Synthesis of Analogues of Natural Coumarins and Coumarinolignans

Abstract

3-Aryl-4H-coumarins with the 1,3-benzodioxol, 1,4-benzodioxane, and 1,5-benzodioxepane moieties were synthesized by modified methods. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2005, vol. 31, no. 3; see also http://www.maik.ru.

Synthesis of structural fragments of natural 3-phenoxycoumarins

“…According to method A, the appropriate salicylal dehyde (I)-(IV) phenoxyacetic acid (V) was con densed in the Perkin reaction [1]. In method B, start ing compounds were condensed in dimethylforma mide in the presence of trichloroacetic acid and acetic anhydride according to the Edgeworin synthesis pro cedure [3].…”

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Natural coumarin and phenoxycoumarin bioregu lators have a broad range of physiological activity and are a fertile field for chemical modifications [1].Traditionally, substituted and unsubstituted 3 phe noxycoumarins are synthesized using the Perkin reac tion [2], the Edgeworin synthesis procedure [3], the Kostanetsky-Robinson reaction, or modified versions of them [4].The most common method used to synthesize phe noxycoumarins containing O aryl substituents in the 3 position is the interaction of the appropriate alde hydes with phenoxyacetic acids and their functional derivatives. Compounds possessing antimicrobial [2], herbicidal, fungicidal, and insecticidal activity, as well as activity against dermatophytes [5], were identified during the study of biological activity.

Abstract-The synthesis of substituted and unsubstituted 3 phenoxycoumarins is described.

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“…Natural coumarin and phenoxycoumarin bioregu lators have a broad range of physiological activity and are a fertile field for chemical modifications [1].…”