Combinatorial synthesis of fused tetracyclic heterocycles containing [1,6]naphthyridine derivatives under catalyst free conditions

A three-component reaction between an aromatic aldehyde, an amine, and tert-butyl 2,4-dioxopiperidine-1-carboxylate in EtOH at refluxing temperature gave fused tetracyclic heterocycles in high yields. The amines include 1H-indazol-5-amine, 1H-indazol-6-amine, 1H-indol-5-amine, and 1H-benzo[d]imidazol-5-amine, giving 11-aryl-3H-indazolo[5,4-b][1,6] naphthyridine, 11-aryl-1H-indazolo[6,7-b][1,6]naphthyridine, 11-aryl-3H-indolo[5,4-b][1,6]naph-thyridine, and 11-aryl-3H-imidazo[4',5':3,4]benzo[1,2-b][1,6]naphthyridine derivatives, respectively.