Reactions of 4,6-dinitrobenzo[c]isoxazoles with nucleophiles

Autor:	Vasily V. Mezhnev, Vadim V. Kachala, Mikhail D. Dutov, Svyatoslav A. Shevelev
Rok vydání:	2010
Předmět:	Anthranil chemistry.chemical_compound chemistry Nucleophile Stereochemistry Nitro Nucleophilic substitution General Chemistry Phenols Isoxazole Ring (chemistry) Medicinal chemistry
Zdroj:	Russian Chemical Bulletin. 59:662-664
ISSN:	1573-9171 1066-5285
DOI:	10.1007/s11172-010-0128-x
Popis:	Reactions of nucleophiles with 3-R-4, 6-dinitrobenzo[c]isoxazoles (anthranils) were studied. Reactions of 4, 6-dinitroanthranil (R = H) with anionic O- and S-nucleophiles (phenols and benzenethiols in the presence of K2CO3) do not result in displacement of the nitro groups. The malonodinitrile anion (C-nucleophile) attacks the C(3) atom with opening of the isoxazole ring followed by recyclization into 2-amino-5,7-dinitroquinoline-3-carbonitrile N-oxide. The 5-NO2 group in the latter is smoothly replaced under the action of benzenethiol and 4-chlo-rophenol in the presence of K2CO3. In the case of 3-substituted anthranil (R = COCH3), one nitro group (4-NO2) is replaced under the action of benzenethiol and NaN3.
Databáze:	OpenAIRE
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