A Mild and Efficient Synthesis of 4-Quinolones and Quinolone Heterocycles

Zewge, Daniel; Chen, Cheng‐yi; Deer, Curtis; Dormer, Peter G.; Hughes, D. L.

doi:10.1021/jo070181o

Cited by 115 publications

(61 citation statements)

References 20 publications

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“…sulfuric acid in mixture with acetic anhydride [1], and Eaton's reagent (a mixture of phosphorus(V) oxide and methanesulfonic acid) [37,40]. With the latter it is possible to reduce the cyclization temperature from 140°C (if polyphosphoric acid is used as cyclization agent) to 50°C (!)…”

Section: Type Dmentioning

confidence: 99%

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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Section: Type Dmentioning

confidence: 99%

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

Boteva

Красных

2009

Chem Heterocycl Comp

107

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“…Although the latter reaction (e) is well-known as described above (Eq. 10) and in reference [64][65][66][67][68][69], step (d) does not occur as shown in the gold-catalyzed reaction of EDA in the absence of amine; this reaction gives the carbene coupled products (Eq. 2) [25].…”

Section: Mechanistic Considerations For the Gold-catalyzedmentioning

confidence: 88%

Bulk Gold-Catalyzed Reactions of Diazoalkanes with Amines and O2 to Give Enamines

2010

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Bulk gold powder, consisting of approximately 5-50 lm particles, catalyzes reactions of diazoalkanes E(H)C=N 2 , where E is CO 2 Et or PhC(O), with amines R 1 R 2 NH and O 2 to give enamine products (R 1 R 2 N) (E)C=CH(E) in 58-94% yield. The reactions are proposed to occur by initial formation of surface-bound (E)(H)C: carbene groups that are attacked by nucleophilic amines. The enamine products are very different than those obtained in reactions catalyzed by homogeneous transition metal complexes. These reactions of diazoalkanes, amines, and O 2 represent a new type of bulk gold-catalyzed reaction.

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“…8 The first step was the formation of enamine I by the reaction between p-phenylenediamine and dimethyl acetylenedicarboxylate (DMAD) in alcoholic solvents. Finally, the enamine was cyclized to the corresponding bis-quinolones II using Eaton's reagent as an efficient cyclizing agent.…”

Section: (B) Synthesis Of Bis-n-heterocyclic Carbene (Nhc) Precursorsmentioning

confidence: 99%

Well-Documented Applications of p-Phenylenediamine in the Synthesis of Heterocycles and Heterocrown Ethers

Koner¹

2010

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research Well-Documented Applications of p-Phenylenediamine in the Synthesis of Heterocycles and Heterocrown EthersCompiled by Rik Rani Koner Rik Rani Koner was born in Bankura, West Bengal, India in 1980. She received her M.Sc. degree ( 2004) in organic chemistry from Visva-Bharati University. In the meantime, she received her Ph.D. degree under the supervision of Professor Manabendra Ray. Her research interests focus on the synthesis and characterization of metallo-organic frameworks and aniline-based polymers with functional groups.

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A Mild and Efficient Synthesis of 4-Quinolones and Quinolone Heterocycles

Cited by 115 publications

References 20 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)

Bulk Gold-Catalyzed Reactions of Diazoalkanes with Amines and O2 to Give Enamines

Well-Documented Applications of p-Phenylenediamine in the Synthesis of Heterocycles and Heterocrown Ethers

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