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Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids

Oleg Nikolaevich Chupakhin 1
Oleg Nikolaevich Chupakhin
, 
Yurii Alexeevich Azev 2
Yurii Alexeevich Azev
, 
Sergei Gennad'evich Alexeev 3
Sergei Gennad'evich Alexeev
, 
Sergei Victorovich Shorshnev 2
Sergei Victorovich Shorshnev
, 
Elizaveta Vladimirovna Tsoi 4
Elizaveta Vladimirovna Tsoi
, 
10.1070/MC1992v002n04ABEH000180
Published 1992-12-31
Communication , Volume 2, Issue 4, 151-153
9
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Chupakhin O. N. et al. Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids // Mendeleev Communications. 1992. Vol. 2. No. 4. pp. 151-153.
GOST all authors (up to 50) Copy
Chupakhin O. N., Azev Y. A., Alexeev S. G., Shorshnev S. V., Tsoi E. V., Charushin V. N. Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids // Mendeleev Communications. 1992. Vol. 2. No. 4. pp. 151-153.
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TY - JOUR
DO - 10.1070/MC1992v002n04ABEH000180
UR - https://mendcomm.colab.ws/publications/10.1070/MC1992v002n04ABEH000180
TI - Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids
T2 - Mendeleev Communications
AU - Chupakhin, Oleg Nikolaevich
AU - Azev, Yurii Alexeevich
AU - Alexeev, Sergei Gennad'evich
AU - Shorshnev, Sergei Victorovich
AU - Tsoi, Elizaveta Vladimirovna
AU - Charushin, Valery Nikolaevich
PY - 1992
DA - 1992/12/31
PB - Mendeleev Communications
SP - 151-153
IS - 4
VL - 2
ER -
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@article{1992_Chupakhin,
author = {Oleg Nikolaevich Chupakhin and Yurii Alexeevich Azev and Sergei Gennad'evich Alexeev and Sergei Victorovich Shorshnev and Elizaveta Vladimirovna Tsoi and Valery Nikolaevich Charushin},
title = {Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids},
journal = {Mendeleev Communications},
year = {1992},
volume = {2},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1992v002n04ABEH000180},
number = {4},
pages = {151--153},
doi = {10.1070/MC1992v002n04ABEH000180}
}
MLA
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Chupakhin, Oleg Nikolaevich, et al. “Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids.” Mendeleev Communications, vol. 2, no. 4, Dec. 1992, pp. 151-153. https://mendcomm.colab.ws/publications/10.1070/MC1992v002n04ABEH000180.

Abstract

Reactions of 7-(X)-substituted ethyl 1-amino-4-oxo-1,4-dihydroquinoline-3-carboxylates (1a-c; X = F, Cl and 4-methylpiperazin-1-yl) with mono- and di-ketones have been studied. Treatment of 1a; X = F with cyclopentanone and cyclopentanone in acetic acid resulted in the corresponding azomethynes; α-dicarbonyl compounds such as glyoxal, glyoxylic acid or ethyl pyruvate caused desamination of 1a into ethyl, 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, while reactions of 1a-c with acetoacetone resulted in tricyclic 7-fluoro-4-oxopyrazolo[1,5-a]quinoline-4-carboxylic acids

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