121998-76-3Relevant articles and documents
Supramolecular Fe3O4@PEG/?diaza crown ether@Ni: a novel magnetically reusable nano catalyst for the clean synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones
Aalinejad, Michael,Noroozi Pesyan, Nader,Heidari, Nosrat,Batmani, Hana,Danandeh Asl, Aria
, (2019)
Ni@diaza crown ether complex supported on magnetic nanoparticle was provided by grafting technique. The catalytic activity of Fe3O4@diaza crown ether@Ni was explored through one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones and it was used as an efficient and recoverably constant nanocatalyst. FT-IR, SEM, TEM, XRD, BET, ICP, EDS, and TGA techniques were employed to specify the nanocatalyst. This heterogeneous catalyst demonstrated acceptable recyclability and could be used again several times with no considerable loss of its catalytic activity.
The first report on the preparation of boehmite silica sulfuric acid and its applications in some multicomponent organic reactions
Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman
, p. 1205 - 1212 (2016)
Boehmite silica sulfuric acid (boehmite-SSA) has been prepared for the first time via an efficient sequential synthetic procedure. Initially, boehmite nanoparticles were prepared, coated by silica, and then reacted with chlorosulfonic acid to obtain boehmite-SSA. A simple, inexpensive, environmentally friendly and efficient procedure for the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives using this compound as an efficient and novel nanocatalyst has been described. Boehmite-SSA is a stable, heterogeneous, cost-effective, easy to handle, and recoverable catalyst and can be reused for several consecutive runs without a significant loss of catalytic activity. Its structure was characterized by FT-IR spectroscopy, thermogravimetric analysis (TGA), powder X-ray diffraction (XRD) and scanning electron microscopy (SEM).
A new concise synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives
Desroses, Matthieu,Scobie, Martin,Helleday, Thomas
, p. 3595 - 3597 (2013)
A new T3P-assisted, convenient and efficient procedure for the synthesis of dihydroquinazolinones is described. The main advantages of this protocol include its practical simplicity, short reaction times and particularly the ease with which products are isolated.
Inclusion complex of Isatoic anhydride with β-cyclodextrin and supramolecular one-pot synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in aqueous media
Patil, Dipak R.,Ingole, Pravin G.,Singh, Kripal,Dalal, Dipak S.
, p. 327 - 332 (2013)
The inclusion complex of isatoic anhydride with β-cyclodextrin was formed as a result of intermolecular interaction between isatoic anhydride with β-CD. The inclusion complex was confirmed by IR spectroscopy, X-ray diffraction and DSC studies. From application of complex, herein we have described a simple and efficient protocol for synthesis of 2, 3-dihydroquinazoline-4(1H)-one derivatives by one pot condensation of isatoic anhydride, ammonium acetate or amine and aldehyde using β-CD as a supramolecular catalyst in aqueous media.
Sulfated polyborate: mild, efficient and eco-friendly catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Khatri, Chetan K.,Patil, Manisha S.,Chaturbhuj, Ganesh U.
, p. 1683 - 1689 (2017)
Abstract: An efficient, inexpensive and recyclable sulfated polyborate catalyst was applied in a three-component, one-pot cyclocondensation of isatoic anhydride, aldehydes and ammonium acetate/amines to afford the corresponding 2,3-dihydroquinazolin-4(1H)-ones. The key advantages of the present method are high yields, short reaction time, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards. Graphical Abstract: [Figure not available: see fulltext.].
A Highly Stereocontrolled, One-Pot Approach toward Pyrrolobenzoxazinones and Pyrroloquinazolinones through a Lewis Acid-Catalyzed [3 + 2]-Cycloannulation Process
Boomhoff, Michael,Ukis, Rostyslav,Schneider, Christoph
, p. 8236 - 8244 (2015)
We report herein a stereocontrolled [3 + 2]-cycloheteroannulation of bis-silyl dienediolate 1 with 2-aminobenzoic acid- and 2-aminobenzamide-derived imines to furnish highly substituted pyrrolo[1,2-a]benzoxazinones 3 and pyrrolo[1,2-a]quinazolinones 4, respectively, in good overall yields. This one-pot process rapidly generates molecular complexity and comprises a Lewis acid-catalyzed, vinylogous Mannich reaction of 1 followed by an intramolecular N,O-acetal- and N,N-aminal formation, respectively, which proceeds with good to excellent stereocontrol.
Organic-inorganic hybrid polyoxometalate and its graphene oxide-Fe3O4 nanocomposite, synthesis, characterization and their applications as nanocatalysts for the Knoevenagel condensation and the synthesis of 2,3-dihydroquinazolin-4(1: H)-ones
Khoshnavazi, Roushan,Bahrami, Leila,Havasi, Forugh
, p. 100962 - 100975 (2016)
The simple and high yield synthesis of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O (PPD = p-phenylenediamine) as a new organic-inorganic hybrid polyoxometalate is reported. The new compound consists of trimetal-substitution polyoxometalate of A-β-SiW9Cu3O3710-, water molecules and coordinated and noncoordinated PPD molecules. H6Cu2[PPD]6[SiW9Cu3O37]·12H2O was firmly grafted on graphene oxide decorated with Fe3O4 nanoparticles. These nanocomposites were characterized by elemental analyses, thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), X-ray photoelectron spectrum (XPS), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), and alternating gradient force magnetometer (AGFM). The results indicate that the size range of the nanoparticles are between 20 and 60 nm. The catalytic activity of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O and the magnetically reusable nanocomposite of GO@Fe3O4@H6Cu2[PPD]6[SiW9Cu3O37]·12H2O were investigated in the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-ones.
A novel magnetic nanocatalyst Fe3O4@PEG–Ni for the green synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Noroozi Pesyan, Nader,Danandeh Asl, Aria,Namdar, Shadi
, (2020)
Ni-PEG (polyethylene glycol) complex supported on magnetic nanoparticle was created by grafting. The catalytic activity of Fe3O4@PEG–Ni was explored through one-pot green synthesis of 2,3-dihydroquinazolin-4(1H)-ones and used as an efficient and recoverable nanocatalyst. FT-IR, XRD, EDS, BET, TGA, VSM and SEM techniques were employed to specify the nanocatalyst. This heterogeneous nanocatalyst demonstrated acceptable recyclability and could be reused several times with no considerable loss of its catalytic activity.
A one-pot synthesis of 2-aryl-2,3-dihydro-4(1H)-quinazolinones by use of samarium iodide
Cai, Guoping,Xu, Xiaoliang,Li, Zhifang,Weber, William P.,Lu, Ping
, p. 1271 - 1272 (2002)
2-Aryl-2,3-dihydro-4(1H)-quinazolines have been prepared in a one-pot synthesis by samarium idoide (SmI2) promoted reaction of o-nitrobenzamide and aldehydes.
Benzene-1,3,5-tricarboxylic acid-functionalized MCM-41 as a novel and recoverable hybrid catalyst for expeditious and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones via one-pot three-component reaction
Nikooei, Niusha,Dekamin, Mohammad G.,Valiey, Ehsan
, p. 3891 - 3909 (2020)
Benzene-1,3,5-tricarboxylic acid-functionalized MCM-41 (MCM-41-Pr-BTA), as a novel hybrid organosilica, was prepared and properly characterized by the Fourier-transform infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy, Brunauer–Emmett–Teller, thermal gravimetric analysis and energy-dispersive X-ray spectroscopy to evaluate the functional groups, crystallinity, surface area, morphology, particle size distribution and loading of functional groups. Interestingly, the 1,3-propylene linker used in this study incorporates appropriate catalytic activity into the MCM-41 framework compared to the more known trialkoxypropyl silanes. This new organosilica can be used as a hybrid nanocatalyst for the expeditious and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives, as an important pharmaceutical scaffold, in aqueous media via a three-component one-pot condensation of isatoic anhydride and aromatic aldehydes with primary amines or ammonium salts. This method has several advantages such as low catalyst loading, high to excellent yields, short reaction times, working under green conditions and simple workup.
An efficient one pot-three component cyclocondensation in the synthesis of 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones: Potential antitumor agents
Roopan, Selvaraj Mohana,Nawaz Khan,Jin, Jong Sung,Senthil Kumar
, p. 919 - 927 (2011)
Montmorillonite K10 efficiently catalyzed a one pot-three component cyclocondensation of isatoic anhydride, NH4OAc and aromatic/heteroaromatic aldehydes under ambient conditions to produce the corresponding 2-substituted-2,3-dihydroquinazolin-4(1H)-ones in good yields. The 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones 3a-d were screened for their antitumor activity against Ehrlich Ascites Carcinoma tumor cells
Anchoring of Cu–dimethylglyoxime complex in MCM-41 matrix: a new, recyclable, and highly efficient nanocatalyst for the green preparation of 2,3-dihydroquinazolin-4(1H)-ones
Hassanloie, Nishtman,Noroozi Pesyan, Nader,Ojaghi Aghbash, Khadijeh,Sheykhaghaei, Golaleh
, p. 833 - 844 (2021)
A new heterogeneous nanocatalyst containing Cu–dimethylglyoxime complex grafted to an MCM-41 matrix was synthesized. This recoverable nanocomposite was applied as a highly effective, green, thermally stable catalyst in the one-pot reductive cyclization of aromatic aldehydes with 2-aminobenzamide. 2,3-Dihydroquinazolin-4(1H)-ones were obtained in 80–98% yield. The MCM-41-silylcyclopropyl-dimethylglyoxime-Cu heterogeneous nanocomposite was well identified using X‐ray diffraction, field emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy‐dispersive X‐ray spectroscopy, Brunauer–Emmett–Teller technique, and thermogravimetric analysis. The eco-friendly nanocatalyst demonstrated excellent recyclability: it could be reused for at least six successive cycles without any notable decrease in its catalytic function. Graphic abstract: [Figure not available: see fulltext.]
An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols
Dong, Yibo,Wu, Yangjie,Yan, Congcong,Yang, Jinchen,Zhang, Jinli
, p. 15344 - 15349 (2021/09/07)
An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.
Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst
Thorve, Pradip Ramdas,Maji, Biplab
, p. 1116 - 1124 (2021/02/26)
Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.
