Synthesis and electrochemical evaluation of substituted imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine scaffolds
In: Magdi E.A. Zaki, 2012-06-01
Online
academicJournal
Zugriff:
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.
Fundação para a Ciência e a Tecnologia (FCT)
Titel: |
Synthesis and electrochemical evaluation of substituted imidazo[4,5-d]pyrrolo[3,2-f][1,3] diazepine scaffolds
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Autor/in / Beteiligte Person: | Zaki, M. ; Bettencourt, Ana Paula ; Fernandes, Francisco Manuel Carvalho Pinto ; Proença, M. Fernanda R. P. ; Universidade do Minho |
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Zeitschrift: | Magdi E.A. Zaki, 2012-06-01 |
Veröffentlichung: | Elsevier, 2012 |
Medientyp: | academicJournal |
DOI: | 10.1016/j.tet.2012.04.030 |
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