Preparation and characterization of a novel DABCO‐based ionic liquid supported on Fe₃O₄@TiO₂ nanoparticles and investigation of its catalytic activity in the synthesis of quinazolinones

Abstract

In this study, quinazolinone derivatives have been synthesized via a suitable and efficient procedure by one‐potmulti‐component reactions of 3‐amino‐1,2,4‐triazole or 2‐aminobenzimidazole, dimedone and aromatic aldehydes in the presence of Fe3O4@TiO2‐IL as nanocatalyst under solvent‐free condition. The products were prepared in good to excellent yields using Fe3O4@TiO2‐IL magnetic nanocatalyst. The Fe3O4@TiO2 magnetic nanoparticles (MNPs) were prepared using beet juice extract and functionalized with IL based on DABCO. Moreover, the core‐shell structured magnetic Fe3O4@TiO2‐IL has been characterized by different techniques such as 1H‐NMR, FT‐IR, VSM, XRD, SEM, TGA, TEM and EDX. To the best of our knowledge, the prepared ionic liquid displayed a good protective and activator agent for magnetic nanocatalyst.

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

“…Several articles address different DABCO-based IL to promote similar three-component heterocyclizations; [127][128][129][130] the last article by Seyyedi et al also contains a comparison of the efficiency of DABCO-based IL (reaction times, yields, TON) with other types of catalysts in similar reactions, and the authors pointed out that their new catalysts have advantages in terms of simplicity of operation, high yields, formation of byproducts, and ease of processing because no column chromatography is required for isolation.…”

A Quick Access to Structurally Diverse Triazoloquinazoline Heterocycles via the MIL-101(Cr)-Catalyzed One-Pot Multi-Component Reaction of a Series of Benzaldehydes, Dimedone, and 1H-1,2,4-Triazol-3-Amine Under Green Conditions

“…Based on literature studies (Bakhshali-Dehkordi et al, 2020), herein, we assumed a possible mechanism for the one-pot multicomponent reaction of 1H-1,2,4-triazol-3-amine (1), benzaldehyde (2a), and dimedone (3) in the presence of MIL-101(Cr) as a novel catalyst (Scheme 1). According to the structure of MIL-101(Cr) reported in the literature, the active catalytic site of MIL-101(Cr) is conceivable, as shown in Figure 3 (Niknam et al, 2018).…”

“…Quinazolinone derivatives have been proven to exhibit interesting medicinal and therapeutical activities, including antitumor, antihypertensive, antifungal, analgesic and anti-inflammatory, antibacterial, antihistaminic, anticancer, antioxidant, and anti-HIV activities ( Karan et al, 2021 ). To the best of our knowledge, a few reports are available for the preparation of triazoloquinazolinones by condensation of 3,5-diamino-1,2,4-triazole, aromatic aldehydes, and dimedone ( Lipson et al, 2003 ; Heravi et al, 2008 ; Heravi et al, 2010 ; Krishnamurthy and Jagannath, 2013 ; Puligoundla et al, 2013 ; Mousavi and Maghsoodlou, 2015 ) such as H 6 P 2 W 18 O 62 •18H 2 O ( Heravi et al, 2008 ), microwave ( Krishnamurthy and Jagannath, 2013 ), molecular iodine (I 2 ) ( Puligoundla et al, 2013 ), refluxing in DMF ( Lipson et al, 2003 ), and more recently, TiO 2 nanoparticles supported ionic liquids ( Bakhshali-Dehkordi et al, 2020 ), Sc(OTf) 3 ( Gajaganti et al, 2018 ) and DABCO-based ionic liquid supported on Fe 3 O 4 @TiO 2 nanoparticles ( Bakhshali‐Dehkordi et al, 2020 ). Despite the usefulness of these catalysts, they also have some limitations, including high toxicity, use of expensive materials, complex synthetic processes, requirement of expensive and hazardous catalysts, and sometimes low yields.…”

Ionic liquid immobilized on modified magnetic FSM-16: an efficient and magnetically recoverable nanocatalyst

“…Therefore, magnetic mesoporous materials have attracted considerable attention as an attractive support for heterogeneous catalysts due to their superior properties such as environmentally benign nature, high stability, uniform porosity, easy separation, and recycling by applying a permanent magnet. 20–22…”