SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 02: 378 - 382

DOI: https://doi.org/10.6023/cjoc201210031

研究简报

4-(1H)-喹诺酮及甲氧基和溴代衍生物的合成研究

  • 马梦林 ,
  • 黄剑彪 ,
  • 王玉良 ,
  • 陈淑华 ,
  • 陈华
展开
  • a 西华大学物理与化学学院 成都 610039;
    b 四川大学化学学院 教育部绿色化学重点实验室 成都 610064;
    c 上海大学理学院 上海200444

收稿日期: 2012-10-17

  修回日期: 2012-11-05

  网络出版日期: 2012-11-15

基金资助

国家自然科学基金(No. B020601);四川省自然科学重点基金(No. 07ZA109)资助项目.

收起

Syntheses of 4-(1H)-Quinolones and the Brominated or Methoxy Substituted Derivatives

  • Ma Menglin ,
  • Huang Jianbiao ,
  • Wang Yuliang ,
  • Chen Shuhua ,
  • Chen Hua
Expand
  • a School of Physics and Chemistry, Xihua University, Chengdu 610039;
    b Key Laboratory of Green Chemistry and Technology of Ministry of Education, Faculty of Chemistry, Sichuan University, Chengdu 610064;
    c College of Science, Shanghai University, Shanghai 200444

Received date: 2012-10-17

  Revised date: 2012-11-05

  Online published: 2012-11-15

Supported by

Project supported by the National Natural Science Foundation of China (No. B020601), the Natural Science Foundation of Sichuan Province (No. 07ZA109).

Fold

摘要

提出了一种4-(1H)-喹诺酮衍生物合成方法. 以3,3-二乙氧基丙酸乙酯和苯胺为原料, 生成中间体3-(苯基亚氨基)丙酸乙酯, 再经热环化或微波促进环化两步反应制备4-(1H)-喹诺酮, 并以此方法合成了7个溴代或甲氧基取代的4-(1H)-喹诺酮衍生物.

关键词： 4-(1H)-喹诺酮; 3,3-二乙氧基丙酸乙酯; 合成方法; 环化

本文引用格式

马梦林 , 黄剑彪 , 王玉良 , 陈淑华 , 陈华 . 4-(1H)-喹诺酮及甲氧基和溴代衍生物的合成研究[J]. 有机化学, 2013 , 33(02) : 378 -382 . DOI: 10.6023/cjoc201210031

Abstract

A simple and new synthetic approach to 4-(1H)-quinolones was described. This method was started from ethyl 3,3-diethoxypropanoate and aniline via a synthetic sequence of preparation of key intermediate 3-(phenylimino)propionate and cyclization reaction. The brominated or methoxy substituted derivatives were synthesized by this new method as well.

Key words： 4(1H)quinolones, 3,3-diethoxypropanoate; synthetic method; cyclization

参考文献

[1] Reitsema, R. H. Chem. Rev. 1948, 43, 43.

[2] (a) Jong, Y. H.; Takashi, K.; David, J. L.; Julie, A. C.; Kiplin, G. J. Med. Chem. 2011, 54, 7084.
(b) Dibyendu, D.; Frances, M. K.; Larry, D. B.; Donald, J. K. J. Med. Chem. 1998, 41, 4918.
(c) Peter, B. M.; John, S.; Ally P. L.; Kiplin, G. B ioorg. Med. Chem. Lett. 2005, 15, 1015.
(d) Hiroshi, S.; Nagwa, S. M.; Yusuke, W. Chem. Pharm. Bull. 2007, 55(5), 821.

[3] (a) Takayuki, F.; Teruyuki, S.; Terufumi, S.; Tatsushi, O. J. Med. Chem. 2006, 49, 2186.
(b) Kazuo, K.; Ohyama, S. I.; Toshiyuki, S.; Atsuya T. B ioorg. Med. Chem. Lett. 2003, 11, 5117.

[4] Balaram, G.; Tamara, A.; Maarten, E. A. R.; Aloke, K. D. J. Med. Chem. 2010, 53, 2114.

[5] Nolt, M. B.; Zhao, Z. J.; Wolkenberg, S. E. Tetrahedron Lett. 2008, 49, 3137.

[6] Laurent, G.; Michael, D. H.; Wu, J. J.; John, J. M. B ioorg. Med. Chem. L ett. 2007, 17, 2723.

[7] (a) Cilirles, C. P.; Ruystun, M. K. J. Am. Chem. Soc. 1946, 68, 1204.
(b) Byron, R.; Gerald, R. L.; Bernard, H. A. J. Am. Chem. Soc. 1946, 68, 1264.

[8] László, L.; Tibor, Z. N.; Gellért, S.; Richard, J.; György, D. Tetra. Lett. 2012, 53, 738.

[9] (a) Brandon, J. M.; Kimberly, A. L.; Dana, L. T. J. Org. Chem. 2007, 72, 2232.
(b) Raul, C.; Ricardo, T.; Valderrama, J. A. Synth. Commun. 1985, 15(2), 125.

[10] Huang, X.; Liu, Z. X. Tetrahedron Lett. 2001, 42, 7655.

[11] Wang, J.; Jiang, F. C. Chin. J. Org. Chem. 2002, 22, 135 (in Chinese). (王静, 姜凤超, 有机化学, 2002, 22, 135.)

[12] (a) Badger, G. M.; Crocker, H. P.; Ennis, B. C. Aust. J. Chem. 1963, 16, 814, 840.
(b) Badger, G. M.; Ennis, B. C.; Matthews, W. E. Aust. J. Chem. 1963, 16, 828.

[13] Bergstroem, F. W. Chem. Rev. 1944, 35, 156.

[14] Sabine, P.; Glenn, D. WO 2006021448, 2006 [Chem. Abstr. 2006, 144, 274309].

[15] Duffy, K. J.; Chai, D. P.; Colon, M.; Fitch, D. M.; King, S. R.; Shaw, A. N.; Tedesco, R.; Wiggall, K. WO 2006132739, 2006[Chem. Abstr. 2006, 146, 62743].

[16] Breault, G.; Eyermann, C. J.; Geng, B.; Morningstar, M.; Reck, F. WO 2006134378, 2006[Chem. Abstr. 2006, 146, 81779].

[17] Prince, R. B.; Merrill, B. A.; Kshirsagar, T. A.; Heppner, P. D. WO 2006093514, 2006[Chem. Abstr. 2006, 145, 314981].
Options
文章导航

/

〈 〉