研究论文

钌(Ⅱ)-催化芳胺C-H键与炔丙醇的高选择性[3+2]环化反应

  • 白丽丽 ,
  • 王颖 ,
  • 王烁今 ,
  • 孔杜林 ,
  • 付艳 ,
  • 彭德乾 ,
  • 文丽君 ,
  • 陈训
展开
  • 海南医学院药学院 海口 571199

收稿日期: 2018-06-25

  修回日期: 2018-07-23

  网络出版日期: 2018-08-23

基金资助

海南省科协青年科技英才学术创新计划(Nos.QCXM201808,QCXM201707)资助项目.

Ruthenium(Ⅱ)-Catalyzed C-H Bond Regioselective[3+2] Annulation of Arylamines with Propargyl Alcohols

  • Bai Lili ,
  • Wang Ying ,
  • Wang Shuojin ,
  • Kong Dulin ,
  • Fu Yan ,
  • Peng Deqian ,
  • Wen Lijun ,
  • Chen Xun
Expand
  • School of Pharmacy, Hainan Medical University, Haikou 571199

Received date: 2018-06-25

  Revised date: 2018-07-23

  Online published: 2018-08-23

Supported by

Project supported by the Program of Hainan Association for Science and Technology Plans to Youth R & D Innovation (Nos. QCXM201808, QCXM201707).

摘要

报道了一种简便有效的Ru(Ⅱ)-催化芳胺C-H键与炔丙醇的高选择性[3+2]环化反应,能够高效构建含有羟基功能基的吲哚骨架结构,为进一步衍生更加复杂有用的药物分子提供简便的合成渠道.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键活化可能属于整个反应历程的决速步骤.

本文引用格式

白丽丽 , 王颖 , 王烁今 , 孔杜林 , 付艳 , 彭德乾 , 文丽君 , 陈训 . 钌(Ⅱ)-催化芳胺C-H键与炔丙醇的高选择性[3+2]环化反应[J]. 有机化学, 2018 , 38(12) : 3242 -3249 . DOI: 10.6023/cjoc201806039

Abstract

A simple and efficient ruthenium(Ⅱ)-catalyzed C-H bond regioselective[3+2] annulation of arylamines with propargyl alcohols has been reported. This protocol provides a facile approach to hydroxy-containing indole skeleton, which could be employed for constructing more complex and useful pharmaceutical molecules. Meantime, the kinetic isotope effect was further investigated and the results indicated that the C-H bond-breaking was possibly involved in the rate-limiting step of this transformation.

参考文献

[1] (a) Smart, B. P.; Oslund, R. C.; Walsh, L. A.; Gelb, M. H. J. Med. Chem. 2006, 49, 2858.
(b) Hu, W.; Guo, Z.; Chu, F.; Bai, A.; Yi, X.; Cheng, G.; Li, J. Bioorg. Med. Chem. 2003, 11, 1153.
(c) Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73.
(d) Kaushik, N.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C.; Verma, A.; Choi, E. Molecules 2013, 18, 6620.
[2] (a) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.
(b) Alexandre, F. R.; Amador, A.; Bot, S.; Caillet, C.; Convard, T.; Jakubik, J.; Musiu, C.; Poddesu, B.; Vargiu, L.; Liuzzi, M.; Roland, A.; Seifer, M.; Standring, D.; Storer, R.; Dousson, C. B. J. Med. Chem. 2011, 54, 392.
(c) Chiu, C. W.; Chow, T. J.; Chuen, C. H.; Lin, H. M.; Tao, Y. T. Chem. Mater. 2003, 15, 4527.
[3] (a) Reissert, A. Ber. Dtsch. Chem. Ges. 1897, 30, 1030.
(b) Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214.
(c) Patrick, J. B.; Saunders, E. K. Tetrahedron Lett. 1979, 4009.
(d) Gassman, P. G.; Roos, J. J.; Lee, S. J. J. Org. Chem. 1984, 49, 717.
(e) Furstner, A.; Ernst, A. Tetrahedron 1995, 51, 773.
[4] Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241.
[5] Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
[6] (a) Ramirez, T. A.; Zhao, B.; Shi, Y. Chem. Soc. Rev. 2012, 41, 931.
(b) Wang, S.; Yan, F.; Wang, L.; Zhu, L. Chin. J. Org. Chem. 2018, 38, 291(in Chinese). (汪珊, 严沣, 汪连生, 朱磊, 有机化学, 2018, 38, 291.)
(c) Chen, J.; Hu, X.; Lu, L.; Xiao, W. Chem. Rev. 2015, 115, 5301.
[7] (a) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007.
(b) Ackermann, L. Acc. Chem. Res. 2014, 47, 281.
(c) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
[8] (a) Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625.
(b) Wang, C.; Huang, Y. Org. Lett. 2013, 15, 5294.
(c) Liang, Y.; Jiao, N. Angew. Chem., Int. Ed. 2016, 55, 4035.
(d) Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764.
[9] (a) Han, Y.-P.; Song, X.-R.; Qiu, Y.-F.; Zhang, H.-R.; Li, L.-H.; Jin, D.-P.; Sun, X.-Q.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 940.
(b) Hosseyni, S.; Su, Y.; Shi, X. Org. Lett. 2015, 17, 6010.
(c) Song, X.-R.; Han, Y.-P.; Qiu, Y.-F.; Qiu, Z.-H.; Liu, X.-Y.; Xu, P.-F.; Liang, Y.-M. Chem.-Eur. J. 2014, 20, 12046.
(d) Zhang, X.; Teo, W. T.; Sally; Chan, P. W. H. J. Org. Chem. 2010, 75, 6290.
[10] Sen, M.; Dahiya, P.; Premkumar, J. R.; Sundararaju, B. Org. Lett. 2017, 19, 3699.
[11] (a) Chen, X.; Xie, Y.; Xiao, X.; Li, G.; Deng, Y.; Jiang, H.; Zeng, W. Chem. Commun. 2015, 51, 15328.
(b) Chen, X.; Hu, X.; Bai, S.; Deng, Y.; Jiang, H.; Zeng, W. Org. Lett. 2016, 18, 192.
(c) Chen, X.; Hu, X.; Deng, Y.; Jiang, H.; Zeng, W. Org. Lett. 2016, 18, 4742.
(d) Hu, X.; Chen, X.; Shao, Y.; Xie, H.; Li, G.; Deng, Y.; Ke, Z.; Jiang, H.; Zeng, W. ACS Catal. 2018, 8, 1308.
[12] (a) Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764;
(b) Wei, L.-M.; Wei, L.-L.; Pan, W.-B.; Wu, M.-J. Tetrahedron Lett. 2003, 44, 595.

文章导航

/