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Fokin, A. S.; Burgart, Yanina V.; Ryzhkov, O. V.; Салоутин, В. И.

doi:10.1023/a:1011325215083

Cited by 5 publications

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“…64 F + Attempts to bring the quinolone 62 into reaction with phenylhydrazine in ether were unsuccessful, while in alcohol they gave a mixture of unidentified substances [86].…”

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confidence: 99%

“…reaction of 4-quinolones 62 with aromatic binucleophiles (o-phenylenediamine, o-aminophenol) the corresponding quinolonylquinoxalones and quinolonylbenzoxazinones 63 are formed[86]. The reaction is conducted in alcohols (MeOH, BuOH) with the reagents in a ratio of 1Aminothiophenol reacts with compound 62 rather differently; it reacts with the carbonyl group in the ethoxycarbonyl group and substitutes the fluorine atom at position 7 of the aromatic ring.…”

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confidence: 99%

“…The reaction is conducted in alcohols (MeOH, BuOH) with the reagents in a ratio of 1Aminothiophenol reacts with compound 62 rather differently; it reacts with the carbonyl group in the ethoxycarbonyl group and substitutes the fluorine atom at position 7 of the aromatic ring. As considered by the authors, nucleophilic substitution in the fluoro aromatic ring is due to the high nucleophilicity of the sulfur atom of the aminothiophenol[86…”

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The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

107

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Data on methods for the construction of the 4-quinolone skeleton and modification of the substituents around it are reviewed. The "structure-activity" relationships of 4-quinolones are examined with respect to antibacterial and antitumor activity.Keywords: 4-quinolones, biological activity. 4-Quinolones have been a subject of research for many scientific teams, and this is reflected in the numerous reviews and monographs devoted to various aspects of the subject. One of the early reviews [1] concerns aspects of the synthesis of individual representatives of the group of 4-quinolones and comparative characterization of their antimicrobial activity. Basic approaches to construction of the fluoroquinolone skeleton and also variation of the substituents at various positions of the ring were examined in the review [2]. The relationship between the structure and antibacterial activity is discussed in [3], and methods for the synthesis of polycyclic derivatives of 4-quinolones based on the annelation of rings to the various faces of the quinoline skeleton are discussed in the review [4]. The reviews [5, 6] were devoted to identification of the structural modifications of 4-quinolones responsible for their conversion from antibacterial agents to antitumor agents. The molecular and biological aspects of the antibacterial action of 4-quinolone-3-carboxylic acids are examined in [7], and issues concerned with the clinical application of 4-quinolones are discussed in the reviews [8][9][10][11][12] and in the monograph [13]. The synthesis and the "structure-activity" relationships of the bioisosteres of 4-quinolones -2-pyridones -are examined in the review [14].The aim of the present review was to classify existing methods for the synthesis not only of fluoroquinolones but also of any 4-quinolones, to demonstrate the effects of modification of the molecule at all positions, to summarize data on the various types of activity, and to examine the "structure-activity" relationship with respect to antibacterial and antitumor activity.

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“…64 F + Attempts to bring the quinolone 62 into reaction with phenylhydrazine in ether were unsuccessful, while in alcohol they gave a mixture of unidentified substances [86].…”

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confidence: 99%

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The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

107

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“…We previously synthesized ethyl 2-(1-aryl-5,6,7,8tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetates and their numerous derivatives [3][4][5]. The goal of the present work was to obtain fluorine-containing 2-(1-aryl-4-oxo-1,4-dihydrocinnolin-3-yl)-2oxoacetic acids.…”

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confidence: 99%

Synthesis of Fluorine-Containing 2-(1-Aryl-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic Acids

et al. 2005

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Acid hydrolysis of ethyl 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetates gives 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2,2-dihydroxyacetic acids which undergo dehydration on heating in toluene to afford 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3yl)-2-oxoacetic acids. Reactions of the latter with excess morpholine result in replacement of two fluorine atoms in positions 5 and 7 by the amine residues.

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ChemInform Abstract: Reactions of 1‐Aryl(alkyl)‐3‐ethoxalyl‐5,6,7,8‐tetrafluoro‐1,4‐dihydrocinnolin (quinolin)‐4‐ones with Aromatic Dinucleophiles.

et al. 2001

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Reactionsof 1-Aryl(alkyl)-3-ethoxalyl-5,6,7,8-tetrafluoro-1,4dihydrocinnolin (quinolin)-4-ones with Aromatic Dinucleophiles. -The reaction of title compounds (I) with o-aminophenol and o-phenylenediamine proceeds at the dicarbonyl side chain furnishing hetaryl-substituted quinoxalones and benzoxazinones [cf. (III)], respectively. However, o-aminobenzenethiol acts as both an S-nucleophile replacing one F-atom and an N-nucleophile replacing the keto group in the side dicarbonyl fragment [→(V)]. Under more drastic reaction conditions, cyclization of substitution product (Va) can be achieved yielding benzothiazinones (VI). -(FOKIN, A. S.; BURGART, YA. V.; RYZHKOV, O. V.; SALOUTIN, V. I.; Russ.

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Cited by 5 publications

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The methods of synthesis, modification, and biological activity of 4-quinolones (review)

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Synthesis of Fluorine-Containing 2-(1-Aryl-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic Acids

ChemInform Abstract: Reactions of 1‐Aryl(alkyl)‐3‐ethoxalyl‐5,6,7,8‐tetrafluoro‐1,4‐dihydrocinnolin (quinolin)‐4‐ones with Aromatic Dinucleophiles.

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