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One-pot efficient synthesis of novel fused pentacyclic indolopyridobenzimidazoles and pyridoimidazopyridoindoles from the reaction of pyranoindolones with 1,2-diaminobenzenes and 2,3-diaminopyridines
Authors:Despina Livadiotou  Anna Maria Fadel  Constantinos A Tsoleridis  Julia Stephanidou-Stephanatou
Institution:Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
Abstract:The synthesis of a number of novel, fully conjugated, planar pentacyclic 5H-indolo3′,2′:4,5]pyrido1,2-a]1,3]benzimidazoles (8) and 11H-pyrido3″,2″:4′,5′]imidazo1′,2′:1,6]pyrido3,4-b]indoles (12) by a one-pot reaction of pyranoindolones with substituted o-phenylenediamines or 2,3-diaminopyridines is described. In the case of 2,3-diaminopyridines the reaction proceeds regioselectively affording only regioisomers 12. Structural assignments of the new compounds as well as complete assignment of 1H and 13C NMR signals were based on the analysis of their 1H and 13C NMR (1D and 2D), IR, MS and elemental analysis data. Plausible mechanisms are proposed.
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