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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (02): 249-255. 上一篇    下一篇

研究简报

利用Pummerer反应合成2-(2,6-二卤苯基)-3-(4,5,6-三甲基-2-嘧啶基)-5-酯酰氧基-1,3-噻唑烷-4-酮衍生物

陈华*，郭在红，殷庆梅，李小六*   

  1. (河北大学化学与环境科学学院 河北省化学生物学重点实验室 保定 071002)
  • 收稿日期:2010-06-17 修回日期:2010-09-29 发布日期:2010-10-09
  • 通讯作者: 陈华 E-mail:hua-todd@163.com

Synthesis of 2-(2,6-Dihalophenyl)-3-(4,5,6-trimethyl-pyrimidin-2-yl)- 4-oxothiazolidin-5-yl Carboxylates by Pummerer Reaction

CHEN Hua, GUO Zai-Hong, YIN Qing-Mei, LI Xiao-Liu   

  1. (Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002)
  • Received:2010-06-17 Revised:2010-09-29 Published:2010-10-09

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940

被引次数

2

利用Pummerer反应, 以有机酸为反应原料、溶剂和催化剂, 简便、高效地合成了一系列2-(2,6-二卤苯基)-3-(4,5,6-三甲基-2-嘧啶基)-5-酯酰氧基-1,3-噻唑烷-4-酮(7a～7g和8a～8g), 产率为62%～85%. X衍射确证化合物主要异构体的构型为噻唑烷-4-酮环C-5与C-2位取代基处于反式构型, 顺反异构体比例通过1H NMR确定. 化合物7a和8a具有中等强度的抗HIV-RT活性.

关键词: 噻唑烷-4-酮, 抗HIV活性, Pummerer反应

A series of novel 2-(2,6-dihalophenyl)-3-(4,5,6-trimethyl-pyrimidin-2-yl)-4-oxothiazolidin-5-yl carboxylate (7a～7g) and (8a～8g) were synthesized by Pummerer reaction in good yields (62%～85%) using the corresponding fatty acid as the reagent, catalyst and solvent. X-ray crystalographical analysis revealed that compounds 7 and 8 possessed the favored configuration: trans orientation on C-5 and C-2 at thiazolidin-4-one, and the ratios of trans to cis isomers in compounds 7 and 8 were determined by 1H NMR spectroscopy. Compounds 7a and 8a showed a moderate HIV-RT inhibitory activity.

Key words: thiazolidin-4-one, anti-HIV-RT activity, Pummerer reaction