63384-41-8Relevant academic research and scientific papers
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.
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
Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
Yang, Yang,Fu, Renzhong,Liu, Yang,Cai, Jing,Zeng, Xiaojun
, (2020/06/09)
A series of 2,3-dihydroquinazoline-4(1H)-one derivatives have been synthesized via one-pot three-component reaction using isatoic anhydrides, amines and aldehydes (or ketones) catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media and operational simplicity are the main highlights. Furthermore, the catalyst can be recovered and reused without evident loss of reactivity. This method provides a green and much improved protocol over the existing methods.
Corrigendum to “Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions” [Tetrahedron Lett. 76/27 (2020) 131312] (Tetrahedron (2020) 76(27), (S004040202030466X), (10.1016/j.tet.2020.131312))
Cai, Jing,Fu, Renzhong,Liu, Yang,Yang, Yang,Zeng, Xiaojun
, (2020/08/27)
The authors regret the following errors: 1. In page 1, “Additionally, 2,3-dihydroquinazolin-4(1H). -one derivatives can easily…” should be changed to “Additionally, 2,3-dihydroquinazolin-4(1H)-one derivatives can easily…” 2. In page 1, “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21], [?] [29] lewis acids [30–36],…” should be changed to “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21–29], lewis acids [30–36],…” 3. In page 1, “… alternative methods to perform organic. synthesis under environmentally benign conditions is in…” should be changed to “… alternative methods to perform organic synthesis under environmentally benign conditions is in…” 4. In page 2, “… condensation, which were. readily available based on our previous publicationsn…” should be changed to “… condensation, which were readily available based on our previous publications…” 5. In page 3, “… while bringing down the catalyst loading to 1 mol % led. to a reduction in the yield to…” should be changed to “… while bringing down the catalyst loading to 1 mol % led to a reduction in the yield to…” 6. In page 3, “… transformation to different substituted isatoic. anhydrides was performed.” should be changed to “… transformation to different substituted isatoic anhydrides was performed.” 7. In page 3, “… easily separated from the. reaction mixture via simple centrifugation…” should be changed to “… easily separated from the reaction mixture via simple centrifugation…” 8. The chemical structure 4a-4g should be changed in Table 2 as below: Table 2. HPAIL catalyzed three-component condensation of isatoic anhydrides, amines and aldehydes (or ketones).a [Figure presented] The authors would like to apologise for any inconvenience caused.
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 (2020/06/01)
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.
Organocatalytic combinatorial synthesis of quinazoline, quinoxaline and bis(indolyl)methanes
Badri, Rashid,Khaksar, Samad,Malamiri, Fatemeh,Tahanpesar, Elham
, p. 83 - 88 (2020/03/30)
Aims and Objective: An efficient and practical procedure for the synthesis of heterocyclic compounds such as quinazolines, quinoxalines and bis(indolyl)methanes was developed using 3,5-bis(trifluoromethyl) phenyl ammonium hexafluorophosphate (BFPHP) as a novel organocatalyst. Materials and Methods: All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. Result: Various products were obtained in good to excellent yields under reaction conditions Conclusion: The BFPHP organocatalyst demonstrates a novel class of non-asymmetric organocatalysts, which has gained much attention in green chemistry.
Synthesis of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones using CoAl2O4 nanoparticles as heterogeneous catalyst
Ahmadian, Fatemeh,Barmak, Alireza,Ghaderi, Esmali,Bavadi, Masoumeh,Raanaei, Hossein,Niknam, Khodabakhsh
, p. 2647 - 2658 (2019/07/17)
Abstract: The preparation and characterization of cobalt aluminate (CoAl2O4) magnetic nanoparticles and its application as a catalyst for the synthesis of a novel class of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones is described. The structure of the catalyst was studied by Fourier transform infrared spectroscopy, transmission electron microscopy, X-ray diffraction, and vibrating sample magnetometer analysis. The resulting cobalt aluminate (CoAl2O4) was an efficient catalyst and affords the desired products in good to excellent yields. Moreover, the catalyst could be easily recovered by magnetic separation and recycled for four times without significant loss of its catalytic activity. Graphic abstract: 2,3-Dihydroquinazolin-4(1H)-ones and a novel class of pyrazol-quinazolinones were synthesized through one-pot condensation reaction of isatoic anhydride, aromatic aldehydes, and amines using CoAl2O4 as nanoparticle heterogeneous catalyst in refluxing ethanol.[Figure not available: see fulltext.].
Metal-Free Oxidative C(sp 3)-N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones
Rezaei, Narjes,Sheikhi, Ehsan,Ranjbar, Parviz Rashidi
, p. 912 - 917 (2018/02/26)
A metal-free oxidative C(sp 3)-N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1 H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1 H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.
A process for preparing 2, 3 - antiviral properties - 4 (1 H) - one and its derivatives (by machine translation)
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Paragraph 0026-0027, (2017/08/26)
The invention discloses a method for preparing 2,3-dihydroquinazoline-4(1H)-one and a derivative thereof and belongs to the technical field of organic chemical synthesis. In the preparation, the mole ratio of isatoic anhydride to aromatic amine to aromati
