On Regioselectivity of Aldol Condensation of Aromatic Aldehydes with Borate Complex of Acetylacetone

ORCID

Kirkwood M. Land: 0000-0001-5951-9630

Document Type

Article

Publication Title

Synthetic Communications

Department

Biological Sciences

ISSN

Print: 0039-7911, Electronic: 1532-2432

Volume

44

Issue

9

DOI

10.1080/00397911.2013.850094

First Page

1245

Last Page

1250

Publication Date

7-6-1905

Abstract

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.

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