研究论文

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 ,
  • 李国锋 ,
  • 孙凯 ,
  • 张冰
展开
  • 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

  网络出版日期: 2020-03-06

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 ,
  • Li Guofeng ,
  • Sun Kai ,
  • Zhang Bing
Expand
  • 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 date: 2020-02-27

  Revised date: 2020-02-29

  Online 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).

摘要

发展了一种过氧化物诱导的2-芳基苯并咪唑衍生物,在温和条件下经历自由基环化反应,一步合成了系列骨架多样性的苯并咪唑并异喹啉酮化合物的新方法.该反应具有底物范围宽泛、官能团兼容性好、步骤经济等特点.机理研究表明该反应经历了碳中心自由基历程.

本文引用格式

王薪 , 李国锋 , 孙凯 , 张冰 . 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[J]. 有机化学, 2020 , 40(4) : 913 -921 . DOI: 10.6023/cjoc202002040

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.

参考文献

[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.)
文章导航

/

〈 〉