Synthesis of new amidino-substituted 2- aminothiophenoles: mild basic ring opening of benzothiazole (CROSBI ID 145042)
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Racané, Livio ; Tralić-Kulenović, Vesna ; Mihalić, Zlatko ; Pavlović, Gordana ; Karminski-Zamola, Grace
engleski
Synthesis of new amidino-substituted 2- aminothiophenoles: mild basic ring opening of benzothiazole
The efficient synthesis of new amidino, N- isopropylamidino, 2-imidazolinyl substituted benzothiazoles and 2-aminothiophenoles by the Pinner reaction is described. The novel ring opening of benzothiazole with ammonia and ethylenediamine was found, and a plausible reaction mechanism proposed. The ring opening with ethylenediamine is selective and applicable to compounds bearing hydrolytically and amonolytically unstable substituents. Different amidinosubstituted 2- aminothiophenoles were isolated in zwitterionic and disulfide form and their structures were determined by X-ray crystal structure analysis.
benzothiazole ; amidine ; Pinner reaction ; disulfide ; thiolate
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