Reaction of Isoeugenol with Formaldehyde in Basic Medium: Formation of trans-4-(4-Hydroxy-3-hydroxymethyl-5-methoxy)-5-methyl-1,3-dioxane and its Transformation into the Tricyclo[5.2.2.02,6]undecane System†

Abstract

Formation of the title compound 3, via an unusual Prins-type reaction on isoeugenol with formaldehyde in alkaline medium, and its conversion into a tricyclo[5.2.2.0 2,6 ]undecane system 4 is described.

Comparative Study on the Antioxidant and Biological Activities of Carvacrol, Thymol, and Eugenol Derivatives

“…All derivatives have no strong odor as their parent compounds. Compounds 3 and 4 were previously synthesized , according to a similar method, whereas compound 2 was not synthesized before.…”

“…Chemical modifications, such as introducing polar hydroxymethyl moiety into phenol structures, can change antioxidant activity in comparison with the starting compounds . Hydroxymethylation reactions (nucleophilic addition to the carbonyl group) can be catalyzed by either acids or bases, and electrophilic aromatic substitution reaction of the newly formed hydroxymethylphenol with residual phenol can yield methylenediphenols – . The antioxidant properties of prepared derivatives were evaluated, for the first time, by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and Rancimat methods, as well as their antibacterial, antiyeast, and antiproliferative activities and compared to those of the parent compounds.…”

A Convergent Total Synthesis of the Biologically Active Benzo­furans Ailanthoidol, Egonol and Homoegonol from Biomass-Derived­ Eugenol

“…Thus, eugenol (7) was reacted with formalin solution in a basic medium (NaOH) to produce the desired allylic alcohol 6 in 85% yield (Scheme 3). 24 Treatment of 6 with triphenylphosphonium bromide in acetonitrile, as reported by Hamanaka and co-workers, 25 gave phosphonium salt 5 in 89% yield. The latter salt was used in the next step without further purification.…”

Synthesis and Evaluation of Marine-Inspired Compounds Result in Hybrids with Antitrypanosomal and Antileishmanial Activities

“…To obtain 2, eugenol (1) was subjected to O-alkylation with propargyl bromide in basic medium, according to a procedure described before [19]. The azide (4) was synthesized in three steps, namely by a hydroxymethylation reaction of eugenol (1) with formaldehyde in basic medium [20], followed by chlorination of the alcoholic intermediate (3) with thionyl chloride and one-pot nucleophilic substitution with sodium azide. Intermediate 4 formation was confirmed by NMR, in which a singlet relative to methylene protons alpha to the azido group could be observed at 4.37 ppm.…”