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Synthesis of new amidino-substituted 2- aminothiophenoles: mild basic ring opening of benzothiazole (CROSBI ID 145042)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Racané, Livio ; Tralić-Kulenović, Vesna ; Mihalić, Zlatko ; Pavlović, Gordana ; Karminski-Zamola, Grace Synthesis of new amidino-substituted 2- aminothiophenoles: mild basic ring opening of benzothiazole // Tetrahedron, 64 (2008), 51; 11594-11602. doi: 10.1016/j.tet.2008.10.026

Podaci o odgovornosti

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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Podaci o izdanju

64 (51)

2008.

11594-11602

objavljeno

0040-4020

1464-5416

10.1016/j.tet.2008.10.026

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Kemija

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