研究简报

[Bmim]ZnBr3促进的烯胺酯和联烯酮的串联反应合成烟酸酯衍生物

  • 张涛 ,
  • 王强
展开
  • 河南理工大学化学化工学院 焦作 45400

收稿日期: 2017-09-13

  修回日期: 2017-10-17

  网络出版日期: 2017-10-31

基金资助

河南省教育厅自然科学技术研究重点(No.14A150048)资助项目.

[Bmim]ZnBr3-Promoted Tandem Reaction of Enaminoester and Allenic Ketones for the Synthesis of Substituted Nicotinate Derivatives

  • Zhang Tao ,
  • Wang Qiang
Expand
  • College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo 454000

Received date: 2017-09-13

  Revised date: 2017-10-17

  Online published: 2017-10-31

Supported by

Project supported by the Natural Science Research Program from Education Department of Henan Province (No. 14A150048).

摘要

发展了一种Lewis酸性离子液体[Bmim]ZnBr3促进的烯胺酯与联烯酮的新型串联反应,在二者缩合生成烟酸酯衍生物的过程中,这种离子液体既作为溶剂又起着催化剂的作用,并且可以回收再利用.该串联反应具有反应时间短、处理过程简单、环境友好、产率高等优点,可为含有烟酸酯结构单元的天然产物及复杂药物分子的合成提供简便的途径.

本文引用格式

张涛 , 王强 . [Bmim]ZnBr3促进的烯胺酯和联烯酮的串联反应合成烟酸酯衍生物[J]. 有机化学, 2018 , 38(2) : 498 -503 . DOI: 10.6023/cjoc201709019

Abstract

A novel approach for the synthesis of nicotinate derivatives has been developed by using Lewis acidic ionic liquid[Bmim]ZnBr3, which acts as dual solvent-catalyst in promoting the tandem reaction of enaminoester and allenic ketones. In the reaction process, no catalysts or other organic solvents are used, and[Bmim]ZnBr3 can be readily reused for three times without noticeable decrease in the catalytic activity after simple treatment. Furthermore, our method offers several advantages such as short reaction times, simple work-up procedure, environment-friendly solvent and good yields. The current methodology could also be conveniently applied to the synthesis of natural products and complex therapeutic agents occurring niacin frameworks.

参考文献

[1] (a) Sinthupoom, N.; Prachayasittikul, V.; Prachayasittikul, S.; Ruchirawat, S.; Prachayasittikul, V. Eur. Food. Res. Technol. 2015, 240, 1.
(b) Trabbic, C. J.; Zhang, F.; Walseth, T. F.; Slama, J. T. J. Med. Chem. 2015, 58, 3593.
(c) Ding, C. Curr. Opin. Invest. Drugs 2006, 7, 1020.
(d) Zhou, B.; Li, Z. -M.; Liu, C. -L.; Zhao, W. -G. Chin. J. Org. Chem. 2004, 24, 1304(in Chinese). (钟滨, 李正名, 刘长令, 赵卫光, 有机化学, 2004, 24, 1304.)
[2] (a) Hill, M. D. Chem. -Eur. J. 2010, 16, 12052.
(b) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
(c) Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642.
[3] (a) Hantzsch, A. Chem. Ber. 1881, 14, 1637.
(b) Xia, J. -J.; Wang, G. -W. Synthesis 2005, 2379.
(c) Abdel-Mohsen, H. T.; Conrad, J.; Beifuss, U. Green Chem. 2012, 14, 2686.
(d) DePaolis, O.; Baffoe, J.; Landge, S.; Török, B. Synthesis 2008, 3423.
(e) Chang, L. -M.; Lai, J. -Y.; Yuan, G. -Q. Chin. J. Chem. 2016, 34, 887.
[4] (a) Bagley, M. C.; Dale, J. W.; Bower, J. Synlett 2001, 1149.
(b) Bagley, M. C.; Dale, J. W.; Bower, J. Chem. Commun. 2002, 1682.
(c) Bagley, M. C.; Glover, C.; Merritt, E. A. Synlett 2007, 2459.
[5] Chun, Y. -S.; Lee, J. -H.; Kim, J. -H.; Ko, Y. -O.; Lee, S. Org. Lett. 2011, 13, 6390.
[6] Al-Saleh, B.; Abdelkhalik, M. M.; Eltoukhy, A. M.; Elnagdi, M. H. J. Heterocycl. Chem. 2002, 39, 1035
[7] Muller, F.; Allais, C.; Constantieux, T.; Rodriguez, J. Chem. Commun. 2008, 4207.
[8] Allais, C.; Constantieux, T.; Rodriguez, J. Chem. -Eur. J. 2009, 15, 12945.
[9] Zhao, Y. -Y.; Wang, E. -B.; Wang, Y. -L. Chin. J. Org. Chem. 2017, 37, 866(in Chinese). (赵玉英, 王二兵, 王颖莉, 有机化学, 2017, 37, 866.)
[10] Stanforth, S. P.; Tarbitb, B.; Watsona, M. D. Tetrahedron 2004, 60, 8893.
[11] Chibiryaev, A. M.; Kimpe, N. D.; Tkachev, A. V. Tetrahedron Lett. 2000, 41, 8011.
[12] (a) Kumar, S.; Sawant, A. A.; Chikhale, R. P.; Karanjai, K.; Thomas, A. J. Org. Chem. 2016, 81, 1645.
(b) Kiss, L. E.; Ferreira, H. S.; Learmonth, D. A. Org. Lett. 2008, 10, 1835.
[13] (a) Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett. 2008, 10, 2629.
(b) Tejedor, D.; Méndez-Abt, G.; García-Tellado, F. Eur. J. Org. Chem. 2010, 6582.
[14] (a) Li, L. -T.; Ma, S. -M. Chin. J. Org. Chem. 2000, 20, 850(in Chinese). (李林涛, 麻生明, 有机化学, 2000, 20, 850.)(b) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
(c) Fan, X.; He, Y.; Zhang, X. Chem. Rec. 2016, 16, 1635.
(d) Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074.
[15] Ma, S. -M.; Yin, S. -H.; Li, L. -T.; Tao, F. -G. Org. Lett. 2002, 4, 505.
[16] (a) Zhang, X.; Jia, X.; Fang, L.; Liu, N.; Wang, J.; Fan, X. Org. Lett. 2011, 13, 5024.
(b) He, Y.; Zhang, X.; Fan, X. Chem. Commun. 2014, 50, 14968.
(d) Zhang, X.; Song, Y.; Gao, L.; Guo, X.; Fan, X. Org. Biomol. Chem. 2014, 12, 2099.
(e) Fan, X.; Yan, M.; Wang, Y.; Zhang, X. J. Org. Chem. 2015, 80, 10536.
[17] Wang, Q.; Xu, Z.; Fan, X. -S. RSC Adv. 2013, 3, 4156.
[18] Wang, Q.; Yang, L.; Fan, X. -S. Synlett 2014, 25, 687.
[19] (a) Karthikeyan, G.; Perumal, P. T. J. Heterocycl. Chem. 2004, 41, 1039.
(b) Kamakshi, R.; Reddy, B. S. R. Aust. J. Chem. 2006, 59, 463.
[20] (a) Ramtohul, Y. K.; Chartrand, A. Org. Lett. 2007, 9, 1029.
(b) Zhao, M. -N.; Liang, H.; Ren, Z. -H.; Guan, Z. -H. Adv. Synth. Catal. 2013, 355, 221.
[21] (a) Sniady, A.; Morreale, M. S.; Dembinski, R. Org. Synth. 2007, 84, 199.
(b) Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328.
[22] Lecocq, V.; Graille, A.; Santini, C. C.; Baudouin, A.; Chauvin, Y.; Basset, J. M.; Arzel, L.; Bouchu, D.; Fenet, B. New J. Chem. 2005, 29, 700.

文章导航

/