Synthesis of dibenzothiazepine analogues by one-pot S-arylation and intramolecular cyclization of diaryl sulfides and evaluation of antibacterial properties

Dibenzothiazepine analogues containing lactam, amidine and imine moieties were prepared from 2-aminophenyl disulfides one-pot -arylation. The -arylation involved cleavage of an S-S bond of disulfides and S Ar reaction in aqueous ammonia solution of L-cysteine to afford diaryl sulfides. Dibenzothiaze...

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Veröffentlicht in:Heterocyclic communications 2018-08, Vol.24 (4), p.219-230
Hauptverfasser: Shimotori, Yasutaka, Hoshi, Masayuki, Murata, Mari, Ogawa, Narihito, Miyakoshi, Tetsuo, Kanamoto, Taisei
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Sprache:eng
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Zusammenfassung:Dibenzothiazepine analogues containing lactam, amidine and imine moieties were prepared from 2-aminophenyl disulfides one-pot -arylation. The -arylation involved cleavage of an S-S bond of disulfides and S Ar reaction in aqueous ammonia solution of L-cysteine to afford diaryl sulfides. Dibenzothiazepine analogues having lactam and amidine moieties were obtained by cyclization of the corresponding diaryl sulfides under acidic conditions. One-pot -arylation of 2-bromo-5-nitrobenzaldehyde gave dibenzothiazepine analogues with an imine moiety in one step through intramolecular cyclization. Compounds with antibacterial activities against and were obtained.
ISSN:0793-0283
2191-0197
DOI:10.1515/hc-2018-0099