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Nitroacetic Esters in the Regioselective Synthesis of Isoxazole-3,5-dicarboxylic Acid Derivatives. 2019
Alexander Yu Smirnov, and
Elvira R Zaitseva, and
Olga A Belozerova, and
Roman S Alekseyev, and
Nadezhda S Baleeva, and
Marina B Zagudaylova, and
Andrey A Mikhaylov, and
Mikhail S Baranov
Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia.
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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