Cholinesulfuric acid ionic liquid catalyzed an eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-one in aqueous media

Azizi, Najmedin; Shirdel, Fatemeh

doi:10.1007/s11164-016-2849-4

Res Chem Intermed

2017

DOI: 10.1007/s11164-016-2849-4

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Cholinesulfuric acid ionic liquid catalyzed an eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-one in aqueous media

Najmedin Azizi

Fatemeh Shirdel

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2024

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Cited by 10 publications

References 48 publications

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An eco‐friendly, sustainable, and greener approach to the synthesis of Dihydroquinazolin‐4(1H)‐ones using a deep eutectic solvent

Kumar,

Seboletswe,

Manhas

et al. 2023

Journal of Heterocyclic Chem

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A safer, greener, and more effective reaction methodology for the synthesis of dihydroquinazolinones (DHQs) has been developed. The deep eutectic solvent (DES) ZnCl2/urea employed in this study efficiently accelerated the cyclization of 2‐aminobenzamide with different aldehydes (aromatic and heteroaromatic) to afford the target scaffolds without the generation of any oxidized product. This method has exhibited remarkable advantages such as quick reaction time, mild reaction conditions, high yield (82%–98%), operational simplicity, and selectivity. The approach was observed to be tolerant to electron‐donating and electron‐withdrawing functional groups. Green metric parameters (AEf, OE, AE, RME, CE, etc.) determined further aided this greener chemical approach.

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An eco‐friendly, sustainable, and greener approach to the synthesis of Dihydroquinazolin‐4(1H)‐ones using a deep eutectic solvent

Kumar,

Seboletswe,

Manhas

et al. 2023

Journal of Heterocyclic Chem

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1,10‐Phenanthroline‐Based Molten Salt as a Bifunctional Sulfonic Acid Catalyst: Application to the Synthesis of N‐Heterocycle Compounds via Anomeric Based Oxidation

et al. 2018

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1,10‐phenanthroline‐based molten salt as a bifunctional sulfonic acid [Phen(SO3H)2]Cl2 was designed and synthesized. The described nano molten salt has two SO3H acid groups and a rigid structure that allows the rotation of the molecule to have a unique catalytic ability. This catalyst was applied for the synthesis of N‐heterocyclic compounds such as quinazolines, quinazolinones, acridines and dihydropyridines via multi‐component condensation reactions. These compounds are highly regarded for their medicinal and biological properties. The effect of different functional groups at the corresponding products for developing the new mechanisem entitled “anomeric based oxidation” (ABO) were studied. The major advantages of the presented methodology are mild conditions, high efficiency, short reaction times and reusability of the catalyst.

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C₁₈‐DABCO‐AA: A Novel Brønsted Acidic Gemini Surfactant for the Environmental Benign Synthesis of 2,3‑Dihydroquinazolin‑4(1H)‑ones in Water at Ambient Temperature

Rajmane,

Shirke,

Sutar

et al. 2024

ChemistrySelect

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We have successfully synthesized a new acidic surfactant named C18‐DABCO‐AA, which contains octadecyl and acetic acid substituent on DABCO (1,4‐diazabicyclo [2.2.2] octane) unit, with an excellent yield. The synthesized surfactant was analyzed using FT‐IR, 1H NMR, and 13C NMR spectroscopic techniques. Its thermal behavior was analyzed by using the TGA–DTA technique. Our analysis indicates that the synthesized surfactant has excellent surfactant properties. Its critical micelle concentration (CMC) is 0.80 mM as determined by the conductivity method and UV–vis absorption measurement at 298.15 K. Surfactant also showed strong acidic properties with a pKa of 3.3. It is the best catalyst for the synthesis of 2,3‑dihydroquinazolin‑4(1H)‐ones (DHQs) in water at 40 °C. The synthesis is achieved via two‐component reactions of various aromatic aldehydes and anthranilamide in water at a CMC concentration of C18‐DABCO‐AA. The method was also extended for synthesizing DHQs via two‐component reactions of different ketones and anthranilamide under similar reaction conditions. The products were achieved in with yields ranging from good to excellent within 60–90 min. Additionally, the aqueous solution with C18‐DABCO‐AA was reused up to five times with a minor decrease in product yield. The present protocol is fast, energy‐efficient, and can be used on a large scale for synthetic purposes. Additionally, it boasts impressive environmentally friendly credentials.

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Cholinesulfuric acid ionic liquid catalyzed an eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-one in aqueous media

Cited by 10 publications

References 48 publications

An eco‐friendly, sustainable, and greener approach to the synthesis of Dihydroquinazolin‐4(1H)‐ones using a deep eutectic solvent

An eco‐friendly, sustainable, and greener approach to the synthesis of Dihydroquinazolin‐4(1H)‐ones using a deep eutectic solvent

1,10‐Phenanthroline‐Based Molten Salt as a Bifunctional Sulfonic Acid Catalyst: Application to the Synthesis of N‐Heterocycle Compounds via Anomeric Based Oxidation

C₁₈‐DABCO‐AA: A Novel Brønsted Acidic Gemini Surfactant for the Environmental Benign Synthesis of 2,3‑Dihydroquinazolin‑4(1H)‑ones in Water at Ambient Temperature

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Cholinesulfuric acid ionic liquid catalyzed an eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-one in aqueous media

Cited by 10 publications

References 48 publications

An eco‐friendly, sustainable, and greener approach to the synthesis of Dihydroquinazolin‐4(1H)‐ones using a deep eutectic solvent

An eco‐friendly, sustainable, and greener approach to the synthesis of Dihydroquinazolin‐4(1H)‐ones using a deep eutectic solvent

1,10‐Phenanthroline‐Based Molten Salt as a Bifunctional Sulfonic Acid Catalyst: Application to the Synthesis of N‐Heterocycle Compounds via Anomeric Based Oxidation

C18‐DABCO‐AA: A Novel Brønsted Acidic Gemini Surfactant for the Environmental Benign Synthesis of 2,3‑Dihydroquinazolin‑4(1H)‑ones in Water at Ambient Temperature

Contact Info

Product

Resources

About

C₁₈‐DABCO‐AA: A Novel Brønsted Acidic Gemini Surfactant for the Environmental Benign Synthesis of 2,3‑Dihydroquinazolin‑4(1H)‑ones in Water at Ambient Temperature