Series of Functionalized 5-(2-Arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1H,3H)-diones: A Water-Mediated Three-Component Catalyst-Free Protocol Revisited

Brahmachari, Goutam; Nayek, Nayana; Karmakar, Indrajit; Nurjamal, Khondekar; Chandra, Swapan K.; Bhowmick, Anindita

doi:10.1021/acs.joc.0c00732

Cited by 20 publications

(8 citation statements)

References 60 publications

(30 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To investigate the greenness and sustainability of the present protocol, a series of green metrics, − such as effective mass yield (EMY), atom economy (AE), atom efficiency (AEf), carbon efficiency (CE), reaction mass efficiency, optimum efficiency (OE), and E -factor, for the synthesized compounds were calculated (Supporting Information). The data show that this protocol provides high AE 88.15%–91.95% (for 4a–9d ) and 96.54%–96.73% (for 11a–c ) because only the water molecule is eliminated in this protocol.…”

Section: Results and Discussionmentioning

confidence: 99%

Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1H)-ones

et al. 2023

View full text Add to dashboard Cite

The current study deals with the synthesis and characterization of a novel catalyst made from diphenhydramine hydrochloride and CuCl ([HDPH]Cl−CuCl). The prepared catalyst was thoroughly characterized using various techniques, such as 1 H NMR, Fourier transform-infrared spectroscopy, differential scanning calorimetry, and thermogravimetric analysis and derivative thermogravimetry. More importantly, the observed hydrogen bond between the components was proven experimentally. The activity of this catalyst was checked in the preparation of some new derivatives of tetrahydrocinnolin-5(1H)ones via a multicomponent reaction between dimedone, aromatic aldehydes, and aryl/alkyl hydrazines in ethanol as a green solvent. Also, for the first time, this new homogeneous catalytic system was effectively used for the preparation of unsymmetric tetrahydrocinnolin-5(1H)-one derivatives as well as mono-and bis-tetrahydrocinnolin-5(1H)-ones from two different aryl aldehydes and dialdehydes, respectively. The effectiveness of this catalyst was further confirmed by the preparation of compounds containing both tetrahydrocinnolin-5(1H)one and benzimidazole moieties from dialdehydes. The one-pot operation, mild conditions, rapid reaction, and high atom economy, along with the recyclability and reusability of the catalyst, are other notable features of this approach.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1H)-ones

et al. 2023

View full text Add to dashboard Cite

show abstract

“…On the basis of inference revealed from the literature and resultant outcomes, , a plausible mechanistic pathway for the molecular iodine-catalyzed synthesis of imidazo[1,2- a ]pyridin-3-yl derivatives 4(a-o) is depicted in Scheme . The cascade reaction began with the attack of molecular iodine on acetophenone derivatives 2(a-g) in an aqueous medium followed by dehydration which resulted in situ generation of phenylglyoxal (1′ ) .…”

Section: Results and Discussionmentioning

confidence: 99%

“…On the basis of inference revealed from the literature and resultant outcomes, 41,42 a plausible mechanistic pathway for the molecular iodine-catalyzed synthesis of imidazo[1,2-a]pyridin- undergoes aza-Michael addition to form adduct (6), which subsequently undergoes intramolecular ring closure via an energetically favored 5-exo-trig process, thereby resulting in the cycloadduct (7) followed by removal of water that furnishes the desired product 4(a-o). The whole process involves the elimination of three molecules of water as a greener waste.…”

Section: Resultsmentioning

confidence: 99%

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

2022

View full text Add to dashboard Cite

The present paper discloses an ultrasonication strategy assisted by molecular iodine as an environmentally benign catalyst leading to the synthesis of pharmacologically significant imidazo[1,2- a ]pyridine scaffolds. The molecular-iodine-catalyzed approach for the synthesis of biologically active synthetic equivalents was achieved through three-component coupling embracing 2-aminopyridine derivatives, pertinent acetophenones, and dimedone in water medium under aerobic conditions. The higher product yield (up to 96%) with a miniature reaction time and modest catalyst loading as demonstrated by higher ecological compatibility and sustainability factors are fascinating features of this protocol. The structures of synthesized compounds were accomplished through FT-IR, 1 H NMR, 13 C NMR, mass, and elemental analysis data. The virtual screening of synthetic moieties was performed to ascertain the in silico selectivity and binding affinities against several biological targets. Lipinski’s rules of five, ADMET, and TOPKAT descriptors were used to evaluate the drug-likeness assets. Furthermore, a quantum computational study was computed at the B3LYP/6-311G++(d,p) level of theory to investigate the density functional theory-based chemical reactivity parameters and HOMO–LUMO energy gap of the synthesized derivatives. The present studies open the way for in vitro and in vivo testing of synthesized derivatives as potent inhibitors with an improved pharmacological profile against farnesyl diphosphate synthase, phosphodiesterase III, CXCR4, and GABAa receptor agonists.

show abstract

“…Brahmachari et al established an environmentally friendly method for synthesizing a novel series of functionalized pyrimidine derivatives [67]. This method involves a one-pot multicomponent reaction among arylglyoxal monohydrates, derivative of barbituric acid and 2-aminopyridines/2-aminopyrimidine under boiling water (Scheme 3) [67]. The author revealed that no catalyst/other additive was needed and avoided toxic organic solvents.…”

Section: Different Synthetic Strategies Of Pyrimidinesmentioning

confidence: 99%

A review on pyrimidine‐based derivatives: Synthesis and their biological application

Islam,

Akter

et al. 2024

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Pyrimidine‐based derivatives have attracted a lot of interest in heterocyclic chemistry due to its versatile structure and diverse biological activities. This study provides a comprehensive overview of synthetic strategy of different pyrimidine ring and highlights their biological importance. In this article, we start off by going through the fundamental procedures for the synthesis of pyrimidine scaffolds, including both conventional and contemporary synthetic techniques. These works cover a range of therapeutic domains, such as effects that are anticancer, antibacterial, antiviral, anti‐inflammatory, antioxidant, antimalarial, and so on. Moreover, we have summarized with a discussion of future prospects and challenges in the field of pyrimidine heterocyclic chemistry. This thorough review is a significant resource for researchers in medicinal chemistry and related fields since it offers insightful information about the synthetic methods and biological applications of pyrimidine‐based derivatives.

show abstract

Series of Functionalized 5-(2-Arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1H,3H)-diones: A Water-Mediated Three-Component Catalyst-Free Protocol Revisited

Cited by 20 publications

References 60 publications

Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1H)-ones

Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1H)-ones

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

A review on pyrimidine‐based derivatives: Synthesis and their biological application

Contact Info

Product

Resources

About