One-pot efficient synthesis of novel fused pentacyclic indolopyridobenzimidazoles and pyridoimidazopyridoindoles from the reaction of pyranoindolones with 1,2-diaminobenzenes and 2,3-diaminopyridines

The synthesis of a number of novel, fully conjugated, planar pentacyclic 5H-indolo[3′,2′:4,5]pyrido[1,2-a][1,3]benzimidazoles (8) and 11H-pyrido[3″,2″:4′,5′]imidazo[1′,2′:1,6]pyrido[3,4-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.