研究简报

钯催化的基于C—H活化合成C-8位芳基取代嘌呤类似物

  • 牛红英 ,
  • 苏凌云 ,
  • 张齐齐 ,
  • 张婉娜 ,
  • 付红岩 ,
  • 李建平 ,
  • 渠桂荣 ,
  • 郭海明
展开
  • a 河南科技学院化学化工学院 新乡 453003;
    b 河南师范大学化学与化工学院 新乡 453007

收稿日期: 2014-11-25

  修回日期: 2014-12-29

  网络出版日期: 2015-01-09

基金资助

国家自然科学基金(Nos.21272059,21202039,21472037)、河南省高校科技创新人才支持计划(No.13HASTIT013)、国家大学生创新训练计划(No.201310467062)资助项目.

Pt Catalyzed C—H Activation of Purines and Aryl Boric Acids to 8-Aryl Purine Analogues

  • Niu Hongying ,
  • Su Lingyun ,
  • Zhang Qiqi ,
  • Zhang Wanna ,
  • Fu Hongyan ,
  • Li Jianping ,
  • Qu Guirong ,
  • Guo Haiming
Expand
  • a School of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang 453003;
    b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007

Received date: 2014-11-25

  Revised date: 2014-12-29

  Online published: 2015-01-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos.21272059, 21202039, 21472037), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No.13HASTIT013), and the National Training Programs of Innovation for Undergraduates (No.201310467062).

摘要

以芳基硼酸为芳基化试剂, 以Pd(PPh3)4为催化剂, CuI为添加剂, 哌啶为碱, 在DMF中于125 ℃反应24 h, 通过C—H键的活化反应, 合成了系列C-8位芳基取代的嘌呤类似物, 为该类化合物的合成提供了新的合成路线.

本文引用格式

牛红英 , 苏凌云 , 张齐齐 , 张婉娜 , 付红岩 , 李建平 , 渠桂荣 , 郭海明 . 钯催化的基于C—H活化合成C-8位芳基取代嘌呤类似物[J]. 有机化学, 2015 , 35(5) : 1156 -1160 . DOI: 10.6023/cjoc201411040

Abstract

C-8 aryl substituted purine analogues were successfully synthesized by direct C—H activation of purines with aryl boric acids catalyzed by Pd(PPh3)4 in the presence of CuI and piperidine in DMF at 125 ℃ for 24 h, providing a new process for the syn-thesis of 8-aryl purines.

参考文献

[1] (a) Schinazi, R. F.; Hernandez-Santiago, B. I.; Hurwitz, S. J. Antiviral Res. 2006, 71, 322. (b) Chu, C. K. Recent Advances in Nucleosides: Chemistry and Chemotherapy, Elsevier, Amsterdam, 2002. (c) Liu, Y. J.; Guo, X. H.; Bai, P. Chin. J. Org. Chem. 2014, 34, 2202 (in Chinese). (刘亚君, 郭翔海, 白鹏, 有机化学, 2014, 34, 2202.) (d) Zhang, X. Y.; Wang, Y. Y.; Feng, D.; Fan X. S. Chin. J. Org. Chem. 2010, 30, 797 (in Chinese). (张新迎, 王洋洋, 冯东, 范学森, 有机化学, 2014, 30, 797.) (e) Jin, X. Y.; Xiao, Q.; Ju, Y. Chin. J. Org. Chem. 2009, 29, 44 (in Chinese). (靳玄烨, 肖强, 巨勇, 有机化学, 2009, 29, 44.)
[2] (a) Kohda, K.; Tsunomoto, H.; Kasamatsu, T.; Sawamura, F.; Tcrashima, I.; Shibutani, S. Chem. Res. Toxicol. 1997, 10, 1351. (b) Gannett, P. M.; Powell, J. H.; Rao, R.; Shi X.; Lawson, T.; Kolar, C.; Toth, B. Chem. Res. Toxicol. 1999, 12, 297. (c) Dai, Q.; Xu, D. W.; Lim, K.; Harvey, R. G. J. Org. Chem. 2007, 72, 4856.
[3] (a) Sessler, J. L.; Jayawickramarajah, J. Chem. Commun. 2005, 1939. (b) Sessler, J. L.; Lawrence, C. M.; Jayawickramarajah, J. Chem. Soc. Rev. 2007, 36, 314. (c) Sessler, J. L.; Jayawickramarajah, J.; Sherman, C. L.; Brod-belt, J. S. J. Am. Chem. Soc. 2004, 126, 11460. (d) Sessler, J. L.; Sathiosatham, M.; Brown, C. T.; Rhodes, T. A.; Wiederrecht, G. J. Am. Chem. Soc. 2001, 123, 3655. (e) Gubala, V.; Betancourt, J. E.; Rivera, J. M. Org. Lett. 2004, 6, 4735.
[4] (a) Wu, T. F.; Froeyen, M.; Schepers, G.; Mullens, K.; Rozenski, J.; Busson, R.; Aerschot, A. V.; Herdewijn, P. Org. Lett. 2004, 6, 51. (b) Western, E. C.; Daft, J. R.; Johnson, E. M.; Gannett, P. M.; Shaughnessy, K. H. J. Org. Chem. 2003, 68, 6767. (c) ?apek, P.; Pohl, R.; Hocek, M. Org. Biomol. Chem. 2006, 4,2278. (d) Collier, A.; Wagner, G. Org. Biomol. Chem. 2006, 4, 4526.
[5] Kle?ka, M.; Pohl, R.; Klepetá?ová, B.; Hocek, M. Org. Biomol. Chem. 2009, 7, 866.
[6] (a) ?erňa, I.; Pohl, R.; Klepetá?ová, B.; Hocek, M. Org. Lett. 2006, 8, 5389. (b) ?erňa, I.; Pohl, R.; Hocek, M. Chem. Commun. 2007, 47, 4729. (c) Sahnoun, S.; Messaoudi, S.; Peyrat, J. F.; Brion J. D.; Alami, M. Tetrahedron Lett. 2008, 49, 7279. (d) Storr, T. E.; Firth, A. G.; Wilson, K.; Darley, K.; Baumann, C. G.; Fairlamb, I. J. S. Tetrahedron 2008, 64, 6125. (e) Sahnoun, S.; Messaoudi, S.; Brion, J. D.; Alami, M. Org. Biomol. Chem. 2009, 7, 4271.
[7] Qu, G. R.; Xin, P. Y.; Niu H.Y.; Wang, D. C.; Ding, R. F.; Guo, H. M. Chem. Commun. 2011, 47, 11140.
[8] (a) Niu, H. Y.; Yuan, T. F.; Qu, G. R.; Li, D. Y.; Mao, R. Z.; Jin, X.; Yang, X. N.; Guo, H.M. Chin. J. Org. Chem. 2011, 31, 1613 (in Chinese). (牛红英, 袁腾飞, 渠桂荣, 李德阳, 毛润泽, 金鑫, 杨西宁, 郭海明, 有机化学, 2011, 31, 1613.) (b) Niu, H. Y.; Zhang, X. T.; Zhao, G. Y.; Li, N.; Kong, S. N.; Xia, C.; Qu, G. R.; Guo, H. M. Chin. J. Org. Chem. 2011, 31, 695 (in Chinese). (牛红英, 张晓婷, 赵改云, 李宁, 孔思楠, 夏超, 渠桂荣, 郭海明, 有机化学, 2011, 31, 695.) (c) Wang, D. C.; Niu, H. Y.; Guo, H. M.; Wei, X. J.; Ding, R. F.; Qu, G. R. Chin. J. Org. Chem. 2012, 32, 1072 (in Chinese). (王东超, 牛红英, 郭海明, 魏雪娇, 丁瑞芳, 渠桂荣, 有机化学, 2011, 32, 1072.) (d) Wang, D. C.; Niu, H. Y.; Xie, M. S.; Qu, G. R.; Wang, H. X.; Guo, H. M. Org. Lett. 2014, 16, 262. (e) Xia, R.; Niu, H. Y.; Qu, G. R.; Guo, H. M. Org. Lett. 2012, 14, 5546. (f) Niu, H. Y.; Bai, S. X.; Wu, S.; Qu, G. R.; Guo, H. M. Asian J. Org. Chem. 2012, 1, 238. (g) Liu, J. Y.; Niu, H. Y.; Wu, S.; Qu, G. R.; Guo, H. M. Chem. Commun. 2012, 48, 9723. (h) Meng, G.; Niu, H. Y.; Qu, G. R.; Fossey, J. S.; Li, J. P.; Guo, H. M. Chem. Commun. 2012, 48, 9601.
[9] (a) Huang, L. K.; Cherng, Y. C.; Cheng, Y. R.; Jang J. P.; Chao Y. L.; Cherng Y. J. Tetrahedron 2007, 63, 5323. (b) Qu, G. R.; Xin, P. Y.; Niu, H. Y.; Jin, X.; Guo, X. T.; Yang, X. N.; Guo, H. M. Tetrahedron 2011, 67, 9099.

文章导航

/