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TitleSynthesis and electrochemical evaluation of substituted imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine scaffolds
Author(s)Zaki, M.
Bettencourt, Ana Paula
Fernandes, Francisco Manuel Carvalho Pinto
Proença, M. Fernanda R. P.
KeywordsCyanoformimidoyl imidazole
Cyclic voltammetry
Reduction potential
Issue dateJun-2012
CitationMagdi E.A. Zaki, A. Paula Bettencourt, Francisco M. Fernandes, M. Fernanda Proença, Synthesis and electrochemical evaluation of substituted imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine scaffolds, Tetrahedron, Volume 68, Issue 24, 17 June 2012, Pages 4628-4634, ISSN 0040-4020, 10.1016/j.tet.2012.04.030.
Abstract(s)Substituted 4-(2,5-dihydro-1H-pyrrol-3-yl)-1H-imidazoles were prepared from 5-amino-1-aryl-4-cyanoformimidoylimidazoles and cyanoacetamide, under mild experimental conditions. The pyrrolyl-imidazoles were cyclized to the corresponding 7,8-dihydroimidazo[4,5-b]pyrrolo[3,4-d]pyridines by reflux in ethanol, with catalysis by DBU. The same pyrrolyl-imidazoles were reacted with orthoesters, at room temperature and in the presence of sulfuric acid, to generate 3,7-dihydro-8H-imidazo[4,5-d]pyrrolo[3,2-f]diazepines in very good yield. Electrochemical studies of the imidazo[4,5-d]pyrrolo[3,2-f][1,3]diazepine derivatives were carried out. The reduction potential of 7-ethyl-3-(4-methoxyphenyl)-8-oxo-7,8-dihydro-3H-imidazo[4,5-d]pyrrolo[3,2-f][1,3]diazepine-9-carbonitrile was in the adequate range for presenting bioreduction properties.
Publisher versionThe original publication is available at
AccessRestricted access (UMinho)
Appears in Collections:CDQuim - Artigos (Papers)

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