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Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

[Image: see text] A green and optimized protocol has been developed for the preparation of symmetric 1,7-bis(aryl)-1,6-heptadiene-3,5-diones and asymmetric 2-aryl-6-arylidenecyclohexanones with modified substrate scope and good functional group tolerance. Syntheses proceed smoothly under solvent-fre...

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Detalles Bibliográficos
Autores principales: Stepanova, Valeria A., Guerrero, Andres, Schull, Cullen, Christensen, Joshua, Trudeau, Claire, Cook, Joshua, Wolmutt, Kyle, Blochwitz, Jordan, Ismail, Abdelrahman, West, Joseph K., Wheaton, Amelia M., Guzei, Ilia A., Yao, Bin, Kubatova, Alena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8892666/
https://www.ncbi.nlm.nih.gov/pubmed/35252716
http://dx.doi.org/10.1021/acsomega.1c07006
Descripción
Sumario:[Image: see text] A green and optimized protocol has been developed for the preparation of symmetric 1,7-bis(aryl)-1,6-heptadiene-3,5-diones and asymmetric 2-aryl-6-arylidenecyclohexanones with modified substrate scope and good functional group tolerance. Syntheses proceed smoothly under solvent-free conditions, providing moderate to excellent product yields with a minimal workup procedure. Control experiments, spectroscopic, and computational studies support a mechanism involving the boron-assisted in situ generation of imine intermediates. Crystal structures of three curcuminoids and isolated mechanistic intermediates are reported. The data provide insight for the further development of solvent-free protocols toward diverse curcumin derivatives in the fields of pharmaceutical and synthetic chemistries.