Indium‐mediated facile preparation of 2‐(heterocyclic thio)‐1‐(2,3,4‐trimethoxyphenyl)ethanone in aqueous media

Abstract

An environmentally benign and efficient process for the preparation of 1‐(2,3,4‐trimethoxyphenyl)‐2‐substituted heterocyclic thio ethanone derivatives was achieved by the reactions of mercapto compounds with 2‐bromo‐1‐(2,3,4‐trimethoxyphenyl)ethanone in water mediated by indium in very high yields. Antifungal activities of the compounds were examined and moderate activity was obtained.

Synthesis and biological activity of novel 1‐(2,3,4‐trimethoxyphenyl)‐2‐{[5‐(3,4,5‐trimethoxyphenyl)‐1,3,4‐thiadiazol‐2‐yl]thio}ethanone oxime ester derivatives

“…The infrared spectra were recorded on a Bruker VECTOR22 spectrometer in KBr disks. 1 H NMR (solvent CDCl 3 ) and 13 C NMR spectra (solvent CDCl 3 ) were performed on a Varian-INOVA 400 MHz spectrometer at room temperature using TMS as internal standard. The mass spectra were taken on an HP5988A spectrometer.…”

“…Considered that 1,3,4-thiadiazole compounds tend to contain multi-structure in a molecule, the biological activity of these compounds may be improved by the promotion of these combination with the cell's microstructure and the accumulation of various biological activities resulting from the incorporation of different heterocyclic and non-heterocyclic nucleated changes on biological activity of the compounds [6][7][8]. In our previous work in it, we reported that some 2-(1H-1, 2, 4-triazol)-1-(2,3,4-trimethoxyphenyl)ethanoxime ester derivatives showed fungicidal activities [9][10][11][12][13][14]. Based on the theory of structure-activity relationship, we modified these structures by replacement of 1,2,4-triazole with benzothiazole group and found that some of them still kept high virucidal activities.…”

“…The title compounds were identified by IR, 1 H NMR, 13 C NMR and elemental analysis. The bioassay tests showed that these title compounds exhibit weak to moderate anticancer activity in vitro by MTT method.…”

Novel 2,4,5-trisubstituted oxazole derivatives: Synthesis and antiproliferative activity

“…1,2,3-trimethoxybenzene (1) was prepared from pyrogallol etheration [15], substituted acetophenone (2) was prepared from trimethoxybenzene and acetic anhydride via Friedel-Crafts acetylation reaction [16], while compound 3 was synthesized by bromination of substituted acetophenone (2). The ethanone 4a was prepared by alkylation of thioles [17,18]. The reaction of compound 4 with hydroxylamine was carried out in methanol catalyzed by pyridine to produce compound 5, and the reaction was completed within 5 h at refluxing temperature [19,20].…”

Indium Trichloride‐Mediated Facile Synthesis of 3‐(Substituted methylthio)‐4‐phenyl‐5‐(3,4,5‐trimethoxyphenyl)‐4H‐1,2,4‐triazole in Water†

“…10 In our effort to develop a new strategy for the synthesis of thioether derivatives, we studied the one-pot indiummediated thioetherification reaction of 2-(heterocyclic thio)-1-(2,3,4-trimethoxyphenyl)ethanone in aqueous media. 11 In this paper, we would like to report a new green method for synthesizing the title compound with indium trichloride used as catalyst to promote the formation of thioether derivatives containing 1,2,4-triazole moiety at room temperature in aqueous media. This method was easily in process, mild in condition, environmentally friendly and high yielding.…”