16285-33-9Relevant academic research and scientific papers
Palladium-Catalyzed Carbonylative Difunctionalization of C=N Bond of Azaarenes or Imines to Quinazolinones
Zhou, Xibing,Ding, Yongzheng,Huang, Hanmin
, p. 1678 - 1682 (2020/05/05)
Supporting information for this article is given via a link at the end of the document. By intercepting the acylpalladium species with C=N bond of azaarenes or imines other than free amines or alcohols, the difunctionalization of C=N bond was established via palladium-catalyzed carbonylation/nucleophilic addition sequence. This method is compatible with a diverse range of azaarenes and imines and allows for the efficient synthesis of a wide range of quinazolinones and derivatives. The synthetic utility has been demonstrated by one-step synthesis of evodiamine and its analogue with inexpensive starting materials.
Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by FeCl3/Al2O3 and analysis of large1H NMR diastereotopic effect
Monreal, Isabel,Sánchez-Castellanos, Mariano,Ramírez-Gualito, Karla,Cuevas, Gabriel,Espinoza, Karla A.,Rivero, Ignacio A.
, p. 124 - 131 (2018/12/13)
In the present study, we have carried out a condensation reaction for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-amino-N-benzylbenzamide and different aromatic aldehydes using FeCl3 catalyst supported on Al2O3. It was demonstrated that this material can be used successfully for the nucleation of quinazolinones with good to excellent yield; furthermore, the FeCl3/Al2O3 catalyst can be recovered and reused. This catalyst was used before in the synthesis of imidazole with very good yields. The synthesized quinazolinones showed a large range diastereotopic effect over the methylene group and, this anomalous difference was studied through nuclear magnetic resonance (NMR) and computational calculations.
Stable iridium(iv) complexes supported by tetradentate salen ligands. Synthesis, structures and reactivity
Lee, Chi Lun,Wu, Liangliang,Huang, Jie-Sheng,Che, Chi-Ming
supporting information, p. 3606 - 3609 (2019/03/26)
A series of trans-dichloroiridium(iv)-salen complexes were synthesized and structurally characterized by spectroscopic means and X-ray crystal structures. These Ir(iv) complexes are able to catalyze intramolecular C-H amination of aryl azides. The catalytic amination was drastically accelerated under microwave-assisted conditions, and possibly involves Ir-imido intermediates as supported by high-resolution ESI-MS analysis.
Synthesis, 2D-QSAR studies and biological evaluation of quinazoline derivatives as potent anti-trypanosoma cruzi agents
Battini, Leandro,Bollini, Mariela,Bruno, Ana M.,Casal, Juan J.,Lombardo, María E.,Ni?o, María E.,Puente, Vanesa R.,Sasiambarrena, Leandro D.,Valdez, Damián A. G.
, p. 265 - 276 (2019/07/12)
Background: Chagas disease affects about 7 million people worldwide. Only two drugs are currently available for the treatment for this parasite disease, namely, benznidazol (Bzn) and nifurtimox (Nfx). Both drugs have limited curative power in the chronic phase of the disease. Therefore, continuous research is an urgent need so as to discover novel therapeutic alternatives. Objective: The development of safer and more efficient therapeutic anti-T. cruzi drugs continues to be a major goal in trypanocidal chemotherapy. Method: Synthesis, 2D-QSAR and drug-like physicochemical properties of a set of quinazolinone and quinazoline derivatives were studied as trypanocidal agents. All compounds were screened in vitro against Trypanosoma cruzi (Tulahuen strain, Tul 2 stock) epimastigotes and bloodstream trypomastigotes. Results: Out of 34 compounds synthesized and tested, six compounds (5a, 5b, 9b, 9h, 13f and 13p) displayed significant activity against both epimastigotes and tripomastigotes, without exerting toxicity on Vero cells. Conclusion: The antiprotozoal activity of these quinazolinone and quinazoline derivatives represents an interesting starting point for a medicinal chemistry program aiming at the development of novel chemotherapies for Chagas disease.
A three-component process for the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives using nanosized nickel aluminate spinel crystals as highly efficient catalysts
Safaei-Ghomi, Javad,Teymuri, Raheleh
, (2019/07/15)
NiAl2O4 spinel nanocrystals were synthesized as mesoporous catalysts and were fully characterized using Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and Energy-dispersive X-ray spectroscopy (EDS). These nanocrystals catalyzed the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via a one-pot, three-component condensation reaction of aromatic aldehydes, isatoic anhydride, and ammonium acetate or primary aromatic amine under microwave irradiation. By far, the most obvious advantages of the offered process are efficiency and recyclability of the catalyst as well as a significantly shorter reaction time.
2,3-dihydro-4(1H)-quinazolinone compound as well as medicine composition and application thereof
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Paragraph 0074; 0079; 0080; 0081; 0082; 0083; 0084; 0085, (2019/04/11)
The invention relates to a 2,3-dihydro-4(1H)-quinazolinone compound as well as a medicine composition and application thereof. The 2,3-dihydro-4(1H)-quinazolinone compound has the main technical scheme that the structural general formula of the 2,3-dihydro-4(1H)-quinazolinone compound is shown as the formula (I) in the description; R1 is one of the following groups of hydrogen, methyl, methoxyl and halogen; R2 is one of the following groups of phenyl, a first group obtained by substituting at least one hydrogen in the phenyl by a substituent group, a pyridine group, a second group obtained bysubstituting at least one hydrogen in the pyridine group by a substituent group, a thiophene group, a furan group, saturated alicyclic hydrocarbon or first chain hydrocarbon; R3 is one of the following groups of phenyl, a third group obtained by substituting at least one hydrogen in the phenyl by a substituent group, a pyridine group, a thiophene group, a furan group, saturated alicyclic hydrocarbon and second chain hydrocarbon. The quinazolinone compound is mainly designed and synthesized; the compound can be used for preparing TRPC4 inhibitors or agonists, and preparing diabetes treatment medicine.
Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy
Gholap, Aniket V. A.,Maity, Soham,Schulzke, Carola,Maiti, Debabrata,Kapdi, Anant R.
, p. 7140 - 7146 (2017/09/07)
A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in air. The reaction also exhibits good functional group tolerance and would be of value to heterocyclic researchers as well as pharmaceutical process chemists. The reaction is proposed to proceed through a double SET type radical mechanism.
Crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes: A bio-nanoreactor with extremely high activity toward click-multi-component reactions
Shaabani, Ahmad,Afshari, Ronak,Hooshmand, Seyyed Emad
, p. 8469 - 8481 (2017/08/14)
In the present study, we have designed a procedure for the synthesis of a bio-nanoreactor catalyst, crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes (CS NPs/MWCNT@Fe3O4), via an in situ ionotropic gelation method. The synthesized robust nanoreactor was fully characterized. Moreover, the catalytic activity was investigated towards the click-based multi-component reactions for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, trisubstituted imidazoles, and 1,2,3-triazoles in a green medium. Since the nanocatalyst can be recovered by applying an external magnetic field, which results in easy separation without filtration, and recycled several times without the loss of its significant activities, it shows admirable potential in reusable catalysis.
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 (2017/06/27)
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.].
Synthesis and properties of 1,2-dihydro-4(3H)-quinazolinones
Khachatryan,Belus,Misyurin,Baryshnikova,Kolotaev,Matevosyan
, p. 1044 - 1058 (2017/10/31)
We modified the preparative-scale method for the synthesis of 2-aryl 1,2-dihydro-4(3H)-quinazolinone derivatives obtained in high yields by the reaction of new and commercially available aromatic aldehydes with anthranilic acid amides. A series of quinazolinone derivatives possessing anticancer and antiparasitic activities, as well as capable of preventing the progress of neurodegenerative diseases were characterized. There are grounds for clinical trials of these substances in order to select compounds being promising for clinical application.
