Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols

1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-2-naphthols. It has been revealed that electron withdrawing groups on the aryl thiol promoted the yields and heterocycle substituents at the 3-position of the naphthalene core are tolerable by the reaction. This reaction can thus serve as a corner stone in the structural diversification of 3-heterocycle substituted 1-arylthio-2-naphthols as potential inhibitors of cytochrome P450.