On Regioselectivity of Aldol Condensation of Aromatic Aldehydes with Borate Complex of Acetylacetone
Kirkwood M. Land: 0000-0001-5951-9630
Print: 0039-7911, Electronic: 1532-2432
While cinnamoyl acetone 1 is obtained in good yield by a condensation of 3 molar excess of a borate complex of acetylacetone with benzaldehyde, products of Knoevenagel condensation 2 are predominantly obtained with furfural and 5-substituted furfurals. Cinnamoyl acetone 1 can be further condensed with furfural to form unsymmetrical curcuminoid 5. Compound 2a does not produce any new products under the same conditions. Compounds 3 and 5 are good inhibitors of growth of protozoan Trichomonas vaginalis.
Martichonok, V. V.,
Chiang, P. K.,
Dornbush, P. J.,
Land, K. M.
On Regioselectivity of Aldol Condensation of Aromatic Aldehydes with Borate Complex of Acetylacetone.
Synthetic Communications, 44(9), 1245–1250.