Synthesis of 4-quinolones, benzopyran derivatives and other fused systems based on the domino ANRORC reactions of (ortho-fluoro)-3-benzoylchromones

Iaroshenko, Viktor O.; Mkrtchyan, Satenik; Gevorgyan, Ashot; Grigoryan, Tatevik; Villinger, Alexander; Langer, Peter

doi:10.1039/c5ra02978c

Cited by 24 publications

(22 citation statements)

References 81 publications

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“…Another transition‐metal‐free strategy for the synthesis of 4‐quinolones through a domino reaction of 3‐benzoyl‐chromones 46 with aliphatic amines is outlined in Scheme . All reactions responded well and provided the desired products ranging from moderate to excellent yields, with high chemoselectivity.…”

Section: Development In the Syntheses Of 4‐quinolonesmentioning

confidence: 99%

Synthesis and Functionalization of 4‐Quinolones – A Progressing Story

Ghosh

Das

2019

Eur J Org Chem

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4‐Quinolone derivatives are serving as active components in diverse families of drugs such as antibacterial, antiviral, antimalarial, anticancer, antitumor and anti‐HIV agents. They have also attracted the significant attention in synthetic chemistry due to their prolific development, pharmacokinetic properties and good tolerability. Recent years have observed an upsurge in the modification of the 4‐quinolone scaffold. This review covers (2002 to 2019) the progress of the developments in the syntheses as well as functionalization of 4‐quinolones in different positions.

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Section: Development In the Syntheses Of 4‐quinolonesmentioning

confidence: 99%

Synthesis and Functionalization of 4‐Quinolones – A Progressing Story

Ghosh

Das

2019

Eur J Org Chem

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“…Anal. Calcd for C 17 To a hot solution of carboxaldehyde 1 (0.61 g, 3 mmol) in 95% ethanol (20 mL), o-phenylenediamine (0.33 g, 3 mmol) was added and stirred for 1 min. The resulting orange crystals were filtered off and crystallized from EtOH to give compound 10 as orange crystals, mp 205°C, yield 0.78 g (79% A mixture of carboxaldehyde 1 (0.61 g, 3 mmol) and o-phenylenediamine (0.33 g, 3 mmol) in 95% ethanol (20 mL) was heated under reflux for 2 h. After cooling, the resulting yellow solid was filtered off and crystallized from DMF/EtOH to give compound 11 as white crystals, mp 283-284°C, yield 0.63 g (77%).…”

Section: 8-dimethylchromone-3-carboxylic Acid (3)mentioning

confidence: 99%

“…C‐2 is more electrophilic than the other carbon atoms. The chemistry of 3‐substituted chromones is more varied, and their chemical behavior depends widely on the type of the functional group present at C‐3 position . Chromones bearing electron‐withdrawing substituents in the 3‐position react with 1,2‐dinucleophiles and 1,3‐dinucleophiles delivering the corresponding five‐membered and six‐membered heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Studies on the Chemical Reactions of Some 3‐Substituted‐6,8‐dimethylchromones with Nucleophilic Reagents

Ibrahim

Badran

El‐Gohary

et al. 2018

Journal of Heterocyclic Chem

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A variety of 3‐substituted‐6,8‐dimethylchromones have been synthesized and characterized. The chemical reactivity of 3‐substituted‐6,8‐dimethylchromones was studied towards some nucleophiles, namely, S‐benzyldithiocarbazate, o‐phenylenediamine, and cyanoacetamide, and a diversity of products were efficiently synthesized. Reactions of 3‐substituted‐6,8‐dimethylchromones (except 3‐formyl‐6,8‐dimethylchromone), with nucleophilic reagents, usually proceed through nucleophilic attack at C‐2 position followed by different types of heterocyclization depending on the functional group present at C‐3 position. Structures of the newly synthesized products have been established based on elemental analysis and spectral data.

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“…Recently, enaminone derivatives represent a good source for synthesis of a diversity of 3‐substituted chromones 14–16 . The chemical behavior of chromones is extensively different depending on the substituent present at position 3 17–19 . 3‐Substituted chromones reacted with binucleophilic reagents giving a diversity of heterocyclic systems 20–22 .…”

Section: Introductionmentioning

confidence: 99%

Reactivity of some 3‐substituted‐6,8‐dimethylchromones toward some nucleophilic reagents

Badran

El‐Gohary

Ibrahim

et al. 2020

Journal of Heterocyclic Chem

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The reactivity of 3‐substituted‐6,8‐dimethylchromone derivatives 1‐5 was investigated toward selected nucleophilic reagents namely; 3‐amino‐1,2,4‐triazole, 2‐aminobenzimidazole, 7‐chloro‐4‐hydrazinoquinoline, and 5,6‐diphenyl‐3‐hydrazino‐1,2,4‐triazine. These nucleophiles were allowed to react with 6,8‐dimethylchromone‐3‐carboxaldehyde (1) through condensation with the aldehyde group with opening of γ‐pyrone ring giving compounds 6, 7, 10, and 11. Reactions with 6,8‐dimethylchromone‐3‐carbonitrile (2), and 6,8‐dimethylchromone‐3‐carboxylic acid (3) occur via attack at position 2 in both compounds followed by cycloaddition onto the nitrile function (in case of carbonitrile 2) or decarboxylation and cyclocondensation with the carbonyl group (in case of carboxylic acid 3). The current nucleophilic reagents reacted with simple condensation products 4 and 5, in boiling dioxane, through nucleophilic addition at the exocyclic vinyl bond followed by addition at the CN group giving 6,8‐dimethylchromone linked various heterocyclic systems 20‐27.

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Synthesis of 4-quinolones, benzopyran derivatives and other fused systems based on the domino ANRORC reactions of (ortho-fluoro)-3-benzoylchromones

Abstract: This method provides a valuable one-pot shortcut for the synthesis of 4-quinolones, benzopyran derivatives and other fused systems from (ortho-fluoro)-3-benzoylchromones.

Cited by 24 publications

References 81 publications

Synthesis and Functionalization of 4‐Quinolones – A Progressing Story

Synthesis and Functionalization of 4‐Quinolones – A Progressing Story

Studies on the Chemical Reactions of Some 3‐Substituted‐6,8‐dimethylchromones with Nucleophilic Reagents

Reactivity of some 3‐substituted‐6,8‐dimethylchromones toward some nucleophilic reagents

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