Neue Synthesen alkylaryl- und diaryl-disubstituierter Phenole und Salicylsäure-ethylester

Improved Syntheses of 3,5-Diaryl-Substituted Phenols

“…Significantly, we prepared the 3-(ortho-substituted-aryl)phenol 6g in 52% yield. This type of ortho-substituted 3,5-diarylphenol was previously unknown and specifically could not be prepared by the method of Eichinger et al 3 Our method thus allows access to a wider variety of phenols. Constants and NMR characteristics of phenols 6a-g are shown in Tables 1 and 2.…”

“…Even milder aromatization methods, e.g., oxidation by bromine, , did not guarantee improved yields or better isolation procedures. Tandem Michael addition/aldol condensation of 1-(2-oxopropyl)pyridinium chloride with chalcones forms cyclohexenones, which aromatize by the elimination of pyridinium chloride to give 3,5-diaryl-substituted phenols. , With the exception of 3-(4-nitrophenyl)-5-phenylphenol (82%), yields of 3,5-diarylphenols were poor to moderate (34−62%) via this method.…”

“…Although much less familiar than their alkyl-substituted analogues, aryl-substituted phenols have recently shown interesting potential for the preparation of “molecular harpoons” . Previous procedures for the syntheses of arylated phenols , are mostly of academic interest rather than solid preparative methods. Synthetic routes based on assembling the phenol backbone from “aliphatic building blocks” seem to be of most promise, generally involving intermediate aryl-substituted cyclohex-2-enones or 6-(ethoxycarbonyl)cyclohex-2-enones from the reaction of chalcones with carbonyl compounds carrying CH 2 C(O) or CH 2 C(O)CH 2 fragments…”

A Novel and Efficient Synthesis of [1,2,3]-Triazolyl Substituted Benzo[<i>c</i>]Coumarins and Evaluation of their Antimicrobial Activity

“…It is reported that reaction of α,β-unsaturated ketone with methyl ketone or ketone with active methylene group in the presence of sodium acetate results in a formation of 1,3,5-tri substituted benzene derivatives [42]. This novel reaction is utilized in the preparation of present compounds.…”

The synthesis of 2,3,5-trisubstituted phenols

“…5 Our recent study of [3+3] annulation reactions of 1-(benzotriazol-1-yl)propan-2-one with chalcones 6 gave an access to 3,5-diarylphenols advantageous as compared to the previously reported aromatization of cyclohexenones 7a,b and Michael addition/aldol condensation of 1-(2-oxopropyl)pyridiniums salts with chalcones. 8 No general method has previously been described for the preparation of meta-acylphenols, few of which are known. 9a-c We have now generalized our previous approach 6 to obtain 2,3,5-trisubstituted phenols 9a-e, 10a-d and 11c-d via stepwise [1+2+3] formation of the phenol backbone from "aliphatic" building blocks (Scheme 1).…”