β-Cyclodextrin: a supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1<i>H</i>)-one

Mitra, Bijeta; Pariyar, Gyan Chandra; Ghosh, Pranab

doi:10.1039/d0ra09562a

Cited by 22 publications

(7 citation statements)

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“…This ). [145] The reaction is promoted by the free primary -OH groups of the β-cyclodextrin which activates both the aldehyde 1 and acetophenone derivatives 18 as the active electrophile species. The reaction of malononitrile and ammonium acetate with these two activated electrophiles followed by a sequence of tautomerization, and cyclization generates the desired product 626.…”

Section: Synthesis Of Quinazolinesmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Section: Synthesis Of Quinazolinesmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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“…Malononitrile (0.12 ml; 2.16 mmol) was added to a solution of compound 3 (0.33 g; 1.584 mmol) in EtOH (4 ml) containing excess ammonium acetate (Mitra et al, 2021;Rahmati & Habibi, 2021;Sayahi et al, 2019;Tamaddon & Tadayonfar, 2020;Zolfigol et al, 2016). The reaction flask was covered with foil and the mixture mechanically stirred under reflux at 50-60°C.…”

Section: -(34-dichlorophenyl)-4-phenyl-23-dihydro-1h-15benzodiazepine...mentioning

confidence: 99%

Chalcone‐inspired rA₁/A_2A adenosine receptor ligands: Ring closure as an alternative to a reactive substructure

et al. 2021

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Over the past few years, great progress has been made in the development of high-affinity adenosine A 1 and/or A 2A receptor antagonists-promising agents for the potential treatment of Parkinson's disease. Unfortunately, many of these compounds raise structure-related concerns. The present study investigated the effect of ring closures on the rA 1 /A 2A affinity of compounds containing a highly reactive α,βunsaturated carbonyl system, hence providing insight into the potential of heterocycles to address these concerns. A total of 12 heterocyclic compounds were synthesised and evaluated in silico and in vitro. The test compounds performed well upon qualitative assessment of drug-likeness and were generally found to be free from potentially problematic fragments. Most also showed low/ weak cytotoxicity. Results from radioligand binding experiments confirm that heterocycles (particularly 2-substituted 3-cyanopyridines) can replace the promiscuous α,βunsaturated ketone functional group without compromising A 1 / A 2A affinity. Structure-activity relationships highlighted the importance of hydrogen bonds in binding to the receptors of interest. Compounds 3c (rA 1 K i = 16 nM; rA 2A K i = 65 nM) and 8a (rA 1 K i = 102 nM; rA 2A K i = 37 nM), which both act as A 1 antagonists, showed significant dual A 1 /A 2A affinity and may, therefore, inspire further investigation into heterocycles as potentially safe and potent adenosine receptor antagonists.

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“…They offer several advantages over other host molecules, including wide availability from renewable sources, good water solubility, biocompatibility and simplicity in chemical modification. Their molecular recognition of guest molecules is also well recognized [2]. These "molecules of holes" have lately gained favour as building blocks for the self-assembly of supramolecular structures with varied porosity [3].…”

Section: Introductionmentioning

confidence: 99%

In silico and in vitro study of pyrimidones synthesized with ethylenediamine- modified β-cyclodextrin: potential against ESBL E. coli

Rajapriyan,

Masood Khan,

Khan R.

et al. 2024

Bull. Chem. Soc. Eth.

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Modern organic synthesis is primarily focused on developing environmentally benign synthetic protocols by employing green chemistry principles. Accordingly, in our recent research work, we herein report the use of modified supramolecular host cyclodextrin as an effective solid based green catalyst for accessing structurally diverse and medicinally relevant pyrimidone architectures. The catalyst and the synthesized compounds 4 (a-r) were characterized using FT-IR, NMR and GC-mass spectroscopy. Major highlights of the reported work include the economical atom process, remarkably gentler reaction conditions, ease of operation, high isolated yields, and excellent catalyst turnover numbers. The molecular docking studies suggest that the compound 4n has hydrogen bonding, hydrophobic and π-pair interactions with the active site of the CXT M 15 receptor. Further, the in-vitro antibacterial study as well as the screening of anti-biofilm activity resulted in a BIC value of 76.79 ± 0.785% at a concentration of 10 µg/mL and morphological alterations induced by DHPMs against the ESBL E. coli strain aggregated with a good result. KEY WORDS: Ethylenediamine modified β-CD, Multicomponent reaction, 3,4-dihydropyrimidin-2(1H)-ones DHPM derivatives, Solvent-free conditions, Reusability, Antibactercidal Bull. Chem. Soc. Ethiop. 2024, 38(4), 1103-1118. DOI: https://dx.doi.org/10.4314/bcse.v38i4.23

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β-Cyclodextrin: a supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one

Abstract: A vast range of 2-amino-4,6-diphenylnicotinonitrile and 2,3-dihydroquinazolin-4(1H)-one were synthesized through a metal-free one-pot multi-component synthesis using β-cyclodextrin as an efficient supramolecular organocatalyst.

Cited by 22 publications

References 93 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Chalcone‐inspired rA₁/A_2A adenosine receptor ligands: Ring closure as an alternative to a reactive substructure

In silico and in vitro study of pyrimidones synthesized with ethylenediamine- modified β-cyclodextrin: potential against ESBL E. coli

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β-Cyclodextrin: a supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one

Abstract: A vast range of 2-amino-4,6-diphenylnicotinonitrile and 2,3-dihydroquinazolin-4(1H)-one were synthesized through a metal-free one-pot multi-component synthesis using β-cyclodextrin as an efficient supramolecular organocatalyst.

Cited by 22 publications

References 93 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Chalcone‐inspired rA1/A2A adenosine receptor ligands: Ring closure as an alternative to a reactive substructure

In silico and in vitro study of pyrimidones synthesized with ethylenediamine- modified β-cyclodextrin: potential against ESBL E. coli

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Chalcone‐inspired rA₁/A_2A adenosine receptor ligands: Ring closure as an alternative to a reactive substructure