Parallel Solid-Phase Synthesis of 2-Imino-4-oxo-1,3,5-triazino[1,2-<i>a</i>]benzimidazoles via Tandem Aza-Wittig/Heterocumulene-Mediated Annulation Reaction

Abstract

The parallel synthesis of a large number of 2-imino-4-oxo-1,3,5-triazino[1,2-a]benzimidazole derivatives via a solid-phase 1,3,5-triazino-annulation reaction is described. The solid-phase approach involves the in situ generation of iminophosphorane derivatives derived from resin-bound 2-aminobenzimidazoles employing Mitsunobu conditions. The subsequent Aza-Wittig reaction of the iminophosphoranes with isocyanates leads to highly reactive carbodiimides, which undergo an intramolecular heterocyclization reaction to form tetrasubstituted 2-imino-4-oxo-1,3,5-triazino[1,2-a]benzimidazoles in high yields (74-94%) and good purity (>80%).