Peroxide-Induced Radical Relay Carbocyclization towards Polycyclic Benzimidazole[2,1-a]isoquinolines

doi:10.6023/cjoc202002040

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 913-921.DOI: 10.6023/cjoc202002040 Previous Articles Next Articles

过氧化物诱导自由基串联环化合成苯并咪唑并异喹啉酮反应

王薪^a, 李国锋^c, 孙凯^b, 张冰^a,b

a 郑州大学化工学院郑州 455001;
b 安阳师范学院化学化工学院河南安阳 455000;
c 河南师范大学化学化工学院河南新乡 453007

收稿日期:2020-02-27 修回日期:2020-02-29 发布日期:2020-03-06
通讯作者: 孙凯, 张冰 E-mail:sunk468@nenu.edu.cn;zhangb@zzu.edu.cn
基金资助:
国家自然科学基金（No.21801007）和河南省高校科技创新团队（Nos.18IRTSTHN004，18HASTIT006）资助项目.

Peroxide-Induced Radical Relay Carbocyclization towards Polycyclic Benzimidazole[2,1-a]isoquinolines

Wang Xin^a, Li Guofeng^c, Sun Kai^b, Zhang Bing^a,b

a School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001;
b College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000;
c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007

Received:2020-02-27 Revised:2020-02-29 Published:2020-03-06
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21801007) and the Program for Innovative Research Team of Science and Technology in the University of Henan Province (Nos. 18IRTSTHN004, 18HASTIT006).

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Abstract

In this paper, a new peroxide-induced carbon-centered radical relay carbocyclization reaction with 2-arylbenzo-imidazoles is described. This method provides an efficient route to a series of structurally diverse benzimidazole[2,1-a]iso-quinolines under mild conditions in a straightforward manner. The reaction is compatible with a wide substrate scope, excellent functional group tolerance and high step economy. Mechanistic studies suggest that the reaction proceeds through a carbon-centered radical pathway.

Key words: radical, carbocyclization, polycyclic compounds, benzimidazole[2,1-a]isoquinolines

Cite this article

Wang Xin, Li Guofeng, Sun Kai, Zhang Bing. Peroxide-Induced Radical Relay Carbocyclization towards Polycyclic Benzimidazole[2,1-a]isoquinolines[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 913-921.

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[1] (a) Chatgillaloglu, C.; Ingold, K. U.; Nazran, A. S.; Scaiano, J. C. Organometallics 1983, 2, 1332.
(b) Griller, D.; Ingold, K. U. Acc. Chem. Res. 1976, 9, 13.
(c) Katritzky, A. R.; Zerner, M. C.; Karelson, M. M. J. Am. Chem. Soc. 1986, 108, 7213.
(d) Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340.
(e) Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Acc. Chem. Res. 2016, 49, 1924.
(f) Wang, L.-L.; Bao, P.-L.; Liu, W.-W.; Liu, S.-T.; Hu, C.-S.; Yue, H.-L.; Yang, D.-S.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189(in Chinese). (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.)
[2] (a) Wille, U. Chem. Rev. 2013, 113, 813.
(b) Liu, D.; Liu, C.; Lei, A.-W. Chem. Asian J. 2015, 10, 2040.
(c) Xu, J.; Song, Q.-L. Chin. J. Org. Chem. 2016, 36, 1151(in Chinese). (许健, 宋秋玲, 有机化学, 2016, 36, 1151.)
(d) Li, Q.; Li, M.; Shi, S.; Ji, X.; He, C.; Jiang, B.; Hao, W. Chin. J. Org. Chem. 2020, 40, 384(in Chinese). (李庆雪, 李梦伟, 时绍青, 季晓霜, 何春兰, 姜波, 郝文娟, 有机化学, 2020, 40, 384.)
[3] (a) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395.
(b) Guo, X.-X.; Gu, D.-W.; Wu, Z.-X.; Zhang, W.-B. Chem. Rev. 2015, 115, 1622.
(c) Wu, B.; Yoshikai, N. Org. Biomol. Chem. 2016, 14, 5402.
(d) Pan, F.; Shu, C.; Ye, L.-W. Org. Biomol. Chem. 2016, 14, 9456.
(e) Alam, K.; Hong, S. W.; Oh, K. H.; Park, J. K. Angew. Chem., Int. Ed. 2017, 56, 13387.
(f) Xie, W.-L.; Wu, Y.-Q.; Zhang, J.-A.; Mei, Q.-H.; Zhang, Y.-H.; Zhu, N.; Liu, R.-Z.; Zhang, H.-L. Eur. J. Med. Chem. 2018, 145, 35.
(g) Gong, X.; Li, G.; Gan, Z.; Yan, Q.; Dou, X.; Yang, D. Asian J. Org. Chem. 2019, 8, 1472.
(h) Shi, L.; Xu, J.; B, i J.; Zhang, Z.; Liu, T.; Yang, X.; Zhang, G. Chin. J. Org. Chem. 2018, 38, 3016(in Chinese). (李庆雪, 李梦伟, 时绍青, 季晓霜, 何春兰, 姜波, 郝文娟, 有机化学, 2018, 38, 3016.)
(i) Sun, K.; Si, Y.-F.; Chen, X.-L.; Lv, Q.-Y.; Peng, Y.-Y.; Qu, L.-B. Asian J. Org. Chem. 2019, 8, 2042.
[4] (a) Meng, G.; Niu, H.-Y.; Qu, G.-R.; Fossey, J. S.; Li, J.-P.; Guo, H.-M. Chem. Commun. 2012, 48, 9601.
(b) Iaroshenko, V. O.; Ostrovskyi, D.; Miliutina, M.; Maalik, A.; Villinger, A.; Tolmachev, A.; Volochnyuk, D. M.; Langer, P. Adv. Synth. Catal. 2012, 354, 2495.
(c) Sun, X.; Hu, Y.; Nie, S.-Z.; Yan, Y.-Z.; Zhang, X.-J.; Yan, M. Adv. Synth. Catal. 2013, 355, 2179.
(d) Sun, X.; Lv, X.-H.; Ye, L.-M.; Hu, Y.; Chen, Y.-Y.; Zhang, X.-J.; Yan, M. Org. Biomol. Chem. 2015, 13, 7381.
(e) Liu, Y.; Chen, G.-Q.; Tse, C.-W.; Guan, X.; Xu, Z.-J.; Huang, J.-S.; Che, C.-M. Chem. Asian J. 2015, 10, 100.
(f) Nguyen, T. B.; Ermolenkoa, L.; Al-Mourabi, A. Chem. Commun. 2016, 52, 4914.
[5] (a) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.
(b) Wang, Z.; He, W.-M. Chin. J. Org. Chem. 2019, 39, 3594(in Chinese). (王峥, 何卫民, 有机化学, 2019, 39, 3594.)
[6] Mai, S.-Y.; Luo, Y.-X.; Huang, X.-Y.; Shu, Z.-H.; Li, B.-N.; Lan, Y.; Song, Q.-L. Chem. Commun. 2018, 54, 10240.
[7] (a) Sun, K.; Li, S.-J.; Chen, X.-L.; Liu, Y.; Huang, X.-Q.; Wei, D.-H.; Qu, L.-B.; Zhao, Y.-F.; Yu, B. Chem. Commun. 2019, 55, 2861.
(b) 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.
[8] (a) Barreiro, E. J.; Kümmerle, A. E.; Fraga, C. A. M. Chem. Rev. 2011, 111, 5215.
(b) Schönherr, H.; Cernak, T. Angew. Chem., Int. Ed. 2013, 52, 12256.
(c) Yan, G.-B.; Borah, A. J.; Wang, L.-G.; Yang, M.-H. Adv. Synth. Catal. 2015, 357, 1333.
(d) Sun, S.-M.; Fu, J.-M. Bioorg. Med. Chem. Lett. 2018, 28, 3283.
(e) Chen, Y.-T. Chem.-Eur. J. 2019, 25, 3405.
[9] Rust, F. F.; Seubold, F. H.; Vaughan, W. E. J. Am. Chem. Soc. 1948, 70, 3258.
[10] (a) Xia, Q.-Q.; Liu, X.-L.; Zhang, Y.-J.; Chen, C.; Chen, W.-Z. Org. Lett. 2013, 15, 3326.
(b) Xu, Z.-B.; Yan, C.-X.; Liu, Z.-Q. A. Org. Lett. 2014, 16, 5670.
(c) Li, G.; Yang, S.-L.; Lv, B.-J.; Han, Q.-Q.; Ma, X.-X.; Sun, K.; Wang, Z.-Y.; Zhao. F.; Lv, Y.-H.; Wu, H.-K. Org. Biomol. Chem. 2015, 13, 11184.
(d) Bao, Y.-J.; Yan, Y.-Z.; Xu, K.; Su, J.-H.; Zha, Z.-G.; Wang, Z.-Y. J. Org. Chem. 2015, 80, 4736.
(e) Li, Q.; Li, Y.-R.; Hu, W.-P.; Hu, R.-J.; Li, G.-G.; Lu, H.-J. Chem.-Eur. J. 2016, 22, 12286.
(f) Zhang, P.-Z.; Li, J.-A.; Zhang, L.; Shoberu, A.; Zou, J.-P.; Zhang, W. Green Chem. 2017, 19, 919.
[11] (a) Guo, S.-J.; Wang, Q.; Jiang, Y.; Yu, J.-T. J. Org. Chem. 2014, 79, 11285.
(b) Yang, Y.; Bao, Y.-J.; Guan, Q.-Q.; Sun, Q.; Zha, Z.-G.; Wang, Z.-Y. Green Chem. 2017, 19, 112.
(c) Zhu, N.-B.; Zhao, J.-G.; Bao, H.-L. Chem. Sci. 2017, 8, 2081.
[12] (a) Dai, Q.; Yu, J.-T.; Jiang, Y.; Guo, S.-J.; Yang, H.-T.; Cheng, J. Chem. Commun. 2014, 50, 3865.
(b) Dai, Q.; Yu, J.-T.; Feng, X.-M.; Jiang, Y.; Yang, H.-T.; Cheng, J. Adv. Synth. Catal. 2014, 356, 3341.
(c) Tan, F.-L.; Song, R.-J.; Hu, M.; Li, J.-H. Org. Lett. 2016, 18, 3198.
(d) Zhuang, H.; Zeng, R.; Zou, J.-P. Chin. J. Chem. 2016, 34, 368.
(e) Bao, X.; Yokoe, T.; Ha, T. M.; Wang, Q.; Zhu, J.-P. Nat. Commun. 2018, 9, 3725.
(f) Liu, D.; Yu, Y.-Q.; Xia, Z.; Song, Z.-N.; Liao, L.-H.; Tan, Z.; Chen, X. Eur. J. Org. Chem. 2019, 2019, 6930.
[13] (a) Hix, S.; Kadiiska, M. B.; Mason, R. P.; Augusto, O. Chem. Res. Toxicol. 2000, 13, 1056.
(b) Zhu, Y.; Yan, H.; Lu, L.-H.; Liu, D.-F.; Rong, G.-W.; Mao, J.-C. J. Org. Chem. 2013, 78, 9898.
(c) Patel, O. P. S.; Nandwana, N. K.; Sah, A. K.; Kumar, A. Org. Bio-mol. Chem. 2018, 16, 8620.
[14] (a) Sun, K.; Li, Y.; Xiong, T.; Zhang, J.-P.; Zhang, Q. J. Am. Chem. Soc. 2011, 133, 1694.
(b) Sun, K.; Wang, X.; Liu, L.-L.; Sun, J.-J.; Liu, X.; Li, Z.-D.; Zhang, Z.-G.; Zhang, G.-S. ACS Catal. 2015, 5, 7194.
(c) Sun, K.; Li, Y.; Zhang, Q. Sci. China Chem. 2015, 58, 1354.
(d) Wang, X.; Mu, S.-Q.; Sun, T.; Sun, K. Chin. J. Org. Chem. 2019, 39, 2802(in Chinese). (王薪, 穆石强, 孙婷, 孙凯, 有机化学, 2019, 39, 2802.)
(e) Sun, K.; Li, Y.-L.; Feng, R.-R.; Mu, S.-Q.; Wang, X.; Zhang, B. J. Org. Chem. 2020, 85, 1001.
[15] (a) Sun, K.; Wang, X.; Li, D.-H.; Zhu, Z.-H.; Jiang, Y.-Q.; Xiao, B.-B. Chem. Commun. 2014, 50, 12880.
(b) Sun, K.; Lv, Y.-H.; Wang, J.-J.; Sun, J.-J.; Liu, L.-L.; Jia, M.-Y.; Liu, X.; Li, Z.-D.; Wang, X. Org. Lett. 2015, 17, 4408.
(c) Sun, K.; Shi, Z.-D.; Liu, Z.-H.; Luan, B.-X.; Zhu, J.-L.; Xue, Y.-R. Org. Lett. 2018, 20, 6687.
(d) Sun, K.; Wang, S.-N.; Feng, R.-R.; Zhang, Y.-X.; Wang, X.; Zhang, Z.-G.; Zhang, B. Org. Lett. 2019, 21, 2052.
(e) Wang, X.; Li, C.-H.; Zhang, Y.-X.; Zhang, B.; Sun, K. Org. Biomol. Chem. 2019, 17, 8364.
(f) Sun, K.; Li, G.-F.; Li, Y.-Y.; Yu, J.; Zhao, Q.; Zhang, Z.-G.; Zhang, G.-S. Adv. Synth. Catal. 2020, DOI:10.1002/adsc.202000040.
[16] (a) Liu, Y.-Y.; Xiong, J.; Wei, L.; Wan, J.-P. Adv. Synth. Catal. 2020, 362, 877.
(b) Wan, J.-P.; Tu, Z.; Wang, Y.-Y. Chem.-Eur. J. 2019, 25, 6907.
[17] (a) Hu, M.; Fan, J.-H.; Liu, Y.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 9577.
(b) Hu, M.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 608.
(c) Guo, Y.-H.; Xiang, Y.-F.; Wei, L.; Wan, J.-P. Org. Lett. 2018, 20, 3971.
(d) Wan, C.; Song, R.-J.; Li, J.-H. Org. Lett. 2019, 21, 2800.
(e) Wang, L.-L.; Zhang, Y.-L.; Zhang, M.; Bao, P.-L.; Lv, X.-X.; Liu, H.-G.; Zhao, X.-H.; Li, J.-S.; Luo, Z.-D.; Wei, W. Tetrahedron Lett. 2019, 60, 1845.
(f) Li, G.-Q.; Gan, Z.-Y.; Kong, K.-X.; Dou, X.-M.; Yang, D.-S. Adv. Synth. Catal. 2019, 361, 1808.
(g) Xie, L.-Y.; Fang, T.-G.; Tan, J.-X.; Zhang, B.; Cao, Z.; Yang, L.-H.; He, W.-M., Green Chem. 2019, 21, 3858. S.-J.; Jiang, B. Chem. Commun. 2019, 55, 13231.
(i) Guo, T.; Wei, X.-N.; Liu, Y.; Zhang, P.-K.; Zhao, Y.-H. Org. Chem.
(h) Zhang, T.-S.; Zhang, H.-P.; Fu, R.; Wang, J.-Y.; Hao, W.-J.; Tu, Front. 2019, 6, 1414.
(j) Yang, S.-B.; Li, Y.; Zhang, Q. Chin. J. Org. Chem. 2019, 39, 2226(in Chinese). (杨胜彪, 李燕, 张前, 有机化学, 2019, 39, 2226.)

过氧化物诱导自由基串联环化合成苯并咪唑并异喹啉酮反应

Peroxide-Induced Radical Relay Carbocyclization towards Polycyclic Benzimidazole[2,1-a]isoquinolines

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