, 2, 443.
[26] (a) Wei, Y.; Hu, P.; Zhang, M.; Su, W. Chem. Rev. 2017, 117, 8864.
(b) Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030.
[27] Zeng, X.; Liu, C.; Wang, X.; Zhang, J.; Wang, X.; Hu, Y. Org. Biomol. Chem. 2017, 15, 8929.
[28] (a) Chen, J.; Wan, M.; Hua, J.; Sun, Y.; Lv, Z.; Li, W.; Liu, L. Org. Biomol. Chem. 2015, 13, 11561.
(b) Chen, X.; Cui, X.; Wu, Y. Org. Lett. 2016, 18, 2411.
(c) Liu, J. Q.; Shen, X. Y.; Liu, Z. H.; Wang, X. S. Org. Biomol. Chem. 2017, 15, 6314.
(d) Jafarpour, F.; Abbasnia, M. J. Org. Chem. 2016, 81, 11982.
[29] Yuan, J. W.; Fu, J. H.; Liu, S. N.; Xiao, Y. M.; Mao, P.; Qu, L. B. Org. Biomol. Chem. 2018, 16, 3203.
[30] (a) Gao, Y.; Lu, W.; Liu, P.; Sun, P.; J. Org. Chem. 2016, 81, 2482.
(b) Li, X.; Fang, X.; Zhuang, S.; Liu, P.; Sun, P. Org. Lett. 2017, 19, 3580.
[31] Xie, L. Y.; Peng, S.; Fan, T. G.; Liu, Y. F.; Sun, M.; Jiang, L. L.; Wang, X. X.; Cao, Z.; He, W. M. Sci. China Chem. 2019, 62, 460.
[32] (a) Myers, M. R.; He, W.; Hanney, B.; Setzer, N.; Maguire, M. P.; Zulli, A.; Bilder, G.; Galzcinski, H.; Amin, D.; Needle, S.; Spada, A. P. Bioorg. Med. Chem. Lett. 2003, 13, 3091.
(b) He, W.; Myers, M. R.; Hanney, B.; Spada, A. P.; Bilder, G.; Galzcinski, H.; Amin, D.; Needle, S.; Page, K.; Jayyosi, Z.; Perrone, M. H. Bioorg. Med. Chem. Lett. 2003, 13, 3097.
(c) Aoki, K.; Koseki, J.; Takeda, S.; Aburada, M.; Miyamoto, K. Chem. Pharm. Bull. 2007, 55, 922.
[33] (a) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
(b) Lei, F.; Chen, Y. J.; Sui, Y.; Liu, L.; Wang, D. Synlett 2003, 1160.
[34] Han, Y. Y.; Wu, Z. J.; Zhang, X. M.; Yuan, W. C. Tetrahedron Lett. 2010, 51, 2023.
[35] (a) Hussain, S.; Pareen, 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.
(b) Yin, K.; Zhang, R. Org. Lett. 2017, 19, 1530.
[36] (a) Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97.
(b) Keshari, T.; Yadav, V. K.; Srivastava, V. P.; Yadav, L. D. S. Green Chem. 2014, 16, 3986.
(c) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Soc. Rev. 2016, 45, 2044.
[37] Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189.
[38] Jung, H. I.; Lee, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2018, 39, 1003.
[39] Carrër, A.; Brion, J. D.; Messaoudi, S.; Alami, M. Org. Lett. 2013, 15, 5606.
[40] (a) Demir, A. S.; Reis, O.; Emrullahoglu, M. J. Org. Chem. 2003, 68, 578.
(b) Dickschat, A.; Studer, A. Org. Lett. 2010, 12, 3972.
(c) Yan, G. B.; Yang, M. H.; Wu, X. M. Org. Biomol. Chem. 2013, 11, 7999.
(d) Yuan, J. W.; Yang, L. R.; Yin, Q. Y.; Mao, P.; Qu, L. B. RSC Adv. 2016, 6, 35936.
[41] Ramesh, B.; Reddy, C. R.; Kumar, G. G.; Reddy, B. S. Tetrahedron Lett. 2018, 59, 628.
[42] (a) Surry, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
(b) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
(c) Callonnec, F. L.; Fouquet, E.; Felpin, F. X. Org. Lett. 2011, 13, 2646.
(d) Honraedt, A.; Callonnec, F. L.; Grognec, E. L.; Fernandez, V.; Felpin, F. X. J. Org. Chem. 2013, 78, 4604.
[43] Yuan, J.; Liu, S.; Qu, L. Adv. Synth. Catal. 2017, 359, 4197.
[44] Yin, K.; Zhang, R. Synlett 2018, 29, 597.
[45] (a) Yang, Y.; Li, R.; Zhao, Y.; Zhao, D.; Shi, Z. J. Am. Chem. Soc. 2016, 138, 8734.
(b) Liu, C.; Wang, Q. Org. Lett. 2016, 18, 5118.
(c) Zhou, B.; Hou, W.; Yang, Y.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 1322.
(d) Li, P.; Cheng, G.; Zhang, H.; Xu, X.; Gao, J.; Cui, X. J. Org. Chem. 2014, 79, 8156.
[46] Yin, K.; Zhang, R. Org. Lett. 2017, 19, 1530.
[47] (a) Hofmann, J.; Jasch, H.; Heinrich, M. R. J. Org. Chem. 2014, 79, 2314.
(b) Jiang, T.; Chen, S. Y.; Zhuang, H.; Zeng, R. S.; Zou, J. P. Tetrahedron Lett. 2014, 55, 4549.
[48] (a) Cui, J.; Jia, Q.; Feng, R.; Liu, S.; He, T.; Zhang, C. Org. Lett. 2014, 16, 1442.
(b) Shen, H.; Li, J.; Liu, Q.; Pan, J.; Huang, R.; Xiong, Y. J. Org. Chem. 2015, 80, 7212.
(c) Zheng, C.; Wang, Y.; Fan, R. Org. Lett. 2015, 17, 916.
[49] Paul, S.; Ha, J. H.; Park, G. E.; Lee, Y. R. Adv. Synth. Catal. 2017, 359, 1515.
[50] Paul, S.; Khanal, H. D.; Clinton, C. D.; Kim, S. H.; Lee, Y. R. Org. Chem. Front. 2019, 6, 231.
[51] (a) Ghadage, R. V.; Shirote, P. J. J. Chem. Pharm. Res. 2011, 3, 260.
(b) Galal, S. A.; Abdelsamie, A. S.; Tokuda, H.; Suzuki, N.; Lida, A.; ElHefnawi, M. M.; Ramadan, R. A.; Atta, M. H. E.; EI Diwani, H. I. Eur. J. Med. Chem. 2011, 46, 327.
(c) Rangisetty, J. B.; Gupta, C. N. V. H. B.; Prasad, A. L.; Srinivas, P.; Sridhar, N.; Parimoo, P.; Veeranjaneyulu, A. J. Pharm. Pharmacol. 2001, 53, 1409.
[52] Gulevskaya, A. V.; Burov, O. N.; Pozharskii, A. F.; Kletskii, M. E.; Korbukova, I. N. Tetrahedron 2008, 64, 696.
[53] Li, Y.; Gao, M.; Wang, L.; Cui, X. Org. Biomol. Chem. 2016, 14, 8428.
[54] Gupta, A.; Deshmukh, M. S.; Jain, N. J. Org. Chem. 2017, 82, 4784.
[55] Wei, W.; Wang, L.; Bao, P.; Shao, Y.; Yue, H.; Yang, D.; Yang, X.; Zhao, X.; Wang, H. Org. Lett. 2018, 20, 7125.
[56] (a) Jiang, Y. Y.; Xu, K.; Zeng, C. C. Chem. Rev. 2018, 118, 4485.
(b) Yoshida, J. I.; Shimizu, A.; Hayashi, R. Chem. Rev. 2018, 118, 4702.
(c) Wu, Z. J.; Li, S. R.; Long, H.; Xu, H. Z. Chem. Commun. 2018, 54, 4601.
(d) Shrestha, A.; Lee, M.; Duan, A. L.; Sanford, M. S. Org. Lett. 2018, 20, 204.
[57] (a) Xu, F.; Li, Y. J.; Huang, C.; Xu, H. C. ACS Catal. 2018, 8, 3820.
(b) Qian, P.; Su, J. H.; Wang, Y. K.; Bi, M. X.; Zha, Z. G.; Wang, Z. Y. J. Org. Chem. 2017, 82, 6434.
(c) Sauermann, N.; Mei, R. H.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5090.
(d) Gao, X. L.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. W. J. Am. Chem. Soc. 2018, 140, 4195.
[58] Li, K. J.; Xu, K.; Liu, Y. G.; Zeng, C. C.; Sun, B. G. Adv. Synth. Catal. 2019, 361, 1033.
[59] (a) Peng, J.; Xie, Z.; Chen, M.; Wang, J.; Zhu, Q. Org. Lett. 2014, 16, 4702.
(b) Pan, C.; Jin, N.; Zhang, H.; Han, J.; Zhu, C. J. Org. Chem. 2014, 79, 9427.
(c) Zhang, Z.; Kumar, R. K.; Li, G.; Wu, D.; Bi, X. Org. Lett. 2015, 17, 6190.
(d) Xie, Z.; Peng, J.; Zhu, Q. Org. Chem. Front. 2016, 3, 82.
(e) Wu, Z.; Xu, P.; Zhou, N.; Duan, Y.; Zhang, M.; Zhu, C. Chem. Commun. 2017, 53, 1045.
(f) Kong, X.; Lin, L.; Xu, B. Adv. Synth. Catal. 2018, 360, 2801.
[60] Yang, Q.; Yang, Z.; Tan, Y.; Zhao, J.; Sun, Q.; Zhang, H. Y.; Zhang, Y. Adv. Synth. Catal. 2019, 361, 1662.
[61] (a) Dudash Jr, J.; Zhang, Y.; Moore, J. B.; Look, R.; Liang, Y.; Beavers, M. P.; Conway, B. R.; Rybczynski, P. J.; Demarest, K. T. Bioorg. Med. Chem. Lett. 2005, 15, 4790.
(b) Fleischhauer, J.; Beckert, R.; Juttke, Y.; Hornig, D.; Gunther, W.; Birckner, E.; Grummt, U. W.; Goerls, H. Chem. Eur. J. 2009, 15, 12799.
[62] (a) Rach, S. F.; Kühn, F. E. Chem. Rev. 2009, 109, 2061.
(b) Zhang, Y.; Pan, L.; Zou, Y.; Xu, X.; Liu, Q. Chem. Commun. 2014, 50, 14334.
(c) Xu, X.; Zhang, L.; Liu, X.; Pan, L.; Liu, Q. Angew. Chem., Int. Ed. 2013, 52, 9271.
(d) Hu, Z.; Dong, J.; Men, Y.; Lin, Z.; Cai, J.; Xu, X. Angew. Chem., Int. Ed. 2017, 56, 1805.
[63] Yuan, J.; Liu, S.; Xiao, Y.; Mao, P.; Yang, L.; Qu, L. Org. Biomol. Chem. 2019, 17, 876.
[64] Yuan, J.; Zhu, J.; Fu, J.; Yang, L.; Xiao, Y.; Mao, P.; Du, X.; Qu, L. Org. Chem. Front. 2019, 6, 925.
[65] Guo, T.; Wang, C. C.; Fu, X. H.; Liu, Y.; Zhang, P. K. Org. Biomol. Chem. 2019, 17, 3333.
[66] (a) Dang, Q.; Liu, Y.; Cashion, D. K.; Kasibhatla, S. R.; Jiang, T.; Taplin, F.; Jacintho, J. D.; Li, H.; Sun, Z.; Fan, Y.; Re, J. D.; Tian, F.; Li, W.; Gibson, T.; Lemus, R.; Poelje, P. D. J. Med. Chem. 2011, 54, 153.
(b) Roush, R. F.; Nolan, E. M.; Löhr, F.; Walsh, C. T. J. Am. Chem. Soc. 2008, 130, 3603.
(c) Jeon, S. O.; Lee, J. Y. J. Mater. Chem. 2012, 22, 7239.
[67] (a) Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250.
(b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(c) Zhang, X.; Chen, K.; Shi, Z. J. Chem. Sci. 2014, 5, 2146.
[68] Gao, M.; Li, Y.; Xie, L.; Chauvin, R.; Cui, X. Chem. Commun. 2016, 52, 2846.
[69] (a) Meggers, E. Chem. Commun. 2015, 51, 3290.
(b) Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426.
(c) Ravelli, D.; Protri, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
[70] Kim, Y.; Kim, D. Y. Tetrahedron Lett. 2018, 59, 2443.
[71] Nishio, T. J. Org. Chem. 1984, 49, 827.
[72] Carrër, A.; Brion, J. D.; Alami, M.; Messaoudi, S. Adv. Synth. Catal. 2014, 356, 3821.
[73] Yang, Q.; Zhang, Y.; Sun, Q.; Shang, K.; Zhang, H. Y.; Zhao, J. Adv. Synth. Catal. 2018, 360, 4509.

通过C-H键活化喹喔啉-2(1H)-酮催化功能化的研究进展

Recent Advances on the Catalytic Functionalization of Quinoxalin- 2(1H)-ones via C-H Bond Activation

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