ChemInform Abstract: Preparation of Benzothieno(2,3‐f)‐1,4‐oxazepin‐ and ‐thiazepin‐5(2H)‐ ones and of Benzothieno(3,2‐e)‐1,4‐diazepin‐5‐ones.

Abstract

Preparation of Benzothieno(2,3-f )-1,4-oxazepin-and -thiazepin-5(2H)-ones and of Benzothieno(3,2-e)-1,4-diazepin-5-ones. -With a view to testing their potential biological activities title compounds such as (II), (VII), (XI), and (XIV), which are analogues of the antiinflammatory agent PD 144795, are synthesized. -(KHATANA, S. S.; BOSCHELLI, D. H.; KRAMER, J. B.; CONNOR, D. T.; BARTH, H.; STOSS, P.; J.

Synthesis and Structure−Activity Relationships of Benzothienothiazepinone Inhibitors of Protein Kinase D

“…Thionyl chloride-mediated Higa cyclization of acid 4 provided the benzo[ b ]thiophene acid chloride, which was subsequently converted to methyl ester 5 . Treatment of 5 with cysteamine hydrochloride in the presence of DBU resulted in formation of the desired benzothienothiazepinone core . Deprotection of the aryl benzyl ether with boron tribromide provided kb-NB142-70 in good yield, and O -methylation of kb-NB142-70 with methyliodide led to kb-NB165-09.…”

“…26 Debenzylation by transfer hydrogenation led to the phenol kb-NB123-57. 27 Benzothienothiazepinones kb-NB142-70 and kb-NB165-09 were synthesized according to a literature protocol 28,29 beginning with benzyl protection of commercially available 3-hydroxycinnamic acid (Scheme 2). Thionyl chloridemediated Higa cyclization of acid 4 provided the benzo-[b]thiophene acid chloride, which was subsequently converted to methyl ester 5.…”

“…Treatment of 5 with cysteamine hydrochloride in the presence of DBU resulted in formation of the desired benzothienothiazepinone core. 29 Deprotection of the aryl benzyl ether with boron tribromide provided kb-NB142-70 in good yield, and O-methylation of kb-NB142-70 with methyliodide led to kb-NB165-09.…”