ChemInform Abstract: Unexpected Transformation of Thiazepines into Diazepines.

Abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Recyclization of 4,5-bis(aroyl)-2,3-dihydro-1H-pyrrole-2,3-diones by the action of aromatic amines

“…We previously reported on reactions of monocyclic 2,3-dihydro-1H-pyrrole-2,3-diones with aromatic amines, which resulted in the formation of addition products at the C 5 atom in the pyrrole ring, 5-arylamino-3-hydroxy-1H-pyrrole-2(5H)-ones [1][2][3]. By reaction of 4,5-bis(aroyl)-1-(4-methoxyphenyl)-2,3-dihydro-1H-pyrrole-2,3-diones Ia and Ib with p-anisidine at a molar ratio of 1 : 1 in anhydrous chloroform at room temperature (reaction time 8-10 h) we obtained (4Z)-5-aryl-[2-aryl-1-(4-methoxyphenylamino)-2-oxoethylidene]-5-hydroxy-1-(4-methoxyphenyl)pyrrolidine-2,3-diones IIIa and IIIb in good yields.…”

Five-membered 2,3-dioxoheterocycles: LXVII. Pyrroledione-pyrroledion recyclization of isopropyl 2-(1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)-2-oxoacetates under the action of arylamines. Crystal and molecular structure of (z)-isopropyl 2-hydroxy-4,5-dioxo-1-phenyl-3-[phenyl(phenylamino)-methylene]pyrrolidine-2-carboxylate

“…The crystal and molecular structure of (Z)-isopropyl 2-hydroxy-4,5-dioxo-1-phenyl-3-[phenyl(phenylamino)methylene]pyrrolidine-2-carboxylate was proved by XRD analysis.The reaction of 1-aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with arylamines was shown to result in the formation of the products of primary amino group addition to the carbon atom in the position 5 of pyrrolediones, substituted 5-arylamino-3-hydroxy-1H-pyrrol-2(5H)-ones [2,3].In extension of the research on the nucleophilic recyclization of 1H-pyrrole-2,3-diones we studied the reactions of the representatives of another class of monocyclic pyrrolediones, isopropyl 2-(1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)-2-oxoacetates IaIc [4] with primary amines IIa-IId.The reaction of compounds Ia-Ic with amines IIaIId in a ratio 1:1 performed by keeping the reagents solution in an anhydrous chloroform at room temperature over 8-10 h provided in good yield isopropyl 1-aryl-2-hydroxy-4,5-dioxo-3-[phenyl(arylamino)methylene]-pyrrolidine-2-carboxylates IIIa-IIIj. The structure of compound IIIa was proved by XRD analysis.…”

“…The reaction of 1-aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with arylamines was shown to result in the formation of the products of primary amino group addition to the carbon atom in the position 5 of pyrrolediones, substituted 5-arylamino-3-hydroxy-1H-pyrrol-2(5H)-ones [2,3].…”

Recyclization of isopropyl (1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)oxoacetates by the action of o-aminophenol

“…Reactions of 4-acyl-1H-pyrrole-2,3-diones with o-phenylenediamine and o-aminobenzenethiol involve successive attack by two nucleophilic centers of the reagents on the carbon atom in position 5 and carbonyl group in the acyl substituent on C 4 of the substrate to give substituted pyrrolobenzodiazepines [1] and pyrrolobenzothiazepines [2], respectively.…”