研究论文

硫酸铈介导下黄酮和2-芳基-4-喹啉酮衍生物的合成

  • 刘瑞环 ,
  • 王绪礼 ,
  • 成飞 ,
  • 李福双 ,
  • 徐康平 ,
  • 谭桂山
展开
  • a 中南大学药学院 长沙 410013;
    b 中南大学湘雅医院 长沙 410013

收稿日期: 2016-03-22

  修回日期: 2016-06-20

  网络出版日期: 2016-07-08

基金资助

国家自然科学基金(No.31370370)、湖南省科技厅科技计划项目(No.2013SK5077)及海南省社会发展科技专项(No.SF201419)资助项目.

Ce(SO4)2·4H2O Mediated Synthesis of Flavones and 2-Phenyl-4-quinolones

  • Liu Ruihuan ,
  • Wang Xuli ,
  • Cheng Fei ,
  • Li Fushuang ,
  • Xu Kangping ,
  • Tan Guishan
Expand
  • a Department of Pharmacy, Central South University, Changsha 410013;
    b Xiangya Hospital, Central South University, Changsha 410013

Received date: 2016-03-22

  Revised date: 2016-06-20

  Online published: 2016-07-08

Supported by

Project supported by the National Natural Science Foundation of China (No.31370370),the Science and Technology Planning Project of Hunan Pprovince (No.2013SK5077) and the Social Development of Science and Technology Project of Hainan Province (No.SF201419)

摘要

报道了一种简便高效地构建黄酮及喹啉酮衍生物的方法.实验发现,以廉价易得的四水合硫酸化铈[Ce(SO42·4H2O]作为氧化剂,2'-羟基査尔酮或2'-氨基查尔酮为原料,在二甲基亚砜(DMSO)中,110℃下,环合生成相应的黄酮和喹啉酮衍生物.其特点是原料易得、价格低廉、反应条件温和及收率高.

本文引用格式

刘瑞环 , 王绪礼 , 成飞 , 李福双 , 徐康平 , 谭桂山 . 硫酸铈介导下黄酮和2-芳基-4-喹啉酮衍生物的合成[J]. 有机化学, 2016 , 36(11) : 2677 -2682 . DOI: 10.6023/cjoc201603036

Abstract

A simple and powerful procedure for the synthesis of flavones and quinolones was developed by using Ce(SO4)2·4H2O as oxidant, readily available 2'-hydroxychalcones and 2'-aminochalcones as raw materials, and dimethyl sulfoxide (DMSO) as solvent at 110℃. The new procedure is characterized with raw material easy to get, low manufacturing cost, mild reaction condi-tions and high yields.

参考文献

[1] Silva, A. M. S.; Pinto, D. C. G. A.; Cavaleiro, J. A. S. Tetrahedron Lett. 1994, 35, 5899.
[2] Akama, T.; Shida, Y.; Sugaya, T.; Ishida, H.; Gomi, K.; Kasai, M. J. Med. Chem. 1996, 39, 3461.
[3] Alam, S.; Sarkar, Z.; Islam, A. J. Chem. Sci. 2004, 116, 29.
[4] Hans, N.; Grover, S. K. Synth. Commun. 1993, 23, 1021.
[5] Donnelly, J. A.; Farrell, D. F. J. Org. Chem. 1990, 55, 1757.
[6] Ahmed, N.; Ali, H.; van Lier, J. E. Tetrahedron Lett. 2005, 46, 253.
[7] Jung, S-H.; Cho, S-H.; Dang, T. H.; Lee, J-H.; Ju, J-H.; Kim, M-K.; Lee, S-H.; Ryu, J-C.; Kim, Y. Eur. J. Med. Chem. 2003, 38, 537.
[8] Du, Z.; Ng, H.; Zhang, K.; Zeng, H.; Wang, J. Org. Biomol. Chem. 2011, 9, 6930.
[9] Tang, E.; Chen, B.; Zhang, L.; Li, W.; Lin, J. Synlett 2011, 707.
[10] Ahmed, N.; van Lier, J. E. Tetrahedron Lett. 2007, 48, 13.
[11] Kim, D.; Ham, K.; Hong, S. Org. Biomol. Chem. 2012, 10, 7305.
[12] Wu, X.-F.; Neumann, H.; Beller, M. Chem. Eur. J. 2012, 18, 12595.
[13] Yatabe, T.; Jin, X.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2015, 54, 13302.
[14] Ma, M.-L.; Li, M.; Gou, J.-J.; Ruan, T.-Y.; Jin, H.-S.; Zhang, L.-H.; Wu, L.-C.; Li, X.-Y.; Hu, Y.-H.; Zhao, Z. Bioorg. Med. Chem. 2014, 22, 6117.
[15] Huang, X.; Tang, E.; Xu, W.-M.; Cao, J. J. Comb. Chem. 2005, 7, 802.
[16] Guz, N. R.; Stermitz, F. R.; Johnson, J. B.; Beeson, T. D.; Willen, S.; Hsiang, J-F.; Lewis, K. J. Med. Chem. 2001, 44, 261.
[17] Lin, Y.; Zhou, Y.; Flavin, M. T.; Zhou, L.; Nie, W.; Chen, F. Bioorg. Med. Chem. 2002, 10, 2795.
[18] Hu, W.; Lin, J. P.; Song, L. R.; Long, Y. Q. Org. Lett. 2015, 17, 1268.
[19] An, Z.-Y.; Yan, Y.-Y.; Peng, D.; Ou, T.-M.; Huang, S.-L.; An, L.-K.; Gu, L.-Q.; Huang, Z.-S. Eur. J. Med. Chem. 2010, 45, 3895.
[20] Ding, D.; Li, X.; Wang, X.; Du, Y.; Shen, J. Tetrahedron Lett. 2006, 39, 6997.
[21] Huang, J.; Chen, Y.; King, A. O.; Dilmeghani, M.; Larsen, R. D.; Faul, M. M. Org. Lett. 2008, 10, 2609.
[22] Jones, C. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2007, 72, 7968.
[23] Sun, F.; Zhao, X.; Shi, D. Tetrahedron Lett. 2011, 52, 5633.

文章导航

/