Synthesis of Some New Fluorinated Hexahydroquinoline and Acridinedione Derivatives in Trifluoroethanol

Okoro, Cosmas O.; Ogunwale, Mumiye A.; Siddiquee, Tasneem A.

doi:10.3390/app2020368

Cited by 10 publications

(7 citation statements)

References 14 publications

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“…For biological activities of hydroquinolines, see: Moghadam et al (2011); Miri et al (2007). For accridinones, see: Okoro et al (2012). For dihydropyridines, see: Aydin et al (2006); Rose (1990Rose ( , 1991; Rose & Draeger (1992)…”

Section: Related Literaturementioning

confidence: 99%

“…Hydroquinolines (Moghadam et al, 2011;Miri et al, 2007), acridinediones (Okoro et al, 2012) and other anellated dihydropyridines (Aydin et al, 2006;Rose, 1990) were developed that exhibit selective cardial agonist activity while calcium antagonistic effects were observed on smooth musculature (Rose & Draeger, 1992;Rose, 1991). In this context, we report here the synthesis and crystal structure of the title compound, C 23 H 24 BrNO 5 , (I).…”

Section: S1 Commentmentioning

confidence: 99%

See 1 more Smart Citation

Crystal structure of ethyl 2-[9-(5-bromo-2-hydroxyphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-10-yl]acetate

et al. 2015

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In the title compound, C23H24BrNO5, the central 1,4-dihydropyridine ring of the 1,2,3,4,5,6,7,8,9,10-decahydroacridine ring system adopts a half-chair conformation. The two cyclohexene rings fused to the central ring both have a twisted-boat conformation. The mean planes of the bromohydroxyphenyl ring and the major and minor components of the disordered ethyl aminoacetate moiety make dihedral angles of 78.99 (12), 85.9 (2) and 88.3 (9)°, respectively, with the 1,4-dihydropyridine ring. The terminal ethyl group of the ethyl aminoacetate moiety is disordered over two sets of sites with refined occupancies of 0.768 (17) and 0.232 (17). The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, forming an S(8) ring motif. In the crystal, C—H⋯O hydrogen bonds connect the molecules into layers parallel to (001), enclosing R 1 2(7) ring motifs.

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

Crystal structure of ethyl 2-[9-(5-bromo-2-hydroxyphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-10-yl]acetate

et al. 2015

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“…Synthesis of Some New Fluorinated Hexahydroquinoline and Acridinedione Derivatives in Trifluoroethanol is the article contribution by Cosmas Okoro, Mumiye Ogunwale and Tasneem Siddiquee [14] in which they describe a facile one-pot synthesis of new fluorinated hexahydroquinoline derivatives via an unsymmetric Hantzsch reaction utilizing 5-trifluoromethyl-1,3-cyclohexanedione, aldehydes, acetoacetate ester, and ammonium acetate in trifluoroethanol. The reaction is simple and rapid with high yield.…”

Section: Synthesis/applications Of Organo-fluorine Moleculesmentioning

confidence: 99%

Special Feature Organo-Fluorine Chemical Science

Hügel

Jackson

2012

Applied Sciences

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Inventing the Fluorine FutureFluorine is the 13th most abundant element and, with other fluorine containing functional groups, is a most effective element in biological substances, pharmaceuticals, agrochemicals, liquid crystals, dyes, polymers and a wide range of consumer products. This reflects its resistance to metabolic change due to the strength of the C-F bond providing biological stability and the application of its nonstick-interfacial physical characteristics. Its introduction often remains a synthetic challenge. The widespread use of organofluorines has increased the demand for the development of practical and simple reagents and experimental strategies for the incorporation of fluorine into all types of molecular structures and this was the reasoning behind this special feature on Organo-Fluorine Chemical Science.The contributed articles belong to two broad groups: (i) preparation of fluorine materials, polymers; (ii) the synthesis/applications of organo-fluorine molecules. Fluorine-Fatness-Due to Lack of FitnessTheoretical [1] and experimental observations to explain the molecular origins of fluorocarbon hydrophobicity suggest that the hydrophobicity of a fluorocarbon, whether the interaction with water is as solute or as surface, is due to its "fatness". In solution, the extra work of cavity formation to accommodate a fluorocarbon, compared to a hydrocarbon, is not offset by enhanced energetic interactions with water. The enhanced hydrophobicity of fluorinated surfaces arises because fluorocarbons pack less densely on surfaces leading to poorer van der Waals interactions with water. The interaction of water with a hydrophobic solute/surface is primarily a function of van der Waals interactions and is substantially independent of electrostatic interactions. This independence is primarily due to the strong tendency of water at room temperature to maintain its hydrogen bonding network structure at an interface lacking hydrophilic sites. OPEN ACCESS

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“…[33] Generally, 1,4-dihydropyridine derivatives are synthesized commonly via Hantzsch reaction using cyclohexane-1,3-dione, aldehydes, β-ketoesters and different amines. [34][35][36][37] These Nheterocycles are prepared in the presence of various recyclable catalysts such as NiO/ZrO 2 , [38] nanocrystalline CdS thin film, [39] cellulose template embedded Cu bionanocomposite, [40] γcyclodextrin, [41] nicotinic acid, [42] amine-functionalized graphene oxide nanosheets, [43] [PVP-SO 3 H] HSO 4 , [44] NiFeTi calcined layered double hydroxides, [45] periodic mesoporous organosilica supported manganese, [46] highly monodisperse PdRuNi nanoparticles on graphene oxide, [47] and Fe 3 O 4 @SiO 2 nanoparticles. [48] These methods offer several advantages such as short reaction times, good yields, excluding toxic solvents, easy recovery and recyclability of the catalyst, without the significant loss of yield after many runs.…”

Section: Introductionmentioning

confidence: 99%

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

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Cyclohexane‐1,3‐dione and its derivatives are imperative precursors in synthetic organic chemistry as they are useful intermediates for the synthesis of a wide range of biologically active natural products, heterocycles and pharmaceuticals. Recently, cyclohexane‐1,3‐diones have been used for the synthesis of varied array of six‐membered nitrogen‐containing heterocycles in the presence of aldehydes, acetoacetic esters, malononitrile, chalcones, coumarins, acetophenones, amino acids, amines, etc. under catalytic and non‐catalytic conditions. Newest studies on the importance of these heterocycles motivated us to compile all the recently developed processes which include the fabrication of six‐membered nitrogen heterocycles. This article is mainly focused on the efficient synthesis of six‐membered N‐heterocycles i. e. 1,4‐dihydropyridine, acridine‐1,8‐diones, benzoacridinones, quinolones and pyridine derivatives from cyclohexane‐1,3‐diones as one of the substrates, published for the last ten years.

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Synthesis of Some New Fluorinated Hexahydroquinoline and Acridinedione Derivatives in Trifluoroethanol

Cited by 10 publications

References 14 publications

Crystal structure of ethyl 2-[9-(5-bromo-2-hydroxyphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-10-yl]acetate

Crystal structure of ethyl 2-[9-(5-bromo-2-hydroxyphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-10-yl]acetate

Special Feature Organo-Fluorine Chemical Science

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

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