Thermochemical reaction of 7-azido-1-ethyl-6,8-difluoroquinolone-3-carboxylate with heterocyclic amines. An expeditious synthesis of novel fluoroquinolone derivatives

Leyva, Socorro; Leyva, Elisa

doi:10.1016/j.tet.2006.11.079

Cited by 21 publications

(7 citation statements)

References 20 publications

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“…In recent years, there has been increasing interest in the synthesis of alkyl azide, this stems from its applicability for synthesis of polyfunctionally substituted heterocycles [14][15][16]. Thus, thiazolopyrimidinylacetyl azide 12 was synthesized following the reported method [17] by stirring equimolar amounts of [7-(dibenzothien-2-yl)-5-phenyl-2,3-dihydro-5H-thiazolo[3,2-b]pyrimidin-6-yl]acetyl chloride and aqueous sodium azide in dry acetone at 0-5 °C, (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

A facile synthesis and heteroannulation of thiazolopyrimidine and related heterocyclic systems

Aly¹

2008

Journal of Heterocyclic Chem

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Reaction of pyrimidinylacetic acid 2 with different electrophilic and nucleophilic reagents gave annulated pyrimidine derivatives 3‐11, respectively. Compound 3 was transformed to pyrimidinylacetyl azide 12, which upon heterocyclization with active methylene compounds, acidic and basic reagents furnished functionally substituted heteroaromatic compounds 13‐21, respectively. The antimicrobial activity of some synthesized compounds was investigated. The structures of the synthesized derivatives were elucidated by elemental and spectral analyses.

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Section: Resultsmentioning

confidence: 99%

A facile synthesis and heteroannulation of thiazolopyrimidine and related heterocyclic systems

Aly¹

2008

Journal of Heterocyclic Chem

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“…If the amine cannot be brought directly into reaction with the 7-fluoro-substituted 4-quinolone, e.g., on account of low nucleophilicity, the approach [98,99] based on the synthesis of the azide 106 and its subsequent reaction with the heterocyclic amines can be used.…”

Section: Insertion Of a Substituent At Position 7 With The Formation mentioning

confidence: 99%

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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“…10 1,3-Diethoxycarbonyl-4-quinolones 1g – k were prepared by usual N-ethoxycarbonylation 14 of the corresponding 3-ethoxycarbonyl-4-quinolones. 16 Polyhalogenated 4-quinolones 1m (17) is commercially available and 1n (18) was prepared from its commercially available carboxylic acid by usual esterification with MeI-K 2 CO 3 /DMF at 50 °C for 12 h.…”

Section: Methodsmentioning

confidence: 99%

Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones

et al. 2019

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The electroreductive coupling of 1-alkoxycarbonyl-4-quinolones with benzophenones in the presence of trimethylsilyl chloride gave adducts reacted at the 2-position of 4-quinolones as trimethylsilyl ethers. The adducts were transformed to 2-(diarylhydroxymethyl)-4-quinolones. The electroreduction of 1,3-diethoxycarbonyl-4-quinolones and polyhalogenated 3-alkoxycarbonyl-1-alkyl-4-quinolones with benzophenones also gave adducts reacted at the 2-position of 4-quinolones. On the contrary, the electroreductive coupling of 1,3-diethooxycarbonyl-8-methoxy-4-quinolones occurred at the 4-position of 4-quinolones to give 4-substituted quinolines.

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Thermochemical reaction of 7-azido-1-ethyl-6,8-difluoroquinolone-3-carboxylate with heterocyclic amines. An expeditious synthesis of novel fluoroquinolone derivatives

Cited by 21 publications

References 20 publications

A facile synthesis and heteroannulation of thiazolopyrimidine and related heterocyclic systems

A facile synthesis and heteroannulation of thiazolopyrimidine and related heterocyclic systems

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

Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones

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