Nitroacetic Esters in the Regioselective Synthesis of Isoxazole-3,5-dicarboxylic Acid Derivatives.

Autor:	Smirnov AY; Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia., Zaitseva ER; Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia.; D. Mendeleev University of Chemical Technology of Russia , 9 Miusskaya Square , Moscow 125047 , Russia., Belozerova OA; Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia., Alekseyev RS; Department of Chemistry , M.V. Lomonosov Moscow State University , Moscow 119991 , Russia., Baleeva NS; Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia., Zagudaylova MB; Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia., Mikhaylov AA; Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia., Baranov MS; Institute of Bioorganic Chemistry , Russian Academy of Sciences , Miklukho-Maklaya 16/10 , Moscow 117997 , Russia.; Pirogov Russian National Research Medical University , Ostrovitianov 1 , Moscow 117997 , Russia.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2019 Dec 06; Vol. 84 (23), pp. 15417-15428. Date of Electronic Publication: 2019 Nov 18.
DOI:	10.1021/acs.joc.9b02427
Abstrakt:	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 H -1,2-oxazine-3-carboxylates. In addition, the mechanism of the Dornow reaction was partially revised.
Databáze:	MEDLINE
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