Synthesis of Novel Bioactive Candidates 4-Aryl-1H-indeno[1,2-d]pyrimidine-2,5-diones Using {[HMIM]C(NO₂)₃} as a Dual Rule Ionic Liquid Catalyst: An Experimental and Theoretical Evaluation of Their Corresponding Antioxidant Activities

Abstract

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 anti-oxidant activities of the target molecules were also checked out.

Graphical Abstract

Keywords:

• Anomeric based oxidation
• antioxidant activity
• DPPH^•
• ionic liquid catalyst
• multi-component reactions
• new substituted 4-phenyl-1H-indeno[1,2-d]pyrimidine-2,5-diones

Acknowledgment

The authors are thankful to Prof. Zolfigol for providing the ionic liquid catalyst.

Disclosure statement

The authors declare that they have no competing interests.

Additional information

Funding

The authors gratefully acknowledge the financial support for this work from the Bu-Ali Sina University, Hamedan, Iran.