Novel and Efficient Synthesis of 6-Bromofuro[2,3-d]pyrimidine Bicyclic Nucleosides

doi:10.6023/cjoc201311020

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 999-1005.DOI: 10.6023/cjoc201311020 Previous Articles Next Articles

Notes

6-溴代呋喃[2,3-d]嘧啶双环核苷的合成新方法研究

范学森^a, 李培源^a, 李坤^a,b, 张新迎^a, 赵婉^a

a 河南师范大学化学化工学院新乡 453007;
b 周口师范学院化学系周口 466000

收稿日期:2013-11-13 修回日期:2013-12-28 发布日期:2014-01-22
通讯作者: 范学森 E-mail:xuesen.fan@htu.cn
基金资助:
国家自然科学基金（Nos. 21172057，21272058）、教育部长江学者和创新团队发展计划（No. IRT 1061）、教育部博士点基金（No. 20114104110005）及国家大学生创新实验（No. 20120055）资助项目.

Novel and Efficient Synthesis of 6-Bromofuro[2,3-d]pyrimidine Bicyclic Nucleosides

Fan Xuesen^a, Li Peiyuan^a, Li Kun^a,b, Zhang Xinying^a, Zhao Wan^a

a School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007;
b Department of Chemistry, Zhoukou Normal University, Zhoukou 466000

Received:2013-11-13 Revised:2013-12-28 Published:2014-01-22
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172057, 21272058), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT) (No. IRT 1061), and the Research Fund for the Doctoral Program of Higher Education (RFDP) (No. 20114104110005).

6-Bromofuro[2,3-d]pyrimidine bicyclic nucleosides are the key intermediates for the preparation of novel furo[2,3-d]pyrimidine bicyclic nucleoside derivatives with remarkable antiviral potency. The literature protocol for their synthesis involves a multi-step procedure and palladium catalyst. In this paper, an economical and practical method for their preparation is developed via condensation of the easily obtainable 5-formyl pyrimidine nucleosides with carbon tetrabromide and subsequent cyclization promoted by copper iodide.

Key words: 6-bromofuro[2,3-d]pyrimidine bicyclic nucleosides, gem-dibromoalkenes, copper iodide

Cite this article

Fan Xuesen, Li Peiyuan, Li Kun, Zhang Xinying, Zhao Wan. Novel and Efficient Synthesis of 6-Bromofuro[2,3-d]pyrimidine Bicyclic Nucleosides[J]. Chin. J. Org. Chem., 2014, 34(5): 999-1005.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) De Clercq, E. Rev. Med. Virol. 2009, 19, 287.

(b) De Clercq, E. J. Med. Chem. 2010, 53, 1438.

[2] 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, 2010, 30, 797.)

[3] Topalis, D.; Pradère, U.; Roy, V.; Caillat, C.; Azzouzi, A.; Broggi, J.; Snoeck, R.; Andrei, G.; Lin, J.; Eriksson, S.; Alexandre, J. A. C.; El-Amri, C.; Deville-Bonne, D.; Meyer, P.; Balzarini, J.; Agrofoglio, L. A. J. Med. Chem. 2011, 54, 222.

[4] Srivastav, N. C.; Mak, M.; Agrawal, B.; Tyrrell, D. L. J.; Kumar, R. Bioorg. Med. Chem. Lett. 2010, 20, 6790.

[5] McGuigan, C.; Yarnold, C. J.; Jones, C.; Velázquez, S.; Barucki, H.; Brancale, A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1999, 42, 4479.

[6] Balzarini, J.; McGuigan, C. J. Antimicrob. Chemother. 2002, 50, 5.

[7] Janeba, Z.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Robins, M. J. J. Med. Chem. 2005, 48, 4690.

[8] Januszczyk, P.; Fogt, J.; Boryski, J.; Izawa, K.; Onishi, T.; Neyts, J.; De Clercq, E. Nucleosides Nucleotides Nucleic Acids 2009, 28, 713.

[9] Kifli, N.; De Clercq, E.; Balzarini, J.; Simons, C. Bioorg. Med. Chem. 2004, 12, 4245.

[10] Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854.

[11] Jin, Y.-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.)

[12] McGuigan, C.; Barucki, H.; Blewett, S.; Carangio, A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. J. Med. Chem. 2000, 43, 4993.

[13] De Clercq, E. Med. Res. Rev. 2009, 29, 571.

[14] Migliore, M. Antiviral Chem. Chemother. 2010, 20, 107.

[15] Robins, M. J.; Miranda, K.; Rajwanshi, V. K.; Peterson, M. A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. J. Med. Chem. 2006, 49, 391.

[16] Newman, S. G.; Aureggi, V.; Bryan, C. S.; Lautens, M. Chem. Commun. 2009, 5236.

[17] Chen, W.; Zhang, Y.-C.; Zhang, L.; Wang, M.; Wang, L. Chem. Commun. 2011, 10476.

[18] Fan, X.-S.; Wang, Y.-Y.; Qu, Y.-Y.; Xu, H.-Y.; He, Y.; Zhang, X.-Y.; Wang, J.-J. J. Org. Chem. 2011, 76, 982.

[19] Desai, N. B.; McKelvie, N.; Ramirez, F. J. Am. Chem. Soc. 1962, 84, 1745.Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.

6-溴代呋喃[2,3-d]嘧啶双环核苷的合成新方法研究

Novel and Efficient Synthesis of 6-Bromofuro[2,3-d]pyrimidine Bicyclic Nucleosides

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	Zhang Rui, Pan Jinhuan, Wu Qiongyou. Copper Mediated One-Pot Multi-Component Synthesis of 3-Substitued Isoquinolines [J]. Chin. J. Org. Chem., 2016, 36(12): 2906-2911.
[2]	Li Peiyuan, Zhang Jianrui, Guo Shenghai, Zhang Xinying, Fan Xuesen. New Synthesis of Brivudine and Its Analogs [J]. Chin. J. Org. Chem., 2015, 35(4): 910-916.