Access to densely functionalized naphthalenes by organobase catalyzed domino reaction of 2-(2-formylaryl)acetophenones with nitroolefins

Abstract

A series of new functionalized naphthalene derivatives having carbonyl and NO2groups at C-1 and C-3 positions respectively have been prepared in good yields (63–75%) through a one-pot domino reaction of several 2-(2-formylaryl)acetophenone derivatives with a variety of aryl/heteroaryl-substituted 2-nitroolefins in EtOH as a green solvent at 75 °C under air using a catalytic amount of DABCO (30 mol %) as an inexpensive organocatalyst. This pot-economic process is friendly enough to retain several sensitive functionalities and displays a wide range of substrate scope. Furthermore, the high yielding synthesis of biologically attractive N-(3-naphthyl-substituted)pyrrole frameworks was established through our synthetic procedure. © 2016 Elsevier Ltd