Cyclization of amine‐acetylene diester adducts: A modification of the conrad‐limpach method

Heindel, Ned D.; Brodof, Terry A.; Kogelschatz, Jane E.

doi:10.1002/jhet.5570030224

Cited by 42 publications

(16 citation statements)

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“…Chemists are considerably eager to the synthesis of quinolines due to the contribution of their oxygen heterocycles to potential antimalarial, antibacterial, antiasthmatic, antihypertensive, anti‐inflammatory, antiplatelet and tyro kinase PDGF‐RTK inhibiting properties . Although different methods including the Skraup, Conrad–Limpach–Knorr,, Pfitzinger,, Friedländer,, and Combes, have been reported for the synthesis of quinolines but the Friedländer condensation is the method which is still a popular method for the synthesis of quinolone derivatives, which in, 2‐amino benzophenone condenses with ketones or diketones to yield quinolines . Nevertheless, for the efficient preparation of heterocycles containing quinolone fragment, the development of new synthetic methods is, therefore, an interesting challenge.…”

Section: Introductionmentioning

confidence: 99%

CoFe₂O₄@SiO₂@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water

2019

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In this study, a description is made upon the preparation, characterization and catalytic application of CoFe 2 O 4 @SiO 2 @Co (III) salen complex, i. e., Co(III) salen complex loaded on cobalt ferrite-silica nanoparticle. TEM, SEM-EDX, VSM, FT-IR analyses were used to characterize the complex. Thermal gravimetric analysis (TGA) was also used to determine the thermal stability of the material. Using Scherrer's approximation, an average crystallite size is determined from the full width at half maximum of strongest reflection by powder X-ray diffractometry (XRD). The efficiency is studied for CoFe 2 O 4 @SiO 2 @Co(III) salen complex in quinolines of various 1,3-dicarbonyls synthesizing with 2-aminobenzophenone. Good to excellent yields (85-96%) are given to corresponding products by excellent catalytic activity that is demonstrated by the nanocatalyst. Moreover, the investigation of CoFe 2 O 4 @SiO 2 @Co(III) salen complex revealed that nanocatalyst could be recovered and reused at least five times without any appreciable decrease in activity and selectivity. This confirms its high efficiency and high stability under the reaction conditions and during recycling stages.

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Section: Introductionmentioning

confidence: 99%

CoFe₂O₄@SiO₂@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water

2019

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“…Studies have shown that, substituted 2‐cyanoquinoline derivatives possess higher in vitro and in vivo 5‐LOX inhibiting property while comparing with commercial drugs ,. 2‐Substituted 4‐phenylquinolines can act as a Potential Antidepressant Drug .…”

Section: Introductionmentioning

confidence: 99%

Porphyrin Cored Amine Functionalized Dendritic Polymer: An Efficient Reusable Catalyst for Quinoline Synthesis

et al. 2019

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A novel porphyrin cored amine functionalized dendritic polymer was effectively synthesized by divergent method. It was identified as an effective homogeneous organo catalyst for the synthesis of quinoline derivatives, from aromatic aldehyde, aromatic amine and malononitrile. The reaction was completed within one hour with high yield (87% ‐ 93%) in 2:1 ratio of water and ethanol medium at 60 °C. Porphyrin cored dendritic polymer has a number of amino groups on its surface; hence it acts as a very good base catalyst. Separation and reuse of the catalyst from the product was easy due to its water soluble nature. This is the first reported synthesis of Quinoline derivatives using dendritic polymer as an organo catalyst.

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“…7,8 The synthesis of quinolines has been of considerable interest to chemists because their oxygen heterocycles may contribute to potential antimalarial, antibacterial, antiasthmatic, antihypertensive, antiinflammatory, antiplatelet and tyro kinase PDGF-RTK inhibiting properties. [9][10][11][12][13][14][15][16] For the synthesis of quinolines, various methods have been reported including the Skraup, 17 Conrad-Limpach-Knorr, 18,19 Pfitzinger, 20,21 Friedländer, 22,23 and Combes. 24,25 However, the Friedlander condensation is still considered as a popular method for the synthesis of quinoline derivatives.…”

Section: Introductionmentioning

confidence: 99%

PEG-SO3H as a catalyst in aqueous media: A simple, proficient and green approach for the synthesis of quinoline derivatives

2013

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A convenient and efficient method was developed for the synthesis of quinolines, an important class of potentially bioactive compounds. The quinoline derivatives were prepared in water, an excellent solvent in terms of environmental impact and with reduced waste production. PEG-SO 3 H effectively catalysed the one-pot synthesis of quinolines by the condensation of o-aminoaryl ketones and carbonyl compound with high yields (75-95%). The compounds were isolated by simple filtration in a high purity form.

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Cyclization of amine‐acetylene diester adducts: A modification of the conrad‐limpach method

Cited by 42 publications

References 5 publications

CoFe₂O₄@SiO₂@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water

CoFe₂O₄@SiO₂@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water

Porphyrin Cored Amine Functionalized Dendritic Polymer: An Efficient Reusable Catalyst for Quinoline Synthesis

PEG-SO3H as a catalyst in aqueous media: A simple, proficient and green approach for the synthesis of quinoline derivatives

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Cyclization of amine‐acetylene diester adducts: A modification of the conrad‐limpach method

Cited by 42 publications

References 5 publications

CoFe2O4@SiO2@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water

CoFe2O4@SiO2@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water

Porphyrin Cored Amine Functionalized Dendritic Polymer: An Efficient Reusable Catalyst for Quinoline Synthesis

PEG-SO3H as a catalyst in aqueous media: A simple, proficient and green approach for the synthesis of quinoline derivatives

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Product

Resources

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CoFe₂O₄@SiO₂@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water

CoFe₂O₄@SiO₂@Co(III) Salen Complex: A Magnetically Recyclable Heterogeneous Catalyst for the Synthesis of Quinoline Derivatives in Water