Paper Titles
Effects of Nanoscale Zero-Valent Iron on Soil-Leaching of Trinitrotoluene Contaminated Soil in Acid Rain Conditions
p.66
A Novelty Analytical Approach to Determine Oxidation States in Complex Refractory Oxides Containing Iron, Uranium, Cerium and other Mixed Valence Cations
p.77
Study on the Growth Mechanism of Chlorocarbon Radicals on the Surface of CVD Diamond (100)
p.83
Inhibitory Potential of Artificial Saliva Containing Vanillin against Biofilm Formation of Candida
p.91
One-Pot Synthesis of 2-Phenylquinoline-4-Carboxylic Acid: Iron(III) Trifluoromethanesulfonate Catalysed Doebner Reaction
p.97
Research Progress in the Application of CuS Nanoparticles in Tumor Diagnosis and Treatment
p.103
Protecting the Hull of High-Speed Crafts against Slamming Loads Using Hybrid Viscoelastic Layers
p.111
Examination of Toughening Mechanisms of Zirconia Fabricated by Spark Plasma Sintering Methods
p.124
Fabrication of Metal Matrix Composites with Thermally Unstable Reinforcements by Spark Plasma Sintering
p.130

One-Pot Synthesis of 2-Phenylquinoline-4-Carboxylic Acid: Iron(III) Trifluoromethanesulfonate Catalysed Doebner Reaction

Article Preview

Abstract:

Iron (III) trifluoromethanesulfonate [Fe (OTF)3] has been proven to be an effective catalyst in the synthesis of 2-phenylquinoline-4-carboxylic acid by the Doebner reaction using one-pot pyruvic acid, aniline, and benzaldehyde. This method shows attractive characteristics including concise one-pot conditions, high atom economy, very limited energy consumption, and the sequential catalytic process requires only a catalytic (15 mol%) amount of Fe (OTf)3 with short reaction periods (3 h) . Meanwhile, the catalyst was easily recovered from the reaction system and reused smoothly with only a little loss of activity.

You might also be interested in these eBooks
Advanced Materials Science and Technologies II View Preview

Info:

Periodical:

Key Engineering Materials (Volume 907)

Pages:

97-102

DOI:

https://doi.org/10.4028/www.scientific.net/KEM.907.97

Citation:

Cite this paper

Online since:

January 2022

Authors:

Ayu Mutmainnah Halim, Antonius Herry Cahyana*, Rika Tri Yunarti

Keywords:

2-Phenylquinoline-4-Carboxylic Acid, Doebner Reaction, Iron (III) Trifluoromethanesulfonate, One-Pot Reaction

Export:

RIS, BibTeX

Price:

Permissions CCC:

Request Permissions

Permissions PLS:

Request Permissions

Сopyright:

© 2022 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

References

[1] B. Sureshkumar et al., Quinoline derivatives as possible lead compounds for anti-malarial drugs: Spectroscopic, DFT and MD study,, Arab. J. Chem., vol. 13, no. 1, hal. 632–648, (2020).

DOI: 10.1016/j.arabjc.2017.07.006

Google Scholar

[2] C. de la Guardia, D. E. Stephens, H. T. Dang, M. Quijada, O. V. Larionov, dan R. Lleonart, Antiviral activity of novel quinoline derivatives against dengue virus serotype 2,, Molecules, vol. 23, no. 3, hal. 1–11, (2018).

DOI: 10.3390/molecules23030672

Google Scholar

[3] J. Guillon et al., Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives,, J. Enzyme Inhib. Med. Chem., vol. 35, no. 1, hal. 432–459, (2020).

DOI: 10.1080/14756366.2019.1706502

Google Scholar

[4] A. G. Ribeiro et al., Novel 4-quinoline-thiosemicarbazone derivatives: Synthesis, antiproliferative activity, in vitro and in silico biomacromolecule interaction studies and topoisomerase inhibition,, Eur. J. Med. Chem., vol. 182, (2019).

Google Scholar

[5] M. F. El Shehry, M. M. Ghorab, S. Y. Abbas, E. A. Fayed, S. A. Shedid, dan Y. A. Ammar, Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents,, Eur. J. Med. Chem., vol. 143, hal. 1463–1473, (2018).

DOI: 10.1016/j.ejmech.2017.10.046

Google Scholar

[6] M. Taha et al., Synthesis of quinoline derivatives as diabetic II inhibitors and molecular docking studies,, Bioorganic Med. Chem., vol. 27, no. 18, hal. 4081–4088, (2019).

DOI: 10.1016/j.bmc.2019.07.035

Google Scholar

[7] A. Minić et al., Design and synthesis of novel ferrocene-quinoline conjugates and evaluation of their electrochemical and antiplasmodium properties,, Eur. J. Med. Chem., vol. 187, (2020).

Google Scholar

[8] G. A. Ramann dan B. J. Cowen, Recent advances in metal-free quinoline synthesis,, Molecules, vol. 21, no. 8, (2016).

DOI: 10.3390/molecules21080986

Google Scholar

[9] L. M. Nainwal et al., Green recipes to quinoline: A review,, Eur. J. Med. Chem., vol. 164, hal. 121–170, (2019).

Google Scholar

[10] C. L. Feng et al., Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate,, Chem. Pap., vol. 68, no. 8, hal. 1097–1103, (2014).

DOI: 10.2478/s11696-014-0544-8

Google Scholar

[11] C. Yao, B. Qin, H. Zhang, J. Lu, D. Wang, dan S. Tu, One-pot solvent-free synthesis of quinolines by C-H activation/C-C Bond formation catalyzed by recyclable iron(iii) triflate,, RSC Adv., vol. 2, no. 9, hal. 3759–3764, (2012).

DOI: 10.1039/c2ra20172k

Google Scholar

[12] S. Harikrishna, A. R. Robert, H. Ganja, S. Maddila, dan S. B. Jonnalagadda, A green, facile and recyclable Mn3O4/MWCNT nano-catalyst for the synthesis of quinolines via one-pot multicomponent reactions,, Sustain. Chem. Pharm., vol. 16, no. April, hal. 100265, (2020).

DOI: 10.1016/j.scp.2020.100265

Google Scholar

[13] R. Sandaroos, A. Nazif, H. Molaei, dan S. Salimi, Multicomponent synthesis of a new series of 4H-furo[3,4-b]pyrans, with iron(III) triflate as catalyst,, Res. Chem. Intermed., vol. 41, no. 8, hal. 5033–5040, (2015).

DOI: 10.1007/s11164-014-1585-x

Google Scholar