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

Authors

Val V. Martichonok, Pharmadyn, Inc.Follow
Peter K. Chiang, Pharmadyn, Inc.
Padraick J. Dornbush, University of the Pacific
Kirkwood M. Land, University of the PacificFollow

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.

Recommended Citation

Martichonok, V. V., Chiang, P. K., Dornbush, P. J., & Land, K. M. (1905). On Regioselectivity of Aldol Condensation of Aromatic Aldehydes with Borate Complex of Acetylacetone. Synthetic Communications, 44(9), 1245–1250. DOI: 10.1080/00397911.2013.850094
https://scholarlycommons.pacific.edu/cop-facarticles/796