Visible-Light Promoted Preparation of Benzimidazoles by Eosin Y Catalyzed Reaction of Benzonitrile Derivatives in Water

doi:10.6023/cjoc202004016

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2563-2569.DOI: 10.6023/cjoc202004016 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑

水相中可见光催化腈合成苯并咪唑衍生物

林媚^a, 吴凡^a, 刘天惠^a, 陈志涛^a, 许秀枝^a, 柯方^a,b

a 福建医科大学药学院福州 350004;
b 福建省天然药物药理学重点实验室福州 350004

收稿日期:2020-04-11 修回日期:2020-05-09 发布日期:2020-05-28
通讯作者: 林媚, 柯方 E-mail:linmei@fjmu.edu.cn;kefang@163.com
基金资助:
福建省自然科学基金（Nos.2016Y9052，2016Y9053，2017J01820）资助项目.

Visible-Light Promoted Preparation of Benzimidazoles by Eosin Y Catalyzed Reaction of Benzonitrile Derivatives in Water

Lin Mei^a, Wu Fan^a, Liu Tianhui^a, Chen Zhitao^a, Xu Xiuzhi^a, Ke Fang^a,b

a Department of Pharmacy, Fujian Medical University, Fuzhou 350004;
b Fujian Provincial Key Laboratory of Natural Medicine Pharmacolog, Fuzhou 350004

Received:2020-04-11 Revised:2020-05-09 Published:2020-05-28
Supported by:
Project supported by the Natural Science Foundation of Fujian Province (Nos. 2016Y9052, 2016Y9053, 2017J01820).

1. cjoc202004016辅助材料.pdf(3671KB)

Abstract

A novel visible-light-introduced reaction for the construction of benzimidazole derivatives via radical cyclization of o-phenylenediamines with benzonitrile derivatives in water has been developed. The reaction has been achieved in high yield under mild conditions by using Eosin Y as photocatalyst, which is cheap, easy to handle and environmentally friendly. A variety of benzimidazoles were obtained in up to 91% yields. It might provide a promising protocol for the synthesis of benzimidazole derivatives.

Key words: visible-light photoredox catalysis, eosin Y, benzimidazole, catalyst

Cite this article

Lin Mei, Wu Fan, Liu Tianhui, Chen Zhitao, Xu Xiuzhi, Ke Fang. Visible-Light Promoted Preparation of Benzimidazoles by Eosin Y Catalyzed Reaction of Benzonitrile Derivatives in Water[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2563-2569.

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[1] (a) Zhu, G.; Yang, L.; Cui, D. Chin. J. Org. Chem. 2014, 34, 495(in Chinese). (朱观明, 杨柳阳, 崔冬梅, 有机化学, 2014, 34, 495.)
(b) Dhanamjayulu, P.; Boga, R. B.; Mehta, A. Toxicon 2019, 170, 60.
(c) Ghadari, R.; Namazi, H.; Aghazadeh, M. Appl. Organomet. Chem. 2018, 32, 3965.
(d) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
(e) Ziarati, A.; Badiei, A.; Ziarani, G. M.; Eskandarloo, H. Catal. Commun. 2017, 95, 77.
(f) Ashok, D.; Reddy, M. R.; Nagaraju, N.; Dharavath, R.; Ramakrishna, K.; Gundu, S.; Shravani, P.; Sarasija, M. Med. Chem. Res. 2020, 29, 699.
[2] (a) Algul, O.; Kaessler, A.; Apcin, Y.; Yilmaz, A.; Jose, J. Molecules 2008, 13, 736.
(b) Khattab, M.; Galal, S. A.; Ragab, F. A. F.; Diwani, H. I. E. Res. Chem. Intermed. 2013, 39, 2917.
(c) Khalili, S. B.; Sardarian, A. R. Monatsh. Chem. 2012, 143, 841.
(d) Hu, Z.; Zhao, T.; Wang, M.; Wu, J.; Yu, W.; Chang, J. J. Org. Chem. 2017, 82, 3152.
(e) Wang, S.; Guan, L.; Zang, J.; Xing, K.; Zhang, J.; Liu, D.; Zhao, L. Molecules 2019, 24, 1198.
[3] (a) Khosravi, K.; Kazemi, S. Chin. Chem. Lett. 2012, 23, 61.
(b) Zhang, C.; Zhang, L.-R.; Jiao, N. Green Chem. 2012, 14, 3273.
(c) Shelkar, R.; Sarode, S.; Nagarkar, J. Tetrahedron Lett. 2013, 54, 6986.
[4] (a) Rostamizadeh, S.; Amani, A. M.; Aryan, R.; Ghaieni, H. R.; Norouzi, L. Monatsh. Chem. 2009, 140, 547.
(b) Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 120, 1958.
(c) Martins, G. M.; Puccinelli, T.; Gariani, R. A.; Xavier, F. R.; Silveira, C. C.; Mendes, S. R. Tetrahedron Lett. 2017, 58, 1969.
(d) Nale, D. B.; Bhanage, B. M. Synlett 2015, 26, 2835.
(e) De Luca, L.; Porcheddu, A. Eur. J. Org. Chem. 2011, 5791.
[5] (a) Diao, X.; Wang, Y.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 7974.
(b) Xiao, Q.; Wang, W.-H.; Liu, G.; Meng, F.-K.; Chen, J.-H.; Yang, Z.; Shi, Z.-J. Chem.-Eur. J. 2009, 15, 7292.
(c) Deng, X.; Mani, N. S. Eur. J. Org. Chem. 2010, 2010, 680.
(d) Wray, B. C.; Stambuli, J. P. Org. Lett. 2010, 12, 4576.
(e) Bhagat, S. B.; Ghodse, S. M.; Telvekar, V. N. J. Chem. Sci. 2018, 130, 10.
[6] Qu, Y.; Pan, L.; Wu, Z.; Zhou, X. Tetrahedron 2013, 69, 1717.
[7] Xiang, S.-K.; Zhang, D.-X.; Hu, H.; Shi, J.-L.; Guo, L.-G.; Feng, C.; Wang, B.-Q.; Zhao, K.-Q.; Hu, P.; Yang, H.; Yu, W.-H. Adv. Synth. Catal. 2013, 355, 1495.
[8] (a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
(b) Wu, L.; Wang, L.; Chen, P.; Guo, Y.-L.; Liu, G. Adv. Synth. Catal. 2020, 362, 2189.
(c) Niknam, E.; Panahi, F.; Khalafi-Nezhad, A. Eur. J. Org. Chem. 2020, 2020, 2699.
[9] (a)Yu, J.; Xia, Y.; Lu, M. Appl. Organomet. Chem. 2014, 28, 764.
(b) Cao, Z.; Zhu, Q.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2132
[10] Fujishima, A.; Honda, K. Nature (London) 1972, 238, 37.
[11] (a) Zeng, F.-L.; Sun, K.; Chen, X.-L.; Yuan, X.-Y.; He, S.-Q.; Liu, Y.; Peng, Y.-Y.; Qu, L.-B.; Lv, Q.-Y.; Yu, B. Adv. Synth. Catal. 2019, 361, 5176.
(b) Samanta, S.; Khilari, S.; Srivastava, R. ACS Appl. Nano Mater. 2018, 1, 426.
(c) Li, Z.; Song, H.; Guo, R.; Zuo, M.; Hou, C.; Sun, S.; He, X.; Sun, Z.; Chu, W. Green Chem. 2019, 21, 3602.
(d) Chen, D.; Liu, J.; Zhang, X.; Jiang, H.; Li, J. Chin. J. Org. Chem. 2019, 39, 3353(in Chinese). (陈丹, 刘剑沉, 张馨元, 蒋合众, 李加洪, 有机化学, 2019, 39, 3353.)
(e) 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.
(f) Xie, L.-Y.; Fang, T.-G.; Tan, J.-X.; Zhang, B.; Cao, Z.; Yang, L.-H.; He, W.-M. Green Chem. 2019, 21, 3858.
(g) 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
[12] (a) Li, L.; Huang, M.; Liu, C.; Xiao, J. C.; Chen, Q. Y.; Guo, Y.; Zhao, Z. G. Org. Lett. 2015, 17, 4714.
(b) Zhang, M.; Ruzi, R.; Li, N.; Xie, J.; Zhu, C. Org. Chem. Front. 2018, 5, 749.
(c) Hou, H.; Zhu, S.; Pan, F.; Rueping, M. Org. Lett. 2014, 16, 2872.
[13] Jana, S.; Verma, A.; Kadu, R.; Kumar, S. Chem. Sci. 2017, 8, 6633.
[14] (a) Ke, F.; Xu, Y.; Zhu, S.; Lin, X.; Lin, C.; Zhou, S.; Su, H. Green Chem. 2019, 21, 4329.
(b) Ke, F.; Liu, C.; Zhang, P.; Xu, J.; Chen, X. Synth. Commun. 2018, 48, 3089.
[15] (a) Tian, W.; Xu, S.; Liang, Z.; Sun, D.; Zhang, R. Chin. J. Org. Chem. 2016, 36, 2121(in Chinese). (田文艳, 徐松, 梁中卫, 孙德立, 张荣华, 有机化学, 2014, 36, 2121.)
(b) Jiang, W.-J.; Song, Y.-T.; Wei, X.-J.; Xu, Y.; Lu, J.; Jiang, B.; Hao, W.-J. Chin. J. Org. Chem. 2019, 39, 1095(in Chinese). (蒋文婕, 宋雅婷, 韦晓静, 徐义, 陆娟, 姜波, 郝文娟, 有机化学, 2019, 39, 1095.)
(c) Yue, H.-L.; Bao, P.-L.; Wang, L.-L.; Lü, X.-X.; Yang, D.-S.; Wang, Y.; Wei, W. Chin. J. Org. Chem. 2019, 39, 463(in Chinese). (岳会兰, 鲍鹏丽, 王雷雷, 吕晓霞, 杨道山, 王桦, 魏伟, 有机化学, 2019, 39, 463.)
(d) 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.
[16] (a) Chen, C.; Chen, C.; Li, B.; Tao, J.; Peng, J. Molecules 2012, 17, 12506.
(b) Rahim, G.; Namazi, H.; Aghazadeh, M. Appl. Organomet. Chem. 2018, 32, e3965.
(c) Ghosh, P.; Subba, R. Tetrahedron Lett. 2015, 56, 2691.
(d) Qiu, D.; Wei, H.; Zhou, L.; Zeng, Q. Appl. Organomet. Chem. 2014, 28, 109.
(e) Alapati, M. L. P. R.; Abburi, S. R.; Mukkamala, S. B.; Rao Krishnaji, M. Synth. Commun. 2015, 45, 2436.
(f) Sharghi, H.; Asemani, O.; Khalifeh, R. Synth. Commun. 2008, 38, 1128.
(g) Sun, P.; Hu, Z. J. Heterocycl. Chem. 2006, 43, 773.
(h) Park, S.; Jung, J.; Cho, E. J. Eur. J. Org. Chem. 2014, 4148.
(i) Ravi, O.; Shaikh, A.; Upare, A.; Singarapu, K. K.; Bathula, S. R. J. Org. Chem. 2017, 82, 4422.
(j) Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Heterocycles 2004, 63, 2769.
(k) Panda, S. S.; Jain, S. Synth. Commun. 2011, 41, 729.
(l) Sandera, G.; Isensee, R. W.; Joseph, L. J. Am. Chem. Soc. 1954, 76, 5173.
(m) Wallace, J. M.; Soederberg, B. C. G.; Tamariz, J.; Akhmedov, N. G.; Hurley, M. T. Tetrahedron 2008, 41, 9675.
(n) Murugulla, A. C.; Donthabhakthuni, S.; Takehiko, S. Tetrahedron Lett. 2011, 52, 5575.
(o) Mao, Z.; Wang, C.; Song, X.; Mo, Y. Chin. J. Org. Chem. 2009, 29, 985(in Chinese). (毛郑州, 汪朝阳, 宋秀美, 莫阳青, 有机化学, 2009, 29, 985.)
(p) Kim, Y.; Kumar, M. R.; Park, N.; Heo, Y.; Lee, S. J. Org. Chem. 2011, 76, 9577.
[17] (a) Sharghi, H.; Hosseini Sarvari, M.; Moeini, F. Can. J. Chem. 2008, 86, 1044.
(b) Sharghi, H.; Aberi, M.; Doroodmand, M. M. Adv. Synth. Catal. 2008, 350, 2380.
(c) Chen, Y. X.; Qian, L. F.; Zhang, W.; Han, B. Angew.

水相中可见光催化腈合成苯并咪唑衍生物

Visible-Light Promoted Preparation of Benzimidazoles by Eosin Y Catalyzed Reaction of Benzonitrile Derivatives in Water

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