Synthesis of 4,5-dihydrothiazole derivatives by the reaction of perfluoro-2-methylpent-2-en-3-yl isothiocyanate with ambident N,O- and N,S-nucleophiles |
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| Authors: | Rogoza A. V. Furin G. G. Gatilov Yu. V. Bagryanskaya I. Yu. |
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| Affiliation: | (1) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent"eva, 630090 Novosibirsk, Russian Federation |
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| Abstract: | The reactions of perfluoro-2-methylpent-2-en-3-yl isothiocyanate with ambident N,O- and N,S-nucleophiles (thiazole-2-thione, pyridine-2-thione, 2-hydroxypyridine, benzothiazole-2-thione, benzoxazole-2-thione, 3,4,5,6-tetrahydropyrimidine-2-thione) in the presence of triethylamine yield only 2-N-substituted 4,5-dihydrothiazole derivatives. The molecular structures of three products were determined by X-ray diffraction analysis. The reaction pathways are discussed. |
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| Keywords: | nucleophilic substitution heterocyclization perfluoro-2-methylpent-2-en-3-yl isothiocyanate heterocumulenes regioselectivity NMR spectroscopy X-ray diffraction analysis |
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