122022-10-0Relevant articles and documents
Magnetic Fe3O4 nanoparticles supported amine: a new, sustainable and environmentally benign catalyst for condensation reactions
Shiri, Lotfi,Kazemi, Mosstafa
, p. 4813 - 4832 (2017)
Abstract: Diethylenetriamine immobilized on magnetic Fe3O4 nanoparticles (DETA-Fe3O4) was successfully prepared as a new and well dispersed magnetically separable amine catalyst. The structure of the resulting catalyst was well characterized by a series of analysis techniques such as FT-IR, SEM, EDX, VSM, TGA and XRD. The catalytic activity of DETA-Fe3O4 was evaluated with Knoevenagel condensation of active methylene compounds with aromatic aldehydes. Interestingly, the cyclocondensation of anthranilamide and aldehydes were effectively catalyzed by DETA-Fe3O4 in water, and the desired products (2,3-dihydroquinazoline-4(1H)-ones) were afforded in admirable yields. Catalysis research under aqueous medium (water) also makes this synthetic protocol ideal and fascinating from the environmental point of view. The amine catalyst can be magnetically recovered after the reaction and can be reused many times without appreciable decrease in activity.
2,3-Dihydroquinazolin-4(1H)-one derivatives as potential non-peptidyl inhibitors of cathepsins B and H
Singh, Mamta,Raghav, Neera
, p. 12 - 22 (2015)
A direct correlation between cathepsin expression-cancer progression and elevated levels of cathepsins due to an imbalance in cellular inhibitors-cathepsins ratio in inflammatory diseases necessitates the work on the identification of potential inhibitors to cathepsins. In the present work we report the synthesis of some 2,3-dihydroquinazolin-4(1H)-ones followed by their evaluation as cysteine protease inhibitors in general and cathepsin B and cathepsin H inhibitors in particular. 2,3-Dihydroquinazolin-4(1H)-ones, synthesized by the condensation of anthranilamide and carbonyl compound in presence of PPA-SiO2 catalyst, were characterized by spectral analysis. The designed compounds were screened as inhibitors to proteolysis on endogenous protein substrates. Further, a distinct differential pattern of inhibition was obtained for cathepsins B and H. The inhibition was more to cathepsin B with Ki values in nanomolar range. However, cathepsin H was inhibited at micromolar concentration. Maximum inhibition was shown by compounds, 1e and 1f for cathepsin B and compounds 1c and 1f for cathepsin H. The synthesized compounds were established as reversible inhibitors of cathepsins B and H. The results were also compared with the energy of interaction between enzyme active site and compounds using iGemdock software.
The synthesis of 2,3-dihydroquinazolin-4(1H)-ones using zinc oxide nanotubes modified by SiO2 as a catalyst with recyclable effect
Hakimelahi, Rakhshan,Mousazadeh, Mohammad H.
, p. 86 - 92 (2018)
Zinc oxid nano tubes have attracted much attention in recent years. Hardly, direct uses of zinc oxid nano tubes which modified by SiO2 as a catalyst with recyclability has been applied for several organic reactions. The average particle size of
Copper(I) complex of 1,3-DimethylBarbituric acid modified SBA-15 and its catalytic role for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones and Imidazoles
Hajjami, Maryam,Ghorbani, Farshid,Yousofvand, Zakieh
, (2017)
An efficient one-pot method for synthesis of 2,3-dihydroquinazolin-4(1H)-ones and tri/tetra substituted-1H-imidazoles has been accomplished in the presence of catalytic amounts of Cu(I)-1,3-dimethylbarbituric acid modified SBA-15 as heterogeneous catalyst with good to excellent yields. The catalyst is reusable and can be applied several times without any decrease in product yield. The synthesized catalyst was characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), energy dispersive X-ray spectroscopy (EDS), thermal gravimetric analysis (TGA), N2 adsorption/desorption isotherms (BET), Fourier transform infrared spectroscopy (FT-IR) and atomic absorption spectroscopy (AAS).
One-pot B(C6F5)3 catalyzed cascade synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones
Shinde, Achut R.,Mane, Yogesh D.,Muley, Dnyanoba B.
, p. 33 - 40 (2020)
A new and efficient B(C6F5)3 catalyzed domino strategy has been developed for the synthesis of 2-substituted quinazolinones. The reaction utilizes 2-aminobenzamide and aldehydes for a one-pot protocol. A wide range of substrate scope, functional group tolerance, and operational simplicity with excellent yield are synthetically useful features.
Cu(II) complex-decorated hybrid nanomaterial: a retrievable catalyst for green synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Bodaghifard, Mohammad Ali,Safari, Somayeh
, p. 1613 - 1627 (2021/04/26)
The significant stability of magnetic core and ? OH functional groups on the surface of silica-coated cobalt ferrite (CoFe2O4@SiO2) nanoparticles make it a good candidate for functionalization and catalytic application. In
β-Cyclodextrin: A supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1 H)-one
Mitra, Bijeta,Chandra Pariyar, Gyan,Ghosh, Pranab
, p. 1271 - 1281 (2021/01/20)
β-Cyclodextrin, a green and widespread supramolecular catalyst, has been explored as a highly proficient promoter for the metal-free one-pot multi-component synthesis of a vast range of highly functionalized bioactive heterocyclic moiety, 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one, from easily available precursor aldehydes. The main endeavor of these protocols is to explore this organic supramolecule in one-pot multi-component synthesis. Absence of metal catalyst or toxic acid and harsh reaction conditions, excellent functional group tolerance, inexpensive, greener and environmentally safe protocol are the key advantages of this work.
Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions
Hajjami, Maryam,Sheikhaei, Shiva,Gholamian, Fatemeh,Yousofvand, Zakieh
, p. 2420 - 2435 (2021/01/04)
Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]
Mukaiyama's reagent promoted mild protocol for one-pot metal-free synthesis of dihydro quinazolinones
Rajput, Chatrasal S.,Srivastava, Shweta,Kumar, Ashish,Pathak, Arunendra
supporting information, (2021/01/25)
We have developed a fast and convenient method to prepare dihydroquinazolin-4(1H)-ones from anthranilamide and different aromatic aldehydes by using the Mukaiyama reagent. The reactions proceeded smoothly with a broad scope of substrates providing the expected products in good to excellent yields under with a low environmental factor and high atom economy. The metal-free condition and the ease of product isolation are the highlighted advantages in solving the issue of trace metal contamination in synthesized pharmaceuticals.
Confinement-Driven Enantioselectivity in 3D Porous Chiral Covalent Organic Frameworks
Hou, Bang,Yang, Shi,Yang, Kuiwei,Han, Xing,Tang, Xianhui,Liu, Yan,Jiang, Jianwen,Cui, Yong
supporting information, p. 6086 - 6093 (2021/02/01)
3D covalent organic frameworks (COFs) with well-defined porous channels are shown to be capable of inducing chiral molecular catalysts from non-enantioselective to highly enantioselective in catalyzing organic transformations. By condensations of a tetrahedral tetraamine and two linear dialdehydes derived from enantiopure 1,1′-binaphthol (BINOL), two chiral 3D COFs with a 9-fold or 11-fold interpenetrated diamondoid framework are prepared. Enhanced Br?nsted acidity was observed for the chiral BINOL units that are uniformly distributed within the tubular channels compared to the non-immobilized acids. This facilitates the Br?nsted acid catalysis of cyclocondensation of aldehydes and anthranilamides to produce 2,3-dihydroquinazolinones. DFT calculations show the COF catalyst provides preferential secondary interactions between the substrate and framework to induce enantioselectivities that are not achievable in homogeneous systems.
