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Dibenzothiazepine analogues containing lactam, amidine and imine moieties were prepared from 2-aminophenyl disulfides via one-pot S-arylation. The S-arylation involved cleavage of an S-S bond of disulfides and SNAr 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 S-arylation of 2-bromo-5-nitrobenzaldehyde gave dibenzothiazepine analogues with an imine moiety in one step through intramolecular cyclization. Compounds with antibacterial activities against Staphylococcus aureus and Escherichia coli were obtained. [ABSTRACT FROM AUTHOR]