Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water

Shen, Wei; Wang, Limin; Tian, He; Tang, Jun; Yu, Jianjun

doi:10.1016/j.jfluchem.2009.02.014

Cited by 85 publications

(32 citation statements)

References 37 publications

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“…Also by comparison of their physical and spectroscopic data with those of authentic samples [27][28][29][30][31][32] .…”

Section: Resultsmentioning

confidence: 99%

SiO2/ZnCl2-Catalyzed Heterocyclic Synthesis: Green, Rapid and Efficient One-Pot Synthesis of 14-H-dibenzo [a, j]Xanthenes, 1,8-Dioxo-octahydroxanthenes and 1,8-Dioxo-Decahydroacridines Under Solvent-Free Conditions

2014

Chem Sci Trans

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A green and highly efficient protocol for the one-pot synthesis of a variety of 14-aryl-14-H-dibenzo [a,j]xanthenes and 9-aryl-1,8-dioxo-octahydroxanthenes has been developed via cyclocondensation of aryl aldehydes with 2-naphthol or dimedone using SiO 2 -ZnCl 2 (silzic) as a reusable heterogeneous catalyst under solvent-free reaction conditions. In addition, a one-pot, threecomponent condensation of aryl aldehydes, dimedone and ammonium acetate or aryl amines has been developed to furnish 9-aryl-1,8-dioxo-decahydroacridines in good to excellent yields under the same reaction conditions.

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“…Also by comparison of their physical and spectroscopic data with those of authentic samples [27][28][29][30][31][32] .…”

Section: Resultsmentioning

confidence: 99%

SiO2/ZnCl2-Catalyzed Heterocyclic Synthesis: Green, Rapid and Efficient One-Pot Synthesis of 14-H-dibenzo [a, j]Xanthenes, 1,8-Dioxo-octahydroxanthenes and 1,8-Dioxo-Decahydroacridines Under Solvent-Free Conditions

2014

Chem Sci Trans

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“…The desired products of high purity were obtained by column chromatography or recrystallization. [23] a Isolated yield of the pure product recrystallized from 75% aqueous ethanol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of N-substituted Acridinediones and Polyhydroquinoline Derivatives in Refluxing Water

Xia

Zhang

2012

Molecules

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Acridinediones were synthesized by the one-pot Hantzsch condensation of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, and aniline/4-methylaniline in refluxing water. This method has then been extended to the four-component reaction of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, ethyl acetoacetate and ammonium acetate for the synthesis of polyhydroquinoline derivatives. This is an environmentally friendly and efficient procedure providing good to excellent yields.

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“…However, when the mixture of aromatic amines substituted with electron-withdrawing group, dimedone and aromatic aldehydes was heated under optimized reaction conditions, 1,8-dioxooctahydroxanthenes 36 were formed (Table 3, entries 17 and 18). Based on Wang's report, 15 aromatic amines substituted with electron-withdrawing group did not have enough nucleophilicity to produce 1,8-dioxodecahydroacridines.…”

Section: Resultsmentioning

confidence: 99%

Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for the Synthesis of 1,8-Dioxodecahydroacridines Under Solvent-Free Conditions

Davoodnia¹,

Khojastehnezhad²,

Tavakoli‐Hoseini³

2011

Bulletin of the Korean Chemical Society

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Carbon-based solid acid catalyst was found to be highly efficient, eco-friendly and recyclable heterogeneous catalyst for the multicomponent reaction of dimedone, aromatic aldehydes, and a nitrogen source (ammonium acetate or aromatic amines) under solvent-free conditions, giving rise to 1,8-dioxodecahydroacridines in high yields. The present methodology offers several advantages, such as a simple procedure with an easy work-up, short reaction times, high yields, and the absence of any volatile and hazardous organic solvents.

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Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water

Cited by 85 publications

References 37 publications

SiO2/ZnCl2-Catalyzed Heterocyclic Synthesis: Green, Rapid and Efficient One-Pot Synthesis of 14-H-dibenzo [a, j]Xanthenes, 1,8-Dioxo-octahydroxanthenes and 1,8-Dioxo-Decahydroacridines Under Solvent-Free Conditions

SiO2/ZnCl2-Catalyzed Heterocyclic Synthesis: Green, Rapid and Efficient One-Pot Synthesis of 14-H-dibenzo [a, j]Xanthenes, 1,8-Dioxo-octahydroxanthenes and 1,8-Dioxo-Decahydroacridines Under Solvent-Free Conditions

Synthesis of N-substituted Acridinediones and Polyhydroquinoline Derivatives in Refluxing Water

Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for the Synthesis of 1,8-Dioxodecahydroacridines Under Solvent-Free Conditions

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