Amino Acid Catalyzed Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives

Mustaque, K. Mohammed; Subramani, A.; Shabeer, T. K.; Thajudeen, Habeebullah; Ahamed, V.S. Jamal

doi:10.2174/1570178614666171130154814

Cited by 7 publications

(1 citation statement)

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“…Therefore, Nemours synthesis approaches have been developed for the synthesis of DHQZs. The most commonly used methods for the preparation of DHQZs include the condensation of aldehydes or ketones with anthranilamide or the three-component condensation of aldehydes, isatoic anhydride, and amines utilizing catalysts such as montmorillonite K-10 [22], Perchlorated Zirconia (HClO4/ZrO2) [23], Amino Acid [24], Nano-MgO [25] [29]. Also, some researchers used sulfonic acid-functionalized mesoporous silica catalyst for the synthesis of DHQZs.…”

Section: Introductionmentioning

confidence: 99%

KCC-1/Pr-SO₃H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

2020

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KCC-1/Pr-SO3H is found to be a considerable efficient nanocatalyst for the one-pot threecomponent condensation coupling of aromatic aldehydes, isatoic anhydride, and primary amines for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ethanol as a green solvent under reflux conditions with excellent yields. The influence of different reaction parameters such as the effects of solvent, temperature, time, and concentration of catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-one (4f) were studied. KCC-1/Pr-SO3H is easily recyclable without the significant loss of catalytic activities after seven times. This mild and simple synthesis method offers some worthwhile advantages including short reaction time, high yield, and convenient work-up procedure.

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Section: Introductionmentioning

confidence: 99%

KCC-1/Pr-SO₃H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

2020

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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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Synthetic approaches toward 2,3-dihydroquinazolinones (microreview)

Mohideen,

Shabeer

2023

Chem Heterocycl Comp

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Amino Acid Catalyzed Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives

Cited by 7 publications

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KCC-1/Pr-SO₃H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

KCC-1/Pr-SO₃H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

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

Synthetic approaches toward 2,3-dihydroquinazolinones (microreview)

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Amino Acid Catalyzed Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives

Cited by 7 publications

References 0 publications

KCC-1/Pr-SO3H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

KCC-1/Pr-SO3H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

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

Synthetic approaches toward 2,3-dihydroquinazolinones (microreview)

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KCC-1/Pr-SO₃H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

KCC-1/Pr-SO₃H: an efficient heterogeneous catalyst for green and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one

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