SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 3: 688 - 693

DOI: https://doi.org/10.6023/cjoc201909021

研究论文

钌(II)-催化偶氮苯与乙醛酸乙酯的环化反应构建3-羧酸酯吲唑

  • 陈训 ,
  • 王颖 ,
  • 王烁今 ,
  • 孔杜林 ,
  • 文丽君 ,
  • 翟锐锐 ,
  • 赵珂 ,
  • 白丽丽 ,
  • 李友宾
展开
  • a 海南医学院 热带转化医学教育部重点实验室 海南省热带药用植物研究开发重点实验室 海口 571199;
    b 海南医学院药学院 海口 571199

收稿日期: 2019-09-15

  修回日期: 2019-11-04

  网络出版日期: 2020-04-02

基金资助

海南省科协青年科技英才学术创新计划（No.QCXM201808）和海南省自然科学基金（No.819QN227）资助项目.

收起

Synthesis of 3-Carboxylate Indazoles via Ru(II)-Catalyzed Annulation of Azobenzenes with Ethyl Glyoxalate

  • Chen Xun ,
  • Wang Ying ,
  • Wang Shuojin ,
  • Kong Dulin ,
  • Wen Lijun ,
  • Zhai Ruirui ,
  • Zhao Ke ,
  • Bai Lili ,
  • Li Youbin
Expand
  • a Key Laboratory of Tropical Translational Medicine of Ministry of Education, Hainan Key Laboratory for Research and Development of Tropical Herbs, Hainan Medical University, Haikou 571199;
    b School of Pharmacy, Hainan Medical University, Haikou 571199

Received date: 2019-09-15

  Revised date: 2019-11-04

  Online published: 2020-04-02

Supported by

Project supported by the Program of Hainan Association for Science and Technology Plans to Youth R&D Innovation (No. QCXM201808) and the Natural Science Foundation of Hainan Province (No. 819QN227).

Fold

摘要

报道了一种简便有效的Ru（II）催化偶氮苯与乙醛酸乙酯的高选择性[4＋1]环化反应，该反应历程涉及C—H键的活化.这种策略能够以中等至良好的产率去高效构建多样性的吲唑骨架结构.同时研究了该反应的动力学同位素效应，实验结果表明C—H键活化可能不属于整个反应历程的决速步骤.

关键词： 钌(II); C—H键活化; 环化反应; 吲唑

本文引用格式

陈训 , 王颖 , 王烁今 , 孔杜林 , 文丽君 , 翟锐锐 , 赵珂 , 白丽丽 , 李友宾 . 钌(II)-催化偶氮苯与乙醛酸乙酯的环化反应构建3-羧酸酯吲唑[J]. 有机化学, 2020 , 40(3) : 688 -693 . DOI: 10.6023/cjoc201909021

Abstract

The Ru(II)-catalyzed regioselective[4+1] cycloaddition of azobenzenes with ethyl glyoxalate through C-H bond activation has been developed. This method provides a facile approach to various 3-carboxylate indazoles in moderate to good yields. Meantime, the kinetic isotope effect was further investigated and the results indicated that the C-H bond-breaking was possibly not involved in the rate-limiting step of this transformation.

Key words： Ru (II); C—H bond activation; cycloaddition; Indazoles

参考文献

[1] (a) De Angelis, M.; Stossi, F.; Carlson, K. A.; Katzenellenbogen, B. S.; Katzenellenbogen, K. A. J. Med. Chem. 2005, 48, 1132.
(b) A Haddadin, M. J.; Conrad, W. E.; Kurth, M. J. Mini-Rev. Med. Chem. 2012, 12, 1293.
(c) Hu, J.-T.; Cheng, Y.-F.; Yang, Y.-Q.; Rao, Y. Chem. Commun. 2011, 47, 10133.
(d) Magano, J.; Waldo, M.; Greene, D.; Nord, E. Org. Process Res. Dev. 2008, 12, 877.
[2] (a) De Lena, M.; Lorusso, V.; Latorre, A.; Fanizza, G.; Gargano, G.; Caporusso, L.; Guida, M.; Catino, A.; Crucitta, E.; Sambiasi, D.; Mazzei, A. Eur. J. Cancer 2001, 37, 364.
(b) Atta-ur-Rahman; Malik, S.; Cun-heng, H.; Clardy, J. Tetrahedron Lett. 1985, 26, 2759.
(c) Halim, R.; Harding, M.; Hufton, R.; Morton, C. J.; Jahangiri, S.; Pool, B. R.; Jeynes, T. P.; Draffan, A. G.; Lilly, M. J.; Frey, B. WO 2012051659, 2011.
(d) Steffan, R. J.; Matelan, E. M. WO 2006050006, 2006.
[3] (a) Luo, G.; Chen, L.; Dubowchik, G. J. Org. Chem. 2006, 71, 5392.
(b) Unsinn, A.; Knochel, P. Chem. Commun. 2012, 48, 2680.
(c) Bunnell, A.; Yang, C.; Petrica, A.; Soth, M. J. Synth. Commun. 2006, 36, 285.
[4] For selected reviews, see: (a) Ackermann, C. Acc. Chem. Res. 2014, 47, 281.
(b) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
(c) Huang, Z.; Lim, H, N.; Mo, F.; Young, M. C.; Dong, G. Chem. Soc. Rev. 2015, 44, 7764.
(d) Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S. A.; Liu, X. Chem. Soc. Rev. 2015, 44, 291.
(e) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
(f) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007.
(g) Zhang, F.; Spring, D. R. Chem. Soc. Rev. 2014, 43, 6906.
(h) Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369.
(i) Chen, X., Bai, L.; Zeng, W. Chin. J. Org. Chem. 2018, 38, 1859(in Chinese). (陈训, 白丽丽, 曾伟, 有机化学, 2018, 38, 1859.)
(j) Zhang, Z.; Butt, N. A.; Zhou, M.; Liu, D.; Zhang, W. Chin. J. Chem. 2018, 36, 443.
(k) Jeong, T.; Han, S. H.; Han, S.; Sharma, S.; Park, J.; Lee, J.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Org. Lett. 2016, 18, 232.
(l) Chen, W.; Yang, W.; Wu, R.; Yang, D. Green Chem. 2018, 20, 2512.
(m) Yang, W.; Chen, Y.; Yao, Y.; Yang, X.; Lin, Q.; Yang, D. J. Org. Chem. 2019, 84, 11080.
(n) Yao, Y.; Yang, W.; Lin, Q.; Yang, W.; Li, H.; Wang, L.; Gu, F.; Yang D. Org. Chem. Front.. 2019, 6, 3360.
[5] Lian, Y.; Bergman, R. G.; Lavis, L. D.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 7122.
[6] (a) Hummel, J. R.; Ellman, J. A. J. Am. Chem. Soc. 2015, 137, 490.
(b) Geng, X.; Wang, C. Org. Lett. 2015, 17, 2434.
[7] (a) T. Gensch, M. N. Hopkinson, F. Glorius, J. Wencel-Delord, Chem. Soc. Rev. 2016, 45, 2900.
(b) Suzuki, C.; Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth. Catal. 2014, 356, 1521.
(c) Itoh, M.; Hashimoto, Y.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2013, 78, 8098.
(d) Suzuki, C.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 3990.
(e) Kong, D.; Lu, G.; Wu, M.; Shi, Z.; Lin, Q. ACS Sustainable chem. Eng. 2017, 5, 3465.
(f) De Sarkar, S.; Liu, W.; Kozhushkov, S. I.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461.
(g) Zhang, Y.; Yang, Z.; Yu, X.; Cheng, X.; Li, W.; Guo, L.; Hai, L.; Guo, L.; Wu, Y. Chin. J. Org. Chem. 2018, 38, 3211(in Chinese). (张勇, 杨中振, 余昕玲, 程旭, 李伟剑, 郭令妹, 海俐, 郭丽, 吴勇, 有机化学, 2018, 38, 3211.)
(h) Xu, W.; Wang, N.; Zhang, M.; Shi, D. Chin. J. Org. Chem. 2019, 39, 1735(in Chinese). (徐文韬, 王宁, 张梦烨, 史达清, 有机化学, 2019, 39, 1735.)
[8] Bai, L.; Wang, Y.; Wang, S.; Kong, D.; Fu, Y.; Peng, D.; Wen, L.; Chen, X. Chin. J. Org. Chem. 2018, 38, 3242(in Chinese). (白丽丽, 王颖, 王烁今, 孔杜林, 付艳, 彭德乾, 文丽君, 陈训, 有机化学, 2018, 38, 3242.)
[9] (a) Li, B.; Xu, H.; Wang, H.; Wang, B. ACS Catal. 2016, 6, 3856.
(b) Huang, X.; Huang, J.; Du, C.; Zhang, X.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52, 12970.
(c) Thirunavukkarasu, V. S.; Raghuvanshi, K.; Ackermann, L. Org. Lett. 2013, 15, 3286.
[10] (a) Chen, X.; Hu, X.; Deng, Y.; Jiang, H.; Zeng, W. Org. Lett. 2016, 18, 4742.
(b) Jeon, B.; Yeon, U.; Son, J. Y.; Lee, P. H. Org. Lett. 2016, 18, 4610.
Options
文章导航

/

〈 〉