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

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (02): 249-255. Previous Articles Next Articles

Notes

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*

(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

(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

Abstract

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

Cite this article

CHEN Hua, GUO Zai-Hong, YIN Qing-Mei, LI Xiao-Liu. Synthesis of 2-(2,6-Dihalophenyl)-3-(4,5,6-trimethyl-pyrimidin-2-yl)- 4-oxothiazolidin-5-yl Carboxylates by Pummerer Reaction[J]. Chin. J. Org. Chem., 2011, 31(02): 249-255.

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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

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

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