Journal
RSC ADVANCES
Volume 13, Issue 48, Pages 34299-34307Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ra05421g
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A simple and efficient approach was developed to synthesize multifunctional phenols via the 1,3-dianionic annulation of acetone. Different substituted ketones were used to obtain a variety of phenolic compounds. The structure of one compound was confirmed using the single-crystal X-ray approach.
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. A simple and efficient approach was developed via the 1,3-dianionic annulation of acetone to afford multifunctional phenols.
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