An efficient and high-yielding strategy to prepare "unsymmetrical" 4-aryl-isoxazol-3,5-dicarboxylic acid derivatives from nitroacetic esters and aromatic aldehydes has been developed. The strategy is based on the isolation and usage of the previously missed intermediate of the Dornow reaction-5-hydroxy-6-oxo-4-aryl-6-1,2-oxazine-3-carboxylates. In addition, the mechanism of the Dornow reaction was partially revised.
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| http://dx.doi.org/10.1021/acs.joc.9b02427 | DOI Listing |
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