Notes. A Seven-Membered Heterocycle from o-Aminobenzenethiol and Chalcone

Syntheses of potentially bioactive [1,2,4]oxadiazolo[5,4‐d]benzothiazepines by 1,3‐dipolar cycloaddition

“…2a-2l were subsequently reacted with o-aminobenzenthiol in MeOH/AcOH to give the desired 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines, 3a-3l. The formation of 3 may proceeded via two steps [30,31]. In the first step, nucleophilic attack by the sulfhydryl electrons of 2-aminobenzenethiol takes place on the activated b-carbon atom of the a, b-unsaturated carbonyl compounds to give Michael-adduct type intermediates, which simultaneously undergo dehydrative cyclization to give final products in the second step.…”

Synthesis and structure characterization of new [1,2,4]triazolo[5,4‐d][1,5]benzothiazepine derivatives through 1,3‐dipolar cycloaddition reaction

“…Chalcones 2 (6 mmol) and o-aminobenzenthiol (6 mmol) were dissolved in 25 mL hot methanol [14]. After the mixture had cooled to room temperature and piperidine (five drops) was added, yellow solid appeared in 0.5 h, then a little methanol was added and the slurry heated until all material dissolved.…”

Synthesis of heterocyclic compounds by the reactions of exocyclic α,β‐unsaturated ketones

“…Numerous 2,4-disubstituted 2,3-dihydro-1,5-bezothiazepines have been synthesized by the reaction of α,β-enones and 2-aminothiophenol [2,5,[138][139][140][141][142][143][144][145]. Prior to our own studies, synthesis of tetracyclic benzothiazepines obtained by the same reaction of the related exocyclic α,β-unsaturated ketones was mentioned in the literature only in one case [140].…”