An efficient one-pot multi-component reaction of 1,3-indanedione, aryl aldehydes and urea leading to new series of 4-aryl-1H-indeno[1,2-d] pyrimidine-2,5-diones in the presence of a catalytic amount of 1-methylimidazolium trinitromethanide {[HMIM]C(NO2)3}, as a nano ionic liquid, at ambient temperature under solvent-free conditions is reported. Advantages of the present protocol are the operationally simple and simple work-up, good to excellent yields, short reaction times, dual catalytic activity and reusability of the described catalyst. Finally, considering the role of oxidative stress in the progress of many ailments, the synthesized indenopyrimidine derivatives was screened for their corresponding anti-oxidant activities. Theoretical investigation of antioxidant activities of the target molecules were also checked out.