Abstract
Aryl-2-sulfanylpropenoic acids 1a-d react with trichloroacetonitrile under various reaction conditions to give different products. Thus, reaction of 1a-d with trichloroacetonitrile in absolute ethanol and in the presence of few drops of triethylamine at room temperature affords 1,3- oxathiolan-5-one derivatives 4a-d. Whereas, compounds 1a-d react with trichloroacetonitrile in primary alcohols under reflux to afford the corresponding 2-alkoxy-2-trichloromethylthiazolidin- 4-one derivatives 7a-l. Reaction of compounds 1a-d with trichloroacetonitrile or other nitriles 11a-c in refluxing glacial acetic acid gave 5-arylmethylene-2,4-thiazolidinediones 8a-d. The structures of all the newly synthesized products were confirmed based on elemental and spectral data, and a plausible mechanism is postulated to account for their formation. X-ray crystallography was carried out for the products 4a and 7b.
Highlights
3-Aryl-2-sulfanylpropenoic acids are used as intermediates for the synthesis of a variety of heterocyclic sulfur compounds.[1,2,3,4,5]
An earlier investigation indicated that post-cadmium exposure treatment with certain 3aryl-2-sulfanylpropenoic acids is effective in decreasing liver and kidney cadmium burden in rats.7 3-Aryl-2-sulfanylpropenoic acids can inhibit neuraminidases.[8]
We report here the reaction of 3-aryl-2-sulfanylpropenoic acids with trichloroacetonitrile and other nitriles under various reaction conditions to give new 1,3-oxathiolanes, which were transformed into the corresponding thiazolidin-4-one derivatives
Summary
Abstract 3-Aryl-2-sulfanylpropenoic acids 1a-d react with trichloroacetonitrile under various reaction conditions to give different products. Reaction of 1a-d with trichloroacetonitrile in absolute ethanol and in the presence of few drops of triethylamine at room temperature affords 1,3oxathiolan-5-one derivatives 4a-d. Compounds 1a-d react with trichloroacetonitrile in primary alcohols under reflux to afford the corresponding 2-alkoxy-2-trichloromethylthiazolidin4-one derivatives 7a-l. Reaction of compounds 1a-d with trichloroacetonitrile or other nitriles 11a-c in refluxing glacial acetic acid gave 5-arylmethylene-2,4-thiazolidinediones 8a-d. The structures of all the newly synthesized products were confirmed based on elemental and spectral data, and a plausible mechanism is postulated to account for their formation. X-ray crystallography was carried out for the products 4a and 7b
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