Preparation of 2,2'-Dihydroxytriphenylmethanes Using Metal Phenolates with Aromatic Aldehydes.

Abstract

The reactions of oxophilic metal phenolates having electron-donating substituents (1a-c) with aromatic aldehydes (2, 3) were selectively condensed at the ortho-position of the starting phenol to afford 2,2'-dihydroxytriphenylmethanes (8-11). This method was also applicable to the preparation of bisphenols (12-17) starting with naphthaldehydes (4, 5) and pyridinecarboxaldehydes (6, 7), but in low yields. In the case of these aldehydes (4-7), satisfactory yields could be obtained by sonication.

Synthesis of 2,2'-Dihydroxybisphenols and Antiviral Activity of Some Bisphenol Derivatives.

“…4) The results are summarized in Antiviral activities of some 2,2Ј-dihydroxybisphenols (5b and 6-9 4) ) and 4,4Ј-dihydroxybisphenol (10) 4) (see Fig. 1) were examined by plaque reduction assay as described by Schinazi et al 5) The results (EC 50 : 50% effective concentration) of six compounds by this assay are summarized in Table 5.…”

“…The synthetic methodologies have already been reported. 4) The results of molecular modification of the prototype 10 and biological screening will be described elsewhere.…”

“…4) For the synthetic application of the procedure and biological evaluation of the related compounds, we attempted to synthesize diphenylmethane-type 2,2Ј-dihydroxybisphenol derivatives with some aliphatic aldehydes as starting material. In this paper, we wish to report the syntheses of some 2,2Ј-dihydroxybisphenols for lead compounds and also to communicate significant antiviral activities of some of the related compounds by the plaque reduction assay.…”

Synthesis and Antiviral Activities of Some 4,4'-Dihydroxytriphenylmethanes

“…1) with a substituted aryl group were synthesized from phenol or a halogenated phenol and the selected aromatic aldehyde with Brønsted acid or Lewis acid by a slightly modified procedure reported previously. 1,4,5) As mentioned before, 1,5) the reactions proceed in a C-para regiospecific manner via the bisarylation of aldehyde. These methods employed various acids, including trifluoroacetic acid (TFA) Table 1.…”

“…Using TFA as the catalyst for the preparation of the target compounds is conventional and usually gives good to moderate results. 6) The physical data for compounds (1)(2)(3) are summarized in Table 2. NMR-spectroscopic analyses confirmed the symmetrical structure of the target compounds (1b, 2a-d) ( Table 1).…”