The Niementowski reaction of anthranilic acid with ethyl acetoacetate revisited: a new access to pyrano[3,2-c]quinoline-2,5-dione

Poronik, Yevgen M.; Klajn, Jan; Borzęcka, Wioleta; Gryko, Daniel T.

doi:10.3998/ark.5550190.p009.584

Cited by 3 publications

(1 citation statement)

References 6 publications

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“…[24] Synthesized quinoline hetero-cyclic compounds are synthesis has become a powerful for making new molecules for drug discovery and development [25] and other hands, quinoline derivatives owe their popularity since quinoline ring is quickly available synthetic approaches have been reported. [26,27] Although modern methods of Conrad-Limpach, [28] Niementowski, [29,30] Doebner-Miller, [31] Vilsmeier-Haak reactions [32] Claisen condensation reaction of amines with carboxyl derivative followed by cyclization to produce the desired quinolines molecule. [33] The classical multistep reaction operations, not only results in an increase in efficiency and but also reduces the generating large quantities of waste.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new 3‐(hydroxymethyl)‐2‐phenyl‐2,3 dihydroquinolinone and in‐silico evaluation of COVID‐19 main protease inhibitor

Nepolraj¹,

Shupeniuk

Sathiyaseelan³

et al. 2021

Vietnam Journal of Chemistry

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An exclusive approach towards the synthesis of novel 3‐(hydroxymethyl)‐2‐phenyl‐2,3 dihydroquinolin‐4(1H)‐one and it's in‐silico evaluation as inhibitor of COVID‐19 main protease. The one‐pot synthesis of an established procedure Claisen ester condensation reaction was sodium hydride mediated with intramolecular cyclization with solvent free conditions. The structures of the synthesized compound were confirmed by IR, 1H,13C NMR, and EI‐MS spectral studies. Chemo‐informatics study showed that the compound obeyed the Lipinski's rule, PASS, Swiss ADME. Computational docking analysis was performed using PyRx, AutoDock Vina option based on scoring functions. In‐silico molecular docking study results demonstrated Greater binding energy and affinity to the active pocket the N3 binding site of the Coronavirus primary protease.

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Section: Introductionmentioning

confidence: 99%

Synthesis of new 3‐(hydroxymethyl)‐2‐phenyl‐2,3 dihydroquinolinone and in‐silico evaluation of COVID‐19 main protease inhibitor

Nepolraj¹,

Shupeniuk

Sathiyaseelan³

et al. 2021

Vietnam Journal of Chemistry

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A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Yang,

Shi,

Wei

2024

Chemistry An Asian Journal

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In this paper, we have established an operationally convenient protocol for the rapid construction of polysubstituted methyleneindene and quinoline derivatives under mild conditions. This new synthetic method is achieved through the conversion of acetyl‐substituted methylenecyclopropanes with TsOH·H2O and ortho‐amino‐substituted methylenecyclopropanes with aromatic aldehyde and TsOH·H2O, respectively. A variety of transformations of the obtained products was demonstrated. The plausible reaction mechanisms were also proposed.

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Catalytic Syntheses of Pyrano[3,2-c]Quinolone and -Quinoline Derivatives and their Potential Therapeutic Agents

Aly,

Abd El-Naby,

Ahmed

et al. 2025

COC

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Pyrano[3,2-c]quinolone and pyrano[2,3-c]quinoline, as promising molecules, have garnered more attention due to their interesting biological properties. This review dealt with the catalytic synthesis of the former candidates in the last 20 years. Multi-component reactions (MCRs) are synthetic routes that produce a single product from three or more reactants in a one-pot step procedure. We herein reported on the advantages of catalysis in synthesizing the target compounds using the MCR sequence. We also discussed the mechanism and explained the chosen catalyst's utility in the target molecules' selectivity. Finally, this recent review focuses on the biological applications of these molecules as anticancer, antimicrobial activities, anti-diabetic, antiinflammatory, anti-Alzheimer, and antitubercular agents.

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The Niementowski reaction of anthranilic acid with ethyl acetoacetate revisited: a new access to pyrano[3,2-c]quinoline-2,5-dione

Cited by 3 publications

References 6 publications

Synthesis of new 3‐(hydroxymethyl)‐2‐phenyl‐2,3 dihydroquinolinone and in‐silico evaluation of COVID‐19 main protease inhibitor

Synthesis of new 3‐(hydroxymethyl)‐2‐phenyl‐2,3 dihydroquinolinone and in‐silico evaluation of COVID‐19 main protease inhibitor

A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Catalytic Syntheses of Pyrano[3,2-c]Quinolone and -Quinoline Derivatives and their Potential Therapeutic Agents

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