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

Sergei Sergeyevich Vorob'ev 1
Sergei Sergeyevich Vorob'ev
, 
Mikhail Dmitrievich Dutov 1
Mikhail Dmitrievich Dutov
, 
Ol'ga Victorovna Serushkina 1
Ol'ga Victorovna Serushkina
, 
Maksim Aleksandrovich Korolev 1
Maksim Aleksandrovich Korolev
, 
Vadim Vadimovich Kachala 1
Vadim Vadimovich Kachala
, 
Yurii Andreevich Strelenko 1
Yurii Andreevich Strelenko
, 
Svyatoslav Arkad'evich Shevelev 1
Svyatoslav Arkad'evich Shevelev
10.1070/MC2006v016n06ABEH002390
Published 2006-12-06
Communication , Volume 16, Issue 6, 318-319
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Vorob'ev S. S. et al. Synthesis of quinolonecarboxylic acids from 1,3,5-trinitrobenzene // Mendeleev Communications. 2006. Vol. 16. No. 6. pp. 318-319.
GOST all authors (up to 50) Copy
Vorob'ev S. S., Dutov M. D., Serushkina O. V., Korolev M. A., Kachala V. V., Strelenko Y. A., Shevelev S. A. Synthesis of quinolonecarboxylic acids from 1,3,5-trinitrobenzene // Mendeleev Communications. 2006. Vol. 16. No. 6. pp. 318-319.
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TY - JOUR
DO - 10.1070/MC2006v016n06ABEH002390
UR - https://mendcomm.colab.ws/publications/10.1070/MC2006v016n06ABEH002390
TI - Synthesis of quinolonecarboxylic acids from 1,3,5-trinitrobenzene
T2 - Mendeleev Communications
AU - Vorob'ev, Sergei Sergeyevich
AU - Dutov, Mikhail Dmitrievich
AU - Serushkina, Ol'ga Victorovna
AU - Korolev, Maksim Aleksandrovich
AU - Kachala, Vadim Vadimovich
AU - Strelenko, Yurii Andreevich
AU - Shevelev, Svyatoslav Arkad'evich
PY - 2006
DA - 2006/12/06
PB - Mendeleev Communications
SP - 318-319
IS - 6
VL - 16
ER -
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@article{2006_Vorob'ev,
author = {Sergei Sergeyevich Vorob'ev and Mikhail Dmitrievich Dutov and Ol'ga Victorovna Serushkina and Maksim Aleksandrovich Korolev and Vadim Vadimovich Kachala and Yurii Andreevich Strelenko and Svyatoslav Arkad'evich Shevelev},
title = {Synthesis of quinolonecarboxylic acids from 1,3,5-trinitrobenzene},
journal = {Mendeleev Communications},
year = {2006},
volume = {16},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2006v016n06ABEH002390},
number = {6},
pages = {318--319},
doi = {10.1070/MC2006v016n06ABEH002390}
}
MLA
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Vorob'ev, Sergei Sergeyevich, et al. “Synthesis of quinolonecarboxylic acids from 1,3,5-trinitrobenzene.” Mendeleev Communications, vol. 16, no. 6, Dec. 2006, pp. 318-319. https://mendcomm.colab.ws/publications/10.1070/MC2006v016n06ABEH002390.

Abstract

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.

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