Citation: Hai Man, Guo Li-Na, Wang Le, Duan Xin-Hua. Visible Light Promoted Ketoalkylation of Quinoxaline-2(1H)-ones via Oxidative Ring-Opening of Cycloalkanols[J]. Acta Chimica Sinica, ;2019, 77(9): 895-900. doi: 10.6023/A19040155 shu

Visible Light Promoted Ketoalkylation of Quinoxaline-2(1H)-ones via Oxidative Ring-Opening of Cycloalkanols

Hai Man ^a ,
Guo Li-Na ^a ,
Wang Le ^b ,
Duan Xin-Hua ^a,,

a.
Department of Chemistry, School of Science, and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Jiaotong University, Xi'an 710049
b.
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013

Corresponding author: Duan Xin-Hua, duanxh@xjtu.edu.cn
Received Date: 30 April 2019
Available Online: 21 September 2019
Fund Project: Project supported by the Natural Science Foundation in Shaanxi Province (No. 2019JM-299)the Natural Science Foundation in Shaanxi Province 2019JM-299

Figures(4)

Substituted quinoxalin-2(1H)-ones represent an important class of fused heterocyclic compounds which are existing in numerous bioactive natural products, pharmaceuticals, and functional materials. As a result, there are many methods for the synthesis of this heterocyclic compounds over the past several years. In this context, the direct C-H functionalization of quinoxalin-2(1H)-ones have proved to be an effective protocol to diverse heterocycles, such as radical C(3)-H arylation, phosphonation, amination, and acylation of quinoxalin-2(1H)-ones. However, the direct C-H alkylation of quinoxalin-2(1H)-ones is still rare. Because of their importance, it is desirable to introduce alkyl substituents, especially those bearing functional groups, at the 3-position of quinoxalin-2(1H)-ones, which would probably promote their applications in new drug discovery and development. Thus, this article reports a visible light promoted C(3)-ketoalkylation of quinoxaline-2(1H)-ones via oxidative ring-opening of cycloalkanols. At room temperature, the reaction is carried out by using cycloalkanols as the ketoalkylating agent and potassium persulfate as oxidizing agent in a solution of methanol and water (V:V=1:2) for 16 h upon visible light irradiation. A variety of keto-functionalized alkyl moieties with different chain length have been successfully incorporated into the C(3)-position of quinoxalin-2(1H)-ones. Thus, the procedure provides a greener, environmentally friendly and simple method for the synthesis of quinoxalin-2(1H)-one derivatives. A representative procedure for this reaction is given as follows. An oven-dried quartz reaction tube (10 mL) equipped with a magnetic stir bar was charged with K₂S₂O₈ (2.0 equiv., 0.4 mmol), quinoxalin-2(1H)-one 1 (1.0 equiv., 0.2 mmol) and cycloalkanol 2 (1.5 equiv., 0.3 mmol). Then, the tube was evacuated and backfilled with nitrogen (three times). Subsequently, a solution of 1.3 mL of H₂O and 0.7 mL of MeOH were added under nitrogen. Then the reaction tube was sealed and was irradiated under blue light at room temperature for 16 h. After completion of the reaction, ethyl acetate was added to the reaction mixture, and washed with brine (10 mL), dried over Na₂SO₄ and concentrated in vacuo. Purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, V:V=4:1) affords the corresponding product.
- quinoxalin-2(1H)-one,
- cycloalkanol,
- oxidative ring-opening,
- ketoalkylation,
- visible light promoted
1. [1]
  Ries, U. J.; Priepke, H. W. M.; Hauel, N. H.; Handschuh, S.; Mihm, G.; Stassen, J. M.; Wienen, W.; Nar, H. Bioorg. Med. Chem. Lett. 2003, 13, 2297. doi: 10.1016/S0960-894X(03)00443-8
2. [2]
  (a) Carta, A.; Piras, S.; Loriga, G.; Paglietti, G. Mini-Rev. Med. Chem. 2006, 6, 1179. (b) Li, X.; Yang, K.-H.; Li, W.-L.; Xu, W.-F. Drugs Future 2006, 31, 979. (c) Hussain, S.; Parveen, S.; Hao, X.; Zhang, S.-Z.; Wang, W.; Qin, X.-Y.; Yang, Y.-C.; Chen, X.; Zhu, S.-J.; Zhu, C.-J.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383.
3. [3]
  Buratti, W.; Gardini, G. P.; Minisci, F. Tetrahedron 1971, 27, 3655. doi: 10.1016/S0040-4020(01)97776-2
4. [4]
  For review, see: (a) Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, DOI: 10.1002/anie.201900977.For selected examples, see: (b) Huff, C. A.; Cohen, R. D.; Dykstra, K. D.; Streckfuss, E.; DiRocco, D. A.; Krska, S. W. J. Org. Chem. 2016, 81, 6980. (c) Wu, X.-X.; Zhang, H.; Tang, N.-N.; Wu, Z.; Wang, D.-P.; Ji, M.-S.; Xu, Y.; Wang, M.; Zhu, C. Nat. Commun. 2018, 9, 3343. (d) Wu, X.-X.; Wang, M.-Y.; Huan, L.-T.; Wang, D.-P.; Wang, J.-W.; Zhu, C. Angew. Chem., Int. Ed. 2018, 57, 1640.
5. [5]
  (a) Jiao, J.; Murakami, K.; Itami, K. ACS Catal. 2016, 6, 610. (b) Legnani, L.; Cerai, G. P.; Morandi, B. ACS Catal. 2016, 6, 8162. (c) Zhou, Z.; Ma, Z.; Behnke, N. E.; Gao, H.; Kurti, L. J. Am. Chem. Soc. 2017, 139, 115. (d) Wang, P.; Li, G. C.; Jain, P.; Farmer, M. E.; He, J.; Shen, P. X.; Yu, J. Q. J. Am. Chem. Soc. 2016, 138, 14092.
6. [6]
7. [7]
  Gao, M.; Li, Y.; Xie, L.; Chauvin, R.; Cui, X. Org. Biomol. Chem. 2016, 52, 2846.
8. [8]
  Li, Y.; Gao, M.; Wang, L.; Cui, X. Org. Biomol. Chem. 2016, 14, 8428. doi: 10.1039/C6OB01283C
9. [9]
  (a) Yuan, J.-W.; Fu, J.-H.; Liu, S.-N.; Xiao, Y.-M.; Mao, P.; Qu, L.-B. Org. Biomol. Chem. 2018, 16, 3203. (b) 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.
10. [10]
  Hong, G.-F.; Yuan, J.-W.; Fu, J.-H.; Pan, G.-Y.; Wang, Z.-W.; Yang, L.-R.; Xiao, Y.-M.; Mao, P.; Zhang, X.-M. Org. Chem. Front. 2019, 6, 1173. doi: 10.1039/C9QO00105K
11. [11]
  (a) Yuan, J.-W.; Fu, J.-H.; Yin, J.-H.; Dong, Z.-H.; Xiao, Y.-M.; Mao, P.; Qu, L.-B. Org. Chem. Front. 2018, 5, 2820. (b) Fu, J.-H.; Yuan, J.-W.; Zhang, Y.; Xiao, Y.-M.; Mao, P.; Diao, X.-Q.; Qu, L.-B. Org. Chem. Front. 2018, 5, 3382.
12. [12]
  Yang, L.; Gao, P.; Duan, X.-H.; Gu, Y.-R.; Guo, L.-N. Org. Lett. 2018, 20, 1034. doi: 10.1021/acs.orglett.7b03984
13. [13]
  Gu, Y.-R.; Duan, X.-H.; Chen, L.; Ma, Z.-Y.; Gao, P.; Guo, L.-N. Org. Lett. 2019, 21, 917. doi: 10.1021/acs.orglett.8b03865
14. [14]
  (a) Liu, R.; Huang, Z.-H.; Murray, M. G.; Guo, X.-Y.; Liu, G. J. Med. Chem. 2011, 54, 5747. (b) Qin, X.-Y.; Hao, X.; Han, H.; Zhu, S.-J.; Yang, Y.-C.; Wu, B.-B.; Hussain, S.; Parveen, S.; Jing, C.-J.; Ma, B.; Zhu, C.-J. J. Med. Chem. 2015, 58, 1254.
15. [15]
  For review, see: (a) Wu, X.-X.; Zhu, C. Chem. Select. 2017, 2, 10678. For selected examples, see: (b) Ren, R.-G.; Zhao, H.-J.; Huan, L.-T.; Zhu, C. Angew. Chem., Int. Ed. 2015, 54, 12692. (c) Zhao, H.-J.; Fan, X.-F.; Yu, J.-J.; Zhu, C. J. Am. Chem. Soc. 2015, 137, 3490. (d) Wang, S.; Guo, L.-N.; Wang, H.; Duan, X.-H. Org. Lett. 2015, 17, 4798. (e) Jia, K.; Zhang, F.; Huang, H.; Chen, Y. J. Am. Chem. Soc. 2016, 138, 1514. (f) Huan, L.-T.; Zhu, C. Org. Chem. Front. 2016, 3, 1467. (g) Guo, L.-N.; Deng, Z.-Q.; Wu, Y.; Hu, J. RSC Adv. 2016, 6, 27000. (h) Ren, R.-G.; Wu, Z.; Xu, Y.; Zhu, C. Angew. Chem., Int. Ed. 2016, 55, 2866. (i) Nikolaev, A.; Legault, C. Y.; Zhang, M.-H.; Orellana, A. Org. Lett. 2018, 20, 796. (j) Zhao, R.; Yao, Y.; Zhu, D.; Chang, D.-H.; Liu, Y.; Shi, L. Org. Lett. 2018, 20, 1228.
16. [16]
17. [17]
  For selected examples, see: (a) Minisci, F.; Citterio, A.; Giordano, C. Acc. Chem. Res. 1983, 16, 27. (b) Chinchilla, R.; Najera, C.; Yus, M. Chem. Rev. 2004, 104, 2667. (c) Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128. (d) Wei, W.; Wen, J.-W.; Yang, D.-S.; Du, J.; You, J.-M.; Wang, H. Green Chem. 2014, 16, 2988. (e) Li, Y.-M.; Shen, Y.-H.; Chang, K.-J.; Yang, S.-D. Tetrahedron 2014, 70, 1991. (f) Laha, J. K.; Patel, K. V.; Tummalapalli, K. S. S.; Dayal, N. Chem. Commun. 2016, 52, 10245.
18. [18]
  (a) Devan, S.; Shah, B.-A. Chem. Commun. 2016, 52, 1490. (b) Zhang, Y.-Q.; Teuscher, K. B.; Ji, H.-T. Chem. Sci. 2016, 7, 2111. (c) Zhao, Y.-T.; Huang, B.-B.; Yang, C.; Xia, W.-J. Org. Lett. 2016, 18, 3326. (d) Meyer, A. U.; Alexander, W.; K nig, B. Angew. Chem., Int. Ed. 2017, 56, 409.
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