Synthesis of 2-trifluoromethyl-1(substituted aryl)-4(1H)-quinolones using trifluoroacetamidoyl chlorides

López, Simón E.; Rebollo, Oscar; Salazar, José A.; Charris, Jaime; Yanez, Ciceron O.

doi:10.1016/s0022-1139(02)00288-9

Cited by 14 publications

(10 citation statements)

References 14 publications

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“…During the reaction of substituted anilines with ethyl aroylacetate in the presence of polyphosphoric acids the substituted 2-aryl-4-quinolones 23 and 24 are formed [53]. The derivative 26, produced by successive transformations from benzoic acids (or acid halides) [55][56][57] or α-(nitro)acetophenones [58,59] and DMF acetal [59] or ethyl 3-(dialkylamino)acrylate [55,60], was hydrolyzed and decarboxylated, and the product was then condensed with ethyl orthoformate or DMF acetal in acetic anhydride. The obtained compound 27 was transaminated by the action of primary amines, making it possible to introduce various substituents at position 1.…”

Section: Type Dmentioning

confidence: 99%

“…The cyclization of compounds 28 leading to the formation of 4-quinolones 29 can be realized in the presence of various reagents: sodium ethoxide in ethanol [61]; KF in DMF [60]; K 2 CO 3 or Li 2 CO 3 in DMF [26,55,56,58,60,[62][63][64] or acetonitrile or NaH in dioxane [57] or THF [62]; triethylamine in DMF [65], DMSO [59], or toluene [57,59,60].…”

Section: Type Dmentioning

confidence: 99%

“…Tricyclic compounds containing a 4-quinolone fragment [61], analogs of ofloxacin [63], and pentacyclic derivatives [66] can also be obtained by this method. At position 3 of the 4-quinolones there is usually a carboxyl or alkoxycarbonyl group [55,56,60,[63][64][65][66][67], although there may be a nitro group [59], a CN group [68], or H [58,69]. Moreover, the scheme can also used to obtain the quite rare 2-substituted 4-quinolones (carboxyl group [69], trifluoromethyl group [58]).…”

Section: Type Dmentioning

confidence: 99%

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

Boteva

Красных

2009

Chem Heterocycl Comp

109

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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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Section: Type Dmentioning

confidence: 99%

Section: Type Dmentioning

confidence: 99%

Section: Type Dmentioning

confidence: 99%

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

Boteva

Красных

2009

Chem Heterocycl Comp

109

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“…However, this transformation requires a good alkylating agent and cannot be used for the synthesis of N-arylated 2-R F -4-quinolones. Very recently there has been a communication [8] of the reaction of N-arylated trifluoroacetimidoyl chlorides with 2-chloroacetophenones followed by the cyclization of the intermediate aminoenones to give 1-aryl-2-trifluoromethyl-4-(1H)-quinolones. We have found that the condensation of 2-anilinoacetophenone with R F CO 2 Et on boiling in THF for 1 h in the presence of LiH using a 1:1.2 molar ratio of ketone to ester affords previously unknown Nphenyl-2-R F -4-quinolones 1a-c in 90-93% yields.…”

Section: Resultsmentioning

confidence: 99%

“…The growing importance of the fluoroquinolone antibiotics has led to increased interest in the synthesis of 2-polyfluoroalkyl-4-quinolones [1][2][3][4][5][6][7][8][9][10]. It is known that 2-(trifluoroacetylamino)acetophenones undergo cyclization in the presence of alkylating agents and KOH to form Nalkyl-2-trifluoromethyl-4-quinolones [9].…”

Section: Introductionmentioning

confidence: 99%

A simple and highly efficient synthesis of N-phenyl-2-polyfluoroalkyl-4-quinolones from 2-anilinoacetophenone and RFCO2Et

Usachev¹,

Sosnovskikh²

2004

Journal of Fluorine Chemistry

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Copper(I)‐Catalyzed Coupling Cyclization of Methyl Perfluoroalk‐2‐ynoates with 2‐Aminobenzonitriles: Synthesis of 2‐Perfluoroalkylated Quinolines

et al. 2013

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Synthesis of 2-trifluoromethyl-1(substituted aryl)-4(1H)-quinolones using trifluoroacetamidoyl chlorides

Cited by 14 publications

References 14 publications

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

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

A simple and highly efficient synthesis of N-phenyl-2-polyfluoroalkyl-4-quinolones from 2-anilinoacetophenone and RFCO2Et

Copper(I)‐Catalyzed Coupling Cyclization of Methyl Perfluoroalk‐2‐ynoates with 2‐Aminobenzonitriles: Synthesis of 2‐Perfluoroalkylated Quinolines

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