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Cyclocondensation of Thioamides and Haloacetic Acid Derivatives Provides Only 4-Thiazolidinones; Isomeric 5-Thiazolidinones Were Not observed |
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| Authors: | Danylo Kaminskyy Andrzej K Gzella |
| Institution: | 1. Department of Pharmaceutical, Organic, and Bioorganic Chemistry , Danylo Halytsky Lviv National Medical University , Lviv , Ukraine;2. Department of Organic Chemistry , Poznan University of Medical Sciences , Poznań , Poland |
| Abstract: | Cycloaddition of intermediates formed from the nucleophilic addition of aryl isothiocyanate to acidic cyanomethylenes and α-halocarbonyl compounds gave only 4-thiazolidinones. 5-Thiazolidinones were not observed. Cyano-(4-oxo-3-phenylthiazolidin-2-ylidene)-acetic acid ethyl ester (1) and cyano-5-(4-methoxybenzylidene)-4-oxo-3-phenylthiazolidin-2-ylidene]-acetic acid ethyl ester (2a) also were shown to exhibit moderate antiviral activity. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] |
| Keywords: | Cyclocondensation 4-thiazolidinones 5-thiazolidinones X-ray |