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ЖУРНАЛЫ // Mendeleev Communications // Архив

Mendeleev Commun., 2006, том 16, выпуск 6, страницы 318–319 (Mi mendc3641)

Эта публикация цитируется в 1 статье

Synthesis of quinolonecarboxylic acids from 1,3,5-trinitrobenzene

S. S. Vorob'ev, M. D. Dutov, O. V. Serushkina, M. A. Korolev, V. V. Kachala, Yu. A. Strelenko, S. A. Shevelev

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Аннотация: Products of nucleophilic substitution for one NO2 group in 1,3,5-trinitrobenzene were selectively reduced to 3-X-5-nitroanilines (X CF3CH2O, PhO, PhS), which were converted by condensation with EtOCHC(COOEt)2 to the respective enamines; acidcatalysed cyclization of the latter gives esters of X-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids. The cyclization direction depends on the substituent type: ortho (X CF3CH2O or PhO) or para (X PhS) with respect to NO2. N-Ethylation of these esters followed by hydrolysis gives the corresponding N-ethyl-5(7)-X-7(5)-nitroquinolinecarboxylic acids.

Язык публикации: английский

DOI: 10.1070/MC2006v016n06ABEH002390



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