钯催化的基于C—H活化合成C-8位芳基取代嘌呤类似物
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
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).
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
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.
Key words: purine; C—H activation; aryl boric acid; arylation
[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.
/
| 〈 |
|
〉 |