17519-06-1Relevant academic research and scientific papers
Silica-supported sodium hydrogen sulfate and amberlyst-15 : Two efficient heterogeneous catalysts for single-step synthesis of 4(3H)-quinazolinones from anthranilic acid, ortho esters, and amines under solvent free conditions
Das, Biswanath,Banerjee, Joydeep
, p. 960 - 961 (2004)
The single step synthesis of 4(3H)-quinazolinones has been carried out efficiently by coupling of the three components, anthranilic acid, ortho esters, and amines in the presence of silica-supported sodium hydrogen sulfate (NaHSO4·SiO2) or Amberlyst-15 as a heterogeneous catalyst. The reaction occurred within a few minutes under solvent free conditions to afford the products in excellent yields. One of the catalysts, Amberlyst-15 can be recovered and recycled.
New and efficient synthesis of 3-arylquinazolin-4(1H)-ones and biologically important N-fused tetracycles based on N-(2-carboxyphenyl)oxalamide
Mamedov, Vakhid A.,Mamedova, Vera L.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Voronina, Julia K.,Kushatov, Temur A.,Korshin, Dmitry E.,Samigullina, Aida I.,Tanysheva, Ekaterina G.,Kh. Rizvanov, Il'dar,Latypov, Shamil K.
, (2021/09/28)
A novel clean, one-pot syntheses of 3-arylquinazolin-4(3H)-ones and quinoxalino[2,1-b]quinazoline-6,12(5H)-diones via PPA-mediated coupling of N-(2-carboxyphenyl)oxalamides with arylamines and 1,2-benzenediamines have been developed. Under mild reaction conditions with use of Na2S2O4 the benzimidazo[2,1-b]quinazolin-12-ones were achieved in good yield from 3-(2-nitrophenyl)quinazolin-4-ones.
Metal-free C-H methylation and acetylation of heteroarenes with PEG-400
Kudale, Vishal Suresh,Wang, Jeh-Jeng
supporting information, p. 3506 - 3511 (2020/06/25)
The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.
Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones
Bao, Yajie,Yan, Yizhe,Xu, Kun,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
, p. 4736 - 4742 (2015/05/13)
A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.
Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: Applications towards the synthesis of drugs
Kumar, Dinesh,Jadhavar, Pradeep S.,Nautiyal, Manesh,Sharma, Himanshu,Meena, Prahlad K.,Adane, Legesse,Pancholia, Sahaj,Chakraborti, Asit K.
, p. 30819 - 30825 (2015/04/22)
Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 °C for 5 h or under microwave irradiation at 140°C for 20-30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl)vinyl)quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.
A convenient palladium-catalyzed carbonylative synthesis of 4(3H)-quinazolinones from 2-bromoformanilides and organo nitros with Mo(CO) 6 as a multiple promoter
He, Lin,Sharif, Muhammad,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
supporting information, p. 3763 - 3767 (2014/08/05)
A novel and convenient procedure for the synthesis of quinazolinones has been developed. Using 2-bromoformanilides and organo nitros as substrates and Mo(CO)6 as a multiple promoter, the desired products were isolated in moderate to excellent yields in the presence of a palladium catalyst. Here, Mo(CO)6 was not only a CO source, but also a nitro compound reducing reagent and a cyclization promoter. This journal is the Partner Organisations 2014.
Aluminium nitrate-catalyzed one-pot synthesis of 4(3h)-quinazolinones by a three-component coupling of anthranilic acid, amines, and ortho esters
Wang, Min,Song, Zhiguo,Zhang, Tingting
experimental part, p. 385 - 391 (2011/04/15)
The one-pot synthesis of quinazolinone derivatives from the reaction of anthranilic acid, amines, and ortho esters in the presence of aluminium nitrate has been carried out. The reaction occurred in a few minutes at room temperature under solvent-free con
Synthesis of 4-(3H)-quinazolinones by microwave assisted tandem reaction and evaluation of their antibacterial and antifungal activities
Priya, M. Gnana Ruba,Zulykama,Girija,Murugesh,Perumal
experimental part, p. 98 - 102 (2011/04/22)
A one-pot synthesis of quinazolinone derivatives from the reaction of anthranilic acid and primary aromatic amines with Vilsmeier reagent (DMF/POCl3) has been carried out. The reaction occurred in a few minutes under microwave irradiation provi
Silica-supported boron trifluoride (BF3-SiO2): An efficient, environment friendly and recyclable catalyst for the one-pot synthesis of 4(3H)-quinazolinones
Wu, Liqiang,Ma, Weiwei,Yang, Limin,Yan, Fulin
experimental part, p. 6053 - 6058 (2010/12/19)
A simple and efficient synthesis of 4(3H)-quinazolinones has been accomplished by the one-pot condensation of anthranilic acid, triethylorthoformate and primary amines under solvent-free conditions in the presence of BF3-SiO2.
Eco-friendly, solvent-free novel one-pot, three-component synthesis of quinazolinones at ambient temperature catalyzed by silica gel-supported phosphomolybdic acid
Sabitha, Gowravaram,Reddy, N. Mallikarjuna,Prasad, M. Nagendra,Raja,Yadav
experimental part, p. 589 - 593 (2010/09/05)
(Chemical Presented) Silica gel supported Phosphomolybdic acid (PMA.SiO2) catalyzes efficiently the one-pot three-component coupling reaction of anthranilic acid, orthoesters, and amines at room temperature to afford 4(3H)-Quinazolinones in hig
