Polycyclic N-heterocyclic compounds. Part 61: A novel Truce–Smiles type rearrangement reaction of 4-(2-cyanovinyloxy)butanenitriles to give cycloalkeno[1,2- d]furo[2,3- b]pyridines

Abstract

The cycloalkeno[1,2- d]furo[2,3- b]pyridine skeleton was conveniently synthesized from fused 4-(2-cyanovinyloxy)butanenitriles in one step through sequential intramolecular Michael addition, β-elimination and intramolecular nucleophilic addition. This sequence thus consists of a novel Truce–Smiles type rearrangement followed by cyclization. The 5-amino derivatives were transformed further to lactams in good yields.