Synthesis of allylic thiocyanates and novel 1,3-thiazin-4-ones from 2-(bromomethyl)alkenoates and S-nucleophiles in aqueous medium |
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Authors: | Marcus M Sá Luciano Fernandes Misael Ferreira Adailton J Bortoluzzi |
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Institution: | Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil |
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Abstract: | Allylic thiocyanates and novel heterocycles containing the 1,3-thiazin-4-one core are easily obtained in high yields and mild conditions by nucleophilic displacement of 2-(bromomethyl)alkenoates (derived from Morita-Baylis-Hillman adducts) with sulphur-centred nucleophiles in aqueous acetone at 25 °C. Treatment of allylic bromides with NaSCN gave the corresponding (Z)-2-(thiocyanomethyl)alkenoates, while the reaction with thiourea followed by a basic work-up selectively produced (5Z)-2-amino-5-arylidene-1,3-thiazin-4-ones. The structural assignments were confirmed by X-ray diffraction analysis. |
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Keywords: | Allylic thiocyanate 1 3-Thiazinone 2-(Bromomethyl)alkenoate S-Nucleophiles Aqueous solvent |
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