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- Title
3-Aryl-2-sulfanylpropenoic acids as precursors for some novel (Z)-5-substituted-2-alkoxy-2-trichloromethyl-4-thiazolidinones.
- Authors
Metwally, Nadia Hanafy
- Abstract
3-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.
- Subjects
ACRYLIC acid; AROMATIC compounds; CHEMICAL precursors; SUBSTITUTION reactions; ALKOXY compounds; TRICHLOROMETHYL group
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2011, p254
- ISSN
1551-7004
- Publication type
Article