ChemInform Abstract: OXAZEPINES AND THIAZEPINES, III. SYNTHESIS OF 2,3‐DIHYDRO‐2,4‐DIPHENYL‐1,5‐BENZOTHIAZEPINES BY THE REACTION OF 2‐AMINOTHIOPHENOL WITH CHALCONES SUBSTITUTED IN RING A

Abstract

Die Reaktion der Aminothiophenole (I) mit den Chalkonen (II), (IV) bzw. (VI) liefert je nach dem Substituenten in Ring Adie Propiophenone (III), sowie die Thiazepine (V) bzw. (VII).Erhitzen von (III) in methanolischer Lösung und in Gegenwart katalytischer Mengen Essigsäure ergibt die Thiazepine (VIII).

Solvent‐Free Synthesis of 1,5‐Benzothiazepines and Benzodiazepines on Inorganic Supports

“…In the reaction of o-aminothiophenol with chalcones in refluxing toluene, from chalcones with electron-donating substituents such as methyl and methoxy group, only b-phenyl-b-(2-aminophenylmercapto)-propiophenones were formed, whereas from chalcones with electron-withdrawing substituents such as nitro group, only 1,5-benzothiazepines were formed. [16] In contrast, the reaction using silica gel under solvent-free conditions gave only 1,5-benzothiazepines in good yield independent of the chalcone substituents, with the exception of nitro and hydroxy groups. In the case of chalcones having nitro and hydroxy groups, the yields were lower than that of chalcones with the other substituents.…”

“…Chalcone reacts with o-aminothiophenol in refluxing toluene to afford the adduct, b-phenyl-b-(2-aminophenylmercapto)propiophenone, which could be converted to 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine by cyclization in the presence of an acid catalyst. [16] In contrast, the reaction of chalcone with o-aminothiophenol in the presence of silica gel was carried out at 808C under solvent-free conditions to obtain 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine in one-step.…”

“…[15] 1,5-Benzothiazepines have generally been synthesized by the reaction of o-aminothiophenol with a,b-unsaturated ketones. [16] 1,5-benzothiazepines have also been synthesized from oaminothiophenol, v-bromoacetophenones and aromatic aldehydes, [17] and by the reaction of a,b-unsaturated ketones with bis(2-nitrophenyl)disulfide by use of TiCl 4 /Sm [18] has been reported. There are few reports on the use of inorganic solid supports such as alumina, silica gel and clay for the synthesis of 1,5-benzodiazepines and benzothiazepines under solvent-free condition.…”

Application of Screening Methods, Shape Signatures and Engineered Biosensors in Early Drug Discovery Process

“…The two compounds I and J chosen for this test were dissolved in a mixture of 10% DMSO and 90% ethanol to form a 1 mM stock solution. Chemical names of compound I and J are 3-(2-aminophenyl) sulfanyl-1-(4-chlorophenyl)-3-phenyl-propan-1-one and 3-(2-aminophenyl)sulfanyl-3-(4-bromophenyl)-1-phenyl-propan-1-one, respectively (34,35). The stock solutions of compounds I and J were diluted to 25 μM for the ELISA assay.…”