A highly efficient [3+2] cyclization between 4-aminopyridinones and acenaphthenequinone: Access to novel acenaph-tho[1′,2':4,5]pyrrolo[3,2-c]pyridin-11-ones

Abstract

Direct and metal-free access to poly-substituted acenaphtho[1′,2':4,5]pyrrolo[3,2-c]pyridin-11-one and its analogs was established through a simple one-pot reaction using enaminones and acenaphthylene-1,2-dione as basic substrates. The reaction allows the formation of C–N and C–C bonds accompanied by multiple bond cleavage in the presence of acetic acid. The approach features atomic economy, broad substrate scope, efficient and metal-free reaction conditions, inexpensive and readily available starting materials and easy operation, making the strategy highly attractive. Importantly, the new acenaphtho[1′,2':4,5]pyrrolo[3,2-c]pyridin-11-ones with hydroxyl substituents could be further functionalized, affording access to molecular complexity and diversity.