Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions

Panday, Anoop Kumar; Mishra, Richa; Jana, Asim Kumar; Parvin, Tasneem; Choudhury, Lokman H.

doi:10.1021/acs.joc.7b03272

Cited by 47 publications

(23 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to the reported works in the literature, the following insight regarding the mechanism (Scheme ) was attained. The catalyst abstracted the acidic proton of malononitrile to generate a carbanion, which attacked the carbonyl carbon to form Knoevenagel product ( 3 a ) with the elimination of water.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2019

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

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

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Parvin and Choudhury [ 29 ] developed a novel protocol for the creation of pyrimidine attached with quinolines employing a one‐pot C‐C and C‐N bond‐making approach. A prototype reaction was implemented reacting 6‐amino‐1,3‐dimethyluracil 67 and 2‐bromobenzaldehyde 68 using microwave power at 150°C and copper‐based catalyst and potassium carbonate as alkali as demonstrated in Scheme 22.…”

Section: Synthetic Strategiesmentioning

confidence: 99%

Microwave‐assisted diversified synthesis of pyrimidines: An overview

Kumar

2021

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Pyrimidines and their hybrid molecules have continued to be a favorable area for organic chemists owing to their richness in natural and synthetic compounds with multifarious involvement in pharmaceuticals and polymers and act as ligands. Different novel and greener synthetic protocols were developed in the last decades, but microwave‐assisted synthetic protocols played a significant role in constructing pyrimidine and its derivatives. In this article, we summarized the microwave‐supported strategy for the construction of pyrimidine fused or linked/tethered with other heterocycles, polysubstituted pyrimidines, solid‐supported synthesis of pyrimidines, and ionic liquid‐catalyzed strategies for the synthesis of pyrimidine and its derivatives reported in the last decade. Solid‐supported protocols using resins and ionic liquid‐catalyzed strategies afforded the corresponding products with excellent yield by dual activation. In most of the reports, the microwave‐irradiated approach was compared with conventional/traditional heating and found better in terms of reaction time, yield, atom economy, adherence with green chemistry principles, and reduction in purification wastage. Various authors evaluated the in vitro potential of synthesized pyrimidine derivatives for antimicrobial and antimalarial potential, and found moderate to excellent biological activity.

show abstract

“…In 1927, Koller’s group reported the synthesis of 1,8-naphthyridines for the first time . The improved Friedlander reactions use various catalysts, and organic solvents such as ligand-free copper catalyst in dimethylformamide (DMF), ruthenium nanolayer in mesitylene, Hf-UiO-66-N 2 H 3 metal–organic framework catalyst, trifluoroacetic acid in DMSO, and some recent advances can be found elsewhere . The studied catalysts and solvents used for the Friedlander reaction exhibit high cost, toxicity, high loading, low selectivity, high-temperature dependence, etc., which contribute to environmental pollution, limiting the criteria for green synthesis. , Thus, sustainable approaches need to be explored from a green perspective point of view, and a recent review sheds light on the greener synthesis of quinolone that uses water as the solvent .…”

Section: Introductionmentioning

confidence: 99%

Gram-Scale Synthesis of 1,8-Naphthyridines in Water: The Friedlander Reaction Revisited

et al. 2021

View full text Add to dashboard Cite

The products of the Friedlander reaction, i.e., 1,8-naphthyridines, have far-reaching impacts in materials science, chemical biology, and medicine. The reported synthetic methodologies elegantly orchestrate the diverse synthetic routes of naphthyridines but require harsh reaction conditions, organic solvents, and expensive metal catalysts. Here, we introduce gram-scale synthesis of 1,8-naphthyridines in water using an inexpensive and biocompatible ionic liquid (IL) as a catalyst. This is the first-ever report on the synthesis of naphthyridines in water. This is a one-step reaction, and the product separation is relatively easy. The choline hydroxide (ChOH) is used as a metal-free, nontoxic, and water-soluble catalyst. In comparison to other catalysts reported in the literature, ChOH has the advantage of forming an additional hydrogen bond with the reactants, which is the vital step for the reaction to happen in water. Density functional theory (DFT) and noncovalent interaction (NCI) plot index analysis provide the plausible reaction mechanism for the catalytic cycle and confirm that hydrogen bonds with the IL catalyst are pivotal to facilitate the reaction. Molecular docking and molecular dynamics (MD) simulations are also performed to demonstrate the potentialities of the newly synthesized products as drugs. Through MD simulations, it was established that the tetrahydropyrido derivative of naphthyridine (10j) binds to the active sites of the ts3 human serotonin transporter (hSERT) (PDB ID: 6AWO) without perturbing the secondary structure, suggesting that 10j can be a potential preclinical drug candidate for hSERT inhibition and depression treatment.

show abstract

Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions

Cited by 47 publications

References 42 publications

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

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

Microwave‐assisted diversified synthesis of pyrimidines: An overview

Gram-Scale Synthesis of 1,8-Naphthyridines in Water: The Friedlander Reaction Revisited

Contact Info

Product

Resources

About