1,3-Dianionic annulation of ketones with ketene dithioacetal: a modified route to 3-aryl/cyclopropyl-5-thiomethyl-phenols and 1-(methylthio)-9,10-dihydrophenanthren-3-ols

Abstract

A simple and efficient base-mediated [3 + 3] cyclization of 1,3-dianionic ketones with 3,3-bis(methylthio)-1-arylprop-2-en-1-ones was developed to afford 3-hydroxy-biaryls, hydroxy-xylenes, and hydroxy-teraryls. Various tri- and tetra-substituted phenols were prepared from different symmetric and asymmetric ketones. The reaction of 2-(bis(methylthio)methylene)-3,4-dihydronaphthalen-1(2H)-ones with different ketones provided 1-(methylthio)-9,10-dihydrophenanthren-3-ols in very good yield. The scope of the reaction was further extended by the synthesis of cyclopropyl-functionalized phenols. One of the compounds was crystallized, and its structure was confirmed using the single-crystal X-ray approach.