ARTICLES

Electrochemistry-Enabled Copper-Catalyzed Oxidation of Benzyl Alcohols for the Preparation of Quinazolinones in Water

  • Mei Wu ,
  • Ling Yu ,
  • Huiqing Hou ,
  • Houzheng Chen ,
  • Qinglong Zhuang ,
  • Sunying Zhou ,
  • Xiaoyan Lin
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  • a Department of Pharmacy, Fujian Medical University, Fuzhou 350004
    b Xingtai University, Xingtai, Hebei 054001
*Corresponding author.E-mail:

Received date: 2020-12-18

  Revised date: 2021-03-03

  Online published: 2021-03-22

Supported by

Natural Science Foundation of Fujian Province(2015MP008); Natural Science Foundation of Fujian Province(2017J01820); and the Fujian Medical University Sailing Foundation(2018QH2021)

Abstract

Quinazolinone is one of the most important nitrogen-containing heterocyclic compound, which is widely found in numerous natural products and synthetic drugs. Quinazolinone derivatives were synthesized by one-pot co-oxidation of benzyl alcohol with CuCl2 and electric current in aqueous phase. The reaction provides an efficient protocol to a series of quinazolinones derivatives in good to high yields. This synthesis process features convenient operation and environmental friendliness, which make it a promising method for the preparation of quinazolinone derivatives insteading of expensive and toxic oxidants with electric current.

Cite this article

Mei Wu , Ling Yu , Huiqing Hou , Houzheng Chen , Qinglong Zhuang , Sunying Zhou , Xiaoyan Lin . Electrochemistry-Enabled Copper-Catalyzed Oxidation of Benzyl Alcohols for the Preparation of Quinazolinones in Water[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2326 -2334 . DOI: 10.6023/cjoc202012028

References

[1]
(a) Kametani, T.; Loc, C. V.; Higa, T.; Koizumi, M.; Ihara, M.; Fukumoto, K. J. J. Am. Chem. Soc. 1977, 99,2306.
[1]
(b) Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Heterocycles 1999, 51,1883.
[2]
(a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103,893.
[2]
(b) Xu, L.; Jiang, Y.; Ma, D. Org. Lett. 2012, 14,1150.
[2]
(c) Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62,9787.
[2]
(d) Witt, A.; Bergman, J. Curr. Org. Chem. 2003, 7,659.
[2]
(e) Khan, I.; Ibrar, A.; Abbas, N.; Saeed, A. Eur. J. Med. Chem. 2014, 76,193.
[3]
(a) Kaur, R.; Manjal, S. K.; Rawal, R. K.; Kumar, K. Bioorg. Med. Chem. 2017, 25,4533.
[3]
(b) Lin, C.-J.; Chang, Y.-L.; Yang, Y.-L.; Chen, Y.-L. Med. Mycol. 2020,DOI: 10.1093/mmy/myaa074.
[4]
(a) Jahng, Y.; Kwon, O. K.; Lee, S. Arch. Pharm. Res. 2012, 35,2199.
[4]
(b) Bowman, W. R.; Elsegood, M. R.; Stein, T.; Weaver, G. W. Org. Biomol. Chem. 2007, 5,103.
[5]
(a) Romero, A. H.; Salazar, J.; Lopez, S. E. Synthesis 2013, 45,2043.
[5]
(b) Hikawa, H.; Ino, Y.; Suzuki, H.; Yokoyama, Y. J. Org. Chem. 2012, 77,7046.
[6]
Larsen, P. J.; Lykkegaard, K.; Larsen, L. K.; Fleckner, J.; Sauerberg, P.; Wassermann, K.; Wulff, E. M. Eur. J. Pharmacol. 2008, 596,173.
[7]
Ionescu-Pioggia, M.; Bird, M.; Orzack, M. H.; Benes, F.; Beake, B.; Cole, J. O. Int. Clin. Psychopharm. 1988, 3,97.
[8]
(a) Wan, Z.-K.; Wacharasindhu, S.; Levins, C. G.; Lin, M.; Tabei, K.; Mansour, T. S. J. Org. Chem. 2007, 72,10194.
[8]
(b) McLaughlin, N. P.; Evans, P.; Pines, M. Bioorg. Med. Chem. 2014, 22,1993.
[8]
(c) Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Chem. Rev. 2011, 111,7157.
[9]
(a) Chen, J.; Natte, K.; Spannenberg, A.; Neumann, H.; Langer, P.; Beller, M.; Wu, X.-F. Angew. Chem. Int. Ed. 2014, 53,7579.
[9]
(b) Chen, J.; Neumann, H.; Bellera, M.; Wu, X.-F. Org. Biomol. Chem. 2014, 12,5835.
[9]
(c) Rather, B. A.; Raj, T.; Reddy, A.; Ishar, M. P. S.; Sivakumar, S.; Paneerselvam, P. Arch. Pharm. Chem. Life Sci. 2010, 343,108.
[9]
(d) Maiden, T. M. M.; Harrity, J. P. A. Org. Biomol. Chem. 2016, 14,8014.
[9]
(e) Rohokale, R. S.; Kshirsagar, U. A. Synthesis 2016, 48,1253.
[9]
(f) Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. Green Chem. 2013, 15,2713.
[9]
(g) He, L.; Li, H.; Chen, J.; Wu, X.-F. RSC Adv. 2014, 4,12065.
[9]
(h) Teng, Q.-H.; Sun, Y.; Yao, Y.; Tang, H.-T.; Li, J.-R.; Pan, Y.-M. ChemElectorChem 2019, 6,3120.
[9]
(i) Yao, Y.; Meng, X.-J.; Teng, Q.-H.; Chen, Y.-Y. Synlett 2020, 31,1795.
[9]
(j) Chen, X.; Xia, F.; Zhao, Y.; Ma, J.; Ma, Y.; Zhang, D.; Yang, L. Chin. J. Chem. 2020, 38,1239.
[9]
(k) Yang, Q.-L.; Wang, X.-Y.; Weng, X.-J.; Yang, X.; Xu, X.-T.; Tong, X.; Fang, P.; Wu, X.-Y.; Mei, T.-S. Acta Chim. Sinica 2019, 77,866(in Chinese).
[9]
(杨启亮, 王向阳, 翁信军, 杨祥, 徐学涛, 童晓峰, 方萍, 伍新燕, 梅天胜, 化学学报, 2019, 77,866.)
[10]
(a) Bie, Z.; Li, G.; Wang, L.; Lv, Y.; Niu, J.; Gao, S. Tetrahedron Lett. 2016, 57,4935.
[10]
(b) Du, Y.; Zhao, K.; Cheng, R.; Guo, T.; Zhang-Negrerie, D. Synthesis 2013, 45,2998.
[10]
(c) Zhan, D.; Li, T.; Zhang, X.; Dai, C.; Wei, H.; Zhang, Y.; Zeng, Q. Synth. Commun. 2013, 43,2493.
[10]
(d) Sharif, M.; Opalach, J.; Langer, P.; Beller, M.; Wu, X.-F. RSC Adv. 2014, 4,8.
[10]
(e) Juvale, K.; Wiese, M. Bioorg. Med. Chem. Lett. 2012, 22,6766.
[10]
(f) Jia, F.-C.; Zhou, Z.-W.; Xu, C.; Wu, Y.-D.; Wu, A.-X. Org. Lett. 2016, 18,2942.
[10]
(g) Shang, Y.-H.; Fan, L.-Y.; Li, X.-X.; Liu, M.-X. Chin. Chem. Lett. 2015, 26,1355.
[10]
(h) Cheng, R.; Guo, T.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Synthesis 2013, 45,2998.
[11]
(a) Zhang, Z.; Wang, M.; Zhang, C.; Zhang, Z.; Lu, J.; Wang, F. Chem. Commun. 2015, 51,9205.
[11]
(b) Zheng, Y.; Bian, M.; Deng, X.-Q.; Wang, S.-B.; Quan, Z.-S. Arch. Pharm. Chem. Life Sci. 2013, 346,119.
[11]
(c) Du, Y.; Zhao, K.; Cheng, R.; Guo, T.; & Zhang-Negrerie, D. Synthesis 2013, 45,2998.
[12]
Bakavoli, M.; Sabzevari, O.; Rahimizadeh, M. Chin. Chem. Lett. 2007, 18,1466.
[13]
(a) Majumdar, B.; Sarma, D.; Jain, S.; Sarma, T. K. Adv. Synth. Catal. 2013, 355,2308.
[13]
(b) Dandia, A.; Sharma, R.; Indora, A.; Parewa, V. ChemistrySelect 2018, 3,8285.
[13]
(c) Sun, J.; Tao, T.; Xu, D.; Cao, H.; Kong, Q.; Wang, X.; Yun, L.; Zhao, J.; Wang, Y.; Pan, Y. Tetrahedron Lett. 2018, 59,2099.
[13]
(d) Hu, Y.; Chen, L.; Li, B. RSC Adv. 2016, 6,65196.
[13]
(e) Oveisi, A. R.; Khorramabadizad, A.; Daliran, S. RSC Adv. 2016, 6,1136.
[13]
(f) Zhao, D.; Zhou, Y.-R.; Shen, Q.; Li, J.-X. RSC Adv. 2014, 4,6486.
[13]
(g) Li, F.; Lu, L.; Liu, P. C. Org. Lett. 2016, 18,2580.
[13]
Ding, G.; Wang, Z.; Yin, Z.; Yue, G. Chin. J. Org. Chem. 2016, 36,43(in Chinese).
[13]
(丁刚, 王泽宇, 殷中琼, 乐贵洲, 有机化学, 2016, 36,43.)
[14]
Zhou, J. G.; Fang, J. J. Org. Chem. 2011, 76,7730.
[15]
Siddiki, S. M. A. H.; Kon, K.; Touchy, A. S.; Shimizua, K. Catal. Sci. Technol. 2014, 4,1716.
[16]
(a) Wu, X.-F.; Oschatz, S.; Block, A.; Spannenberg, A.; Langer, P. Org. Biomol. Chem. 2014, 12,1865.
[16]
(b) Tang, L.; Zhao, X.; Zou, G.; Zhou, Y.; Yang, X. Asian J. Org. Chem. 2016, 5,335.
[17]
Wang, Q.; Lv, M.; Liu, J.; Li, Y.; Cao, H.; Zhang, X.; Xu, Q. ChemSusChem 2019, 12,3043.
[18]
(a) Adeli, Y.; Huang, K.; Liang, Y.; Jiang, Y.; Liu, J.; Song, S.; Zeng, C.-C.; Jiao, N. ACS Catal. 2019, 9,2063.
[18]
(b) Zheng, M.-W.; Yuan, X.; Cui, Y.-S.; Qiu, J.-K.; Li, G.; Guo, K. Org. Lett. 2018, 20,7784.
[18]
(c) Singh, V. K.; Dubey, R.; Upadhyay, A.; Sharma, L. K.; Singh, R. K. P. Tetrahedron Lett. 2017, 58,4227.
[18]
(d) Cardoso, D. S. P.; Šljukić, B.; Santos, D. M. F.; Sequeira, C. A. C. Org. Process Res. Dev. 2017, 21,1213.
[18]
(e) Röse, P.; Emge, S.; König, C. A.; Hilt, G. Adv. Synth. Catal. 2017, 359,1358.
[18]
(f) Huang, P.; Wang, P.; Wang, S.; Tang, S.; Lei, A. Green Chem. 2018, 20,4870.
[18]
(g) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Han, X.-R.; Wu, Y.; Du, K.; Cao, Z.; Lin, Y.-W.; He, W.-M. Org. Lett. 2020, 22,2206.
[18]
(h) Li, L.; Xue, M.; Yan, X.; Liu, W.; Xu, K.; Zhang, S. Org. Biomol. Chem. 2018, 16,4615.
[19]
(a) Shao, X.; Tian, L.; Wang, Y. Eur. J. Org. Chem. 2019, 2019 4089.
[19]
(b) Yu, Y.; Yuan, Y.; Liu, H.; He, M.; Yang, M.; Liu, P.; Yu, B.; Dong, X.; Lei, A. Chem. Commun. 2019, 55,1809.
[19]
(c) Wiebe, A.; Gieshoff, T.; Möhle, S.; Rodrigo, E.; Zirbes, M.; Waldvogel, S. R. Angew. Chem. Int. Ed. 2018, 57,5594.
[19]
(d) Hou, Z.-W.; Mao, Z.-Y.; Melcamu, Y. Y.; Lu, X.; Xu, H.-C. Angew. Chem. Int. Ed. 2018, 57,1636.
[19]
(e) Yang, Z.; Zhang, J.; Hu, L.; Li, A.; Li, L.; Liu, K.; Yang, T.; Zhou, C. J. Org. Chem. 2020, 85,5952.
[19]
(f) Song, T.; Ren, P.; Ma, Z.; Xiao, J.; Yang, Y. ACS Sustainable Chem. Eng. 2020, 8,267.
[20]
Xu, Z.; Zheng, Y.; Wang, Z.; Shao, X.; Tian, L.; Wang, Y. Chem. Commun. 2019, 55,15089.
[21]
(a) Peng, S.; Song, Y.-X.; He, J.-Y.; Tang, S.-S.; Tan, J.-X.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30,2287.
[21]
(b) Peng, S.; Hu, D.; Hu, J.-L.; Lin, Y.-W.; Tang, S.-S.; Tang, H.-S.; He, J.-Y.; Cao, Z.; He, W.-M. Adv. Synth. Catal. 2019, 361,5721.
[21]
(c) Yang, J.; Fu, T.; Long, Y.; Zhou, X. G. Chin. J. Org. Chem. 2017, 37,1111(in Chinese).
[21]
(杨军, 付婷, 龙洋, 周向葛, 有机化学, 2017, 37,1111.)
[21]
(d) Luo, F. H.; Long, Y.; Li, Z. K.; Zhou, X. G. Acta Chim. Sinica 2016, 74,805(in Chinese).
[21]
(罗飞华, 龙洋, 李正凯, 周向葛, 化学学报, 2016, 74,805.)
[21]
(e) Pradhan, T. R.; Park, J. K. Adv. Synth. Catal. 2020, 362,4833.
[22]
(a) Ke, F.; Xu, Y.; Zhu, S.; Lin, X.; Chen, L.; Zhou, S.; Su, H. Green Chem. 2019, 21,4329.
[22]
(b) Ke, F.; Zhang, P.; Xu, Y.; Lin, X.; Lin, J.; Lin, C.; Xu, J. Synlett 2018, 29,2722.
[22]
(c) Ke, F.; Liu, C.; Zhang, P.; Xu, J.; Chen, X. Synth. Commun. 2018, 48,3089.
[23]
(a) Yang, Q.-L.; Wang, X.-Y.; Lu, J.-Y.; Zhang, L.-P.; Fang, P.; Mei, T.-S. J. Am. Chem. Soc. 2018, 140,11487.
[23]
(b) Lin, D.-Z.; Lai, Y.-L.; Huang, J.-M. ChemElectroChem 2019, 6,4188.
[23]
(c) Liu, Z.; Zeng, L.-Y.; Li, C.; Yang, F.; Qiu, F.; Liu, S.; Xi, B. Molecules 2018, 23,2325.
[23]
(d) Kumar, M.; Richa ; Sharma, S.; Bhatt, V.; Kumar, N. Adv. Synth. Catal. 2015, 357,2862.
[23]
(e) Hu, Y.; Li, S.; Li, H.; Li, Y.; Li, J.; Duanmu, C.; Li, B. Org. Chem. Front. 2019, 6,2744.
[23]
(f) Cao, L.; Huo, H.; Zeng, H.; Yu, Y.; Lu, D.; Gong, Y. Adv. Synth. Catal. 2018, 360,4764.
[24]
(a) Chen, X.; Qi, H.; Wu, S.; Liu, L.; Wen, J.; Li, W.; Guo, F.; Bian, Y.; Li, J. Heterocyles 2017, 94,86.
[24]
(b) Parua, S.; Das, S.; Sikari, R.; Sinha, S.; Paul, N. D. J. Org. Chem. 2017, 82,7165.
[24]
(c) Das, S.; Sinha, S.; Samanta, D.; Mondal, R.; Chakraborty, G.; Brandao, P.; Paul, N. D. J. Org. Chem. 2019, 84,10160.
[24]
(d) Rao, K. R.; Mekala, R.; Raghunadh, A.; Meruva, S. B.; Kumar, S. P.; Kalita, D.; Laxminarayana, E.; Prasad, B.; Pal, M. RSC Adv. 2015, 5,61575.
[24]
(e) Duan, C.; Jia, J.; Zhu, R.; Wang, J. J. Heterocycl. Chem. 2012, 49,865.
[24]
(f) Latha, G.; Devarajan, N.; Suresh, P. ChemistrySelect 2020, 5,10041.
[25]
(a) López, S.; Romero, A.; Salazar, J. Synthesis 2013, 45,2043.
[25]
(b) Hudwekar, A. D.; Reddy, G. L.; Verma, P. K.; Gupta, S.; Vishwakarma, R. A.; Sawant, S. D. ChemistrySelect 2017, 2,4963.
[25]
(c) Tian, X.; Song, L.; Li, E.; Wang, Q.; Yu, W.; Chang, J. RSC Adv. 2015, 5,62194.
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