研究简报

溴呋啶及其类似物的合成新方法研究

  • 李培源 ,
  • 张建瑞 ,
  • 郭胜海 ,
  • 张新迎 ,
  • 范学森
展开
  • 河南师范大学化学化工学院 河南省精细化学品绿色制造协同创新中心 新乡 453007

收稿日期: 2014-10-24

  修回日期: 2014-11-22

  网络出版日期: 2014-12-09

基金资助

国家自然科学基金(Nos. 21172057, 21272058, 21202040)及教育部博士点基金(No. 20114104110005)资助项目.

New Synthesis of Brivudine and Its Analogs

  • Li Peiyuan ,
  • Zhang Jianrui ,
  • Guo Shenghai ,
  • Zhang Xinying ,
  • Fan Xuesen
Expand
  • School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals, Henan Normal University, Xinxiang 453007

Received date: 2014-10-24

  Revised date: 2014-11-22

  Online published: 2014-12-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172057, 21272058, 21202040), and the Research Fund for the Doctoral Program of Higher Education (No. 20114104110005).

摘要

以5-甲酰基嘧啶核苷为原料, 先经与四溴化碳缩合得5-(2,2-二溴乙烯基)嘧啶核苷类似物, 然后在亚磷酸二乙酯和三乙胺的作用下发生立体选择性脱溴反应, 高效合成了溴呋啶及其类似物.

本文引用格式

李培源 , 张建瑞 , 郭胜海 , 张新迎 , 范学森 . 溴呋啶及其类似物的合成新方法研究[J]. 有机化学, 2015 , 35(4) : 910 -916 . DOI: 10.6023/cjoc201410034

Abstract

In this paper, a simple and practical method for the preparation of brivudine (BVDU) and its analog nucleoside derivatives via condensation of the easily obtainable 5-formyl pyrimidine nucleosides with carbon tetrabromide followed by an efficient and stereoselective debromination promoted by diethyl phosphite and triethylamine is presented.

参考文献

[1] (a) Jordheim, L. P.; Durantel, D.; Zoulim, F.; Dumontet, C. Nat. Rev. Drug Discovery 2013, 12, 447.
(b) Wainberg, M. A. Antiviral Res. 2009, 81, 1.
(c) Jin, Y.-Y.; Xiao, Q.; Jv, Y. Chin. J. Org. Chem. 2009, 29, 44 (in Chinese).
(靳玄烨, 肖强, 巨勇, 有机化学, 2009, 29, 44.)
(d) Menéndez-Arias, L.; álvarez, M.; Pacheco, B. Curr. Opin. Virol. 2014, 8, 1.
[2] (a) Xia, Y.; Liu, Y.; Rocchi, P.; Wang, M.; Fan, Y.; Qu, F.; Iovanna, J. L.; Peng, L. Cancer Lett. 2012, 318, 145.
(b) Wu, J.; Yu, W.; Fu, L.; He, W.; Wang, Y.; Chai, B.; Song, C.; Chang, J. Eur. J. Med. Chem. 2013, 63, 739.
(c) Shirouzu, H.; Morita, H.; Tsukamoto, M. Tetrahedron 2014, 70, 3635.
[3] (a) Wainberg, M. A. Antiviral Res. 2009, 81, 1.
(b) De Clercq, E. Rev. Med. Virol. 2009, 19, 287.
(c) De Clercq, E. J. Med. Chem. 2010, 53, 1438.
(d) De Clercq, E. Antiviral Res. 2010, 85, 19.
[4] Bleackley, R. C.; Jones, A. S.; Walker, R. T. Tetrahedron 1976, 32, 2795.
[5] Ashwell, M.; Jones, A. S.; Kumar, A.; Sayers, J. R.; Walker, R. T.; Sakuma, T.; de Clercq, E. Tetrahedron 1987, 43, 4601.
[6] Wang, C. J.; Xie, F.; Zhang, W. B. Chin. J. Org. Chem. 2008, 28, 503 (in Chinese).
(王春娟, 谢芳, 张万斌, 有机化学, 2008, 28, 503.)
[7] Chelucci, G. Chem. Rev. 2012, 112, 1344 and references cited therein.
[8] (a) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. J. Org. Chem. 1981, 46, 3745.
(b) Abbas, S.; Hayes, C. J.; Worden, S. Tetrahedron Lett. 2000, 41, 3215.
[9] Fan, X. S.; Li, P. Y.; Li, K.; Zhang, X. Y.; Zhao, W. Chin. J. Org. Chem. 2014, 34, 999 (in Chinese).
(范学森, 李培源, 李坤, 张新迎, 赵婉, 有机化学, 2014, 34, 999.)
[10] Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
[11] (a) Wang, S. M.; Li, J.; Li, H. Y.; Liu, H. M.; Li, W. Chin. J. Org. Chem. 2008, 28, 120 (in Chinese).
(王少敏, 李娟, 李华雨, 刘宏民, 李雯, 有机化学, 2008, 28, 120.)
(b) Li, W.; Liu, H.-M.; You, Q.-D. Acta Chim. Sinica 2003, 61, 1516 (in Chinese).
(李雯, 刘宏民, 尤启东, 化学学报, 2003, 61, 1516.)

文章导航

/