SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED ISOXAZOLES AS INTERMEDIATES FOR BENT-CORE MESOGENS
Keywords:
liquid crystals, bent-core, ring closure, isoxazoleAbstract
3,5-Disubstituted isoxazoles have been designed and synthesized to be used as central units for bent-core mesogens. The substituents at position 3 of the isoxazole ring are either hydroxymethyl or carboxyl, while alkenyl-terminated substituents have been inserted at position 5. A multi-step reaction sequence comprising the O-alkylation of 4-hydroxyacetophenone with the suitable alkenyl halide, the Claisen-type condensation with diethyl oxalate and the cyclization to isoxazole led to the isoxazole esters as key intermediates, which were subsequently reduced and hydrolyzed to the corresponding isoxazol-3-ylmethanols and isoxazole-3-carboxilic acids, respectively.
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