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Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids
Valeria A Stepanova1, Andres Guerrero1, Cullen Schull1
1Department of Chemistry and Biochemistry, University of Wisconsin La Crosse, 1725 State Street, La Crosse, Wisconsin 54601, United States.
ACS Omega
|March 7, 2022
Summary
A new green synthesis method prepares curcuminoids and cyclohexanones efficiently under solvent-free conditions. This optimized protocol offers good yields and functional group tolerance for diverse chemical applications.
Area of Science:
- Organic Chemistry
- Green Chemistry
- Synthetic Chemistry
Background:
- Curcuminoids and cyclohexanones are valuable scaffolds in medicinal and synthetic chemistry.
- Existing synthetic methods often involve harsh conditions, solvents, and limited functional group tolerance.
Purpose of the Study:
- To develop a green, optimized, and efficient protocol for synthesizing symmetric 1,7-bis(aryl)-1,6-heptadiene-3,5-diones and asymmetric 2-aryl-6-arylidenecyclohexanones.
- To explore the scope and functional group tolerance of the new synthetic method.
- To elucidate the reaction mechanism using control experiments, spectroscopic, and computational studies.
Main Methods:
- Solvent-free synthesis conditions.
- Boron-assisted in situ generation of imine intermediates.
- Spectroscopic and computational analyses for mechanistic elucidation.
- X-ray crystallography for structural determination.
Main Results:
- Successful synthesis of symmetric 1,7-bis(aryl)-1,6-heptadiene-3,5-diones and asymmetric 2-aryl-6-arylidenecyclohexanones.
- Moderate to excellent product yields achieved under optimized conditions.
- Demonstrated good functional group tolerance and modified substrate scope.
- Proposed a reaction mechanism involving boron-assisted imine formation.
- Reported crystal structures of key compounds and intermediates.
Conclusions:
- The developed green protocol offers an efficient and environmentally friendly route to diverse curcumin derivatives.
- The mechanistic insights provide a foundation for further development of solvent-free synthetic strategies.
- This work contributes to advancing the synthesis of valuable compounds for pharmaceutical and synthetic chemistry applications.
