Persulfate-nitrogen doped graphene mixture as an oxidant for the synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters and nitrite

Abstract

A series of 3-nitro-4-aryl-2H-chromen-2-ones in good yields have directly been obtained from aryl alkynoate esters and nitrite by employing a mixture of K₂S₂O₈-nitrogen doped graphene as an oxidant in a watery medium at room temperature. A plausible mechanism for the reaction is also reported. It reveals that the product is formed through a cascade of nitro radical addition, spirocyclization, and ester migration. When compared to known methods for the synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters, this protocol is environmentally friendly, sustainable, practical and energy efficient and does not use a harmful nitro source. Furthermore, nitrogen doped graphene used in this approach can be easily recovered and reused at least four times without losing its activity.