Synthesis of Bis-2,3-dihydroquinazolin-4(1H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones Derivatives with the Aid of Silica-Supported Preyssler Nanoparticles

Abstract

One-pot three-component condensation of isatoic anhydride with primary amines or ammonium carbonate and aromatic aldehydes in refluxing ethanol in the presence of catalytic amounts of silica-supported preyssler nanoparticles (SPNP) afforded the corresponding 2,3-dihydroquinazolin-4(1H)-ones in high yields, and bis-dihydroquinazolinones were synthesized for the first time by a novel pseudo-five-component condensation of isatoic anhydride, a primary amine, and a dialdehyde in water. The catalyst is reusable and can be applied several times without any decrease in product yield.

2,3-Dihydroquinazolin-4(1H)-one as a privileged scaffold in drug design

“…94 The integration of mesoporous silica with magnetic NPs is certainly of great interest for practical applications. As shown in Table 3, different silica-supported NPs were used as catalysts for the one-pot three-component reaction, leading to 45-97% yield in 1-8 h. [95][96][97][98][99] The use of solid acids, as non-toxic, low-cost and reusable catalysts, has also emerged in the synthesis of DHQs (Table 3). Among them, several acids bearing sulfonic moiety supported on silica catalyzed the multi-component synthesis under different conditions, providing DHQs with >70% yield in 0.5-7 h. [100][101][102][103][104] MCM-41 is another type of ordered mesoporous silica material.…”

Eco-Friendly Synthesis of Bioactive Heterocycles

“…We believe that the present methodology addresses the current drive toward green chemistry due to high yields, atomic economy, and reusability of the catalyst. By the reaction of a range of amines and dialdehydes, novel libraries of bisdihydroquinazolinones could be obtained, which would make this method a suitable candidate for combinatorial and parallel synthesis in drug discovery [107] (Schemes 3.48, 3.49, and 3.50). -dione derivatives via one-pot reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine, arylaldehydes, and 2-hydroxynaphthalene-1,4-dione in water as green solvent and using cerium oxide nanoparticles (CONPs) as a heterogeneous catalyst.…”

BF3‐grafted Fe3O4@Sucrose nanoparticles as a highly‐efficient acid catalyst for syntheses of Dihydroquinazolinones (DHQZs) and Bis 3‐Indolyl Methanes (BIMs)

“…Recently, 2,3‐ Dihydroquinazolin‐4(1H)‐ones stimulated extensive interest for their anticonvulsant, antiparkinsonian, antihypertensive, antibacterial, anticancer, diuretic, as well as monoamine oxidase inhibition and plant growth regulation . There are numerous classical synthetic methods for synthesizing such important compounds using various acids as catalyst like MCM‐41‐Ni coordinated mesoporous, GO nanosheets, Fe 3 O 4 ‐GO and also preliminary endeavors; TiCl 4 ‐Zn, Sc(OTf) 3 , NH 4 Cl, I 2 /KI and solvent as an oxidant, VO(acac) 2 ‐oxidizer, heteropolyacids and T3P™ . In deeper surveys, it is revealed that enantioselective additives also have had an important place for an investigation .…”