Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation

Rahmati, Mohammad Hossein; Habibi, Davood

doi:10.1007/s11164-020-04361-y

Cited by 11 publications

(5 citation statements)

References 81 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

“…5 DESs are often cheap and safe and are usually formed by mixing two or three ionic compounds each component has a high melting point, but when they are combined, the melting point of the prepared DES is lower than that of each component. [6][7][8] DESs have countless advantages over conventional solvents, as they not only comply with the principles of green chemistry but also act as catalysts, depending on their properties .…”

Section: Introductionmentioning

confidence: 99%

The new phthalic acid-based DES as a versatile catalyst for the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromenes

Monem,

Habibi,

Alizadeh

et al. 2024

Preprint

Self Cite

View full text Add to dashboard Cite

Deep eutectic solvents (DESs) have found many applications in recent years and with countless advantages over regular solvents, not only complying with green chemistry principles but also acting as catalysts depending on their properties. In this regard, a new DES (MTPPBr-PHTH-DES) was prepared from a mixture (molar ratio 1:1) of methyltriphenylphosphonium bromide (MTPPBr) and phthalic acid (PHTH), characterized with various techniques such as FT-IR, TGA/DTA, densitometer, eutectic point, and 1H NMR and used as an acid catalyst in the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromes in solvent-free conditions. Short reaction time, high efficiency, and easy recycling and separation of the DES catalyst are among the most important features of the presented method.

show abstract

“…DESs have been developed in line with the goals of green chemistry as a suitable alternative to ionic liquids (ILs) and have found many applications in various research fields [ 5 ]. DESs are often cheap and safe and usually consist of mixing two or three ionic compounds where each component has a high melting point, but when they are combined, the melting point of the prepared DES is lower than either component [ 6 – 8 ]. DESs have countless advantages over conventional solvents, as they not only comply with the principles of green chemistry but also act as catalysts, depending on their properties and they do not need to be separated and purified.…”

Section: Introductionmentioning

confidence: 99%

The new phthalic acid-based deep eutectic solvent as a versatile catalyst for the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromenes

Monem,

Habibi,

Alizadeh

et al. 2024

BMC Chemistry

Self Cite

View full text Add to dashboard Cite

A new DES (MTPPBr-PHTH-DES) was prepared from a mixture of methyltriphenyl-phosphonium bromide (MTPPBr) and phthalic acid (PHTH). The eutectic point phase diagram showed that a one-to-one molar ratio of MTPPBr to PHTH is the optimal molar ratio for the synthesis of new DES. Then, it was characterized with various techniques such as FT-IR, TGA/DTA, densitometer, eutectic point, and NMR and used as a novel acid catalyst in the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromes in solvent-free condition. Short reaction time, low temperature, high efficiency, green condition, and easy recycling and separation of the DES catalyst are among the most important features of the presented method.

show abstract

Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation

Cited by 11 publications

References 81 publications

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

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

The new phthalic acid-based DES as a versatile catalyst for the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromenes

The new phthalic acid-based deep eutectic solvent as a versatile catalyst for the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromenes

Contact Info

Product

Resources

About

Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation

Cited by 11 publications

References 81 publications

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

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

The new phthalic acid-based DES as a versatile catalyst for the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromenes

The new phthalic acid-based deep eutectic solvent as a versatile catalyst for the synthesis of pyrimido[4,5-d]pyrimidines and pyrano[3,2-c]chromenes

Contact Info

Product

Resources

About

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

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