The synthesis of 2,3,5-trisubstituted phenols

Abstract

Synthetic route to 2,3,5-trisubstituted phenols based on two-step [1+2+3] construction of the phenol backbone from 1-[(trimethylsilyl)methyl]-1H-1,2,3-benzotriazole, aliphatic or arylacetic acid chlorides and chalcones or α,β-unsaturated-γ-diketones was developed. 2,3,5-Trisubstituted phenols 8, 9a-e, 10a-d, 12a-e were successfully synthesized.

Domino Michael−Aldol Reactions on 1,4-Diarylbut-2-ene-1,4-diones with Methyl Acetoacetate Furnish Methyl 2-Aroyl-4- hydroxy-6-oxo-4-arylcyclohexane-1-carbox- ylate Derivatives

“…The cyclohexanecarboxylate 5 was treated with NaOMe in MeOH with the intention of effecting dehydration while keeping the ester moiety intact. However, surprisingly, this reaction furnished the known 3,5-disubstituted phenol 17 (Scheme ). In this transformation, loss of ester and water were taking place with concomitant dehydrogenative aromatization.…”