Nitroacetic Esters in the Regioselective Synthesis of Isoxazole-3,5-dicarboxylic Acid Derivatives
2019
Smirnov, Alexander Yu | Zaitseva, Elvira R. | Belozerova, Olga A. | Alekseyev, Roman S. | Baleeva, Nadezhda S. | Zagudaylova, Marina B. | Mikhaylov, Andrey A. | Baranov, Mikhail S.
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-6H-1,2-oxazine-3-carboxylates. In addition, the mechanism of the Dornow reaction was partially revised.
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