Synthesis of new amidino-substituted 2-aminothiophenoles: mild basic ring opening of benzothiazole

Racané, Livio; Tralić-Kulenović, Vesna; Mihalić, Zlatko; Pavlović, Gordana; Karminski-Zamola, Grace

doi:10.1016/j.tet.2008.10.026

Pregled bibliografske jedinice broj: 368636

Synthesis of new amidino-substituted 2- aminothiophenoles: mild basic ring opening of benzothiazole

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 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 368636 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Synthesis of new amidino-substituted 2- aminothiophenoles: mild basic ring opening of benzothiazole

Autori
Racané, Livio ; Tralić-Kulenović, Vesna ; Mihalić, Zlatko ; Pavlović, Gordana ; Karminski-Zamola, Grace

Izvornik
Tetrahedron (0040-4020) 64 (2008), 51; 11594-11602

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
benzothiazole ; amidine ; Pinner reaction ; disulfide ; thiolate

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA

Projekti:
MZOS-117-0000000-3283 - Istraživanje novih višenamjenskih bojila i optičkih bjelila (Racane, Livio, MZOS ) ( CroRIS)
MZOS-119-1191342-1339 - Molekulsko modeliranje strukture i reaktivnosti organskih spojeva (Mihalić, Zlatko, MZOS ) ( CroRIS)
MZOS-125-0982464-1356 - Novi heterocikli kao antitumorski i antivirusni (pametni) lijekovi (Hranjec, Marijana, MZOS ) ( CroRIS)

Ustanove:
Tekstilno-tehnološki fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Profili:

Vesna Tralić-Kulenović (autor)