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Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (02): 249-255. Previous Articles Next Articles
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陈华*,郭在红,殷庆梅,李小六*
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CHEN Hua, GUO Zai-Hong, YIN Qing-Mei, LI Xiao-Liu
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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
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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