1012-59-5Relevant academic research and scientific papers
Microwave-assisted synthesis of quinazolin-4(3H)-ones catalyzed by SbCl
Kang, Huaiyuan,Wang, Weili,Sun, Qinqiang,Yang, Shuya,Jin, Juan,Zhang, Xuewen,Ren, Xiaoliang,Zhang, Jiming,Zhou, Jianhua
, p. 293 - 296 (2018)
Antimony(III) trichloride (SbCl3) is an effective catalyst (1 mol%) for the condensation of anthranilic amide with various aldehydes or ketones to quinazolin-4(3H)-one derivatives in good to excellent yields under microwave irradiation. The process is carried out within several minutes under solvent-free conditions. This general methodology has the advantages of simplicity, mild reaction conditions and high yields of products.
Facile method for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by SiO2–H3PW12O40 in water
Alinezhad, Heshmatollah,Soleymani, Elham,Zare, Mahboobeh
, p. 457 - 466 (2017)
The 12-tungstophosphoric acid supported on silica gel (PW/SiO2) exhibits excellent activity in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation reaction of 2-aminobenzamide with carbonyl compounds in water under reflux conditions. The desired products have been obtained in short reaction times in high yields. Our method has been successfully applied for both aldehydes and ketones (aromatic and aliphatic). Easy recovery and reusable catalyst, easy work-up and avoidance of using harmful organic solvents are the major advantages of our method in comparison to existing methods.
Selective synthesis of functionalized quinazolinone derivatives via biocatalysis
Gong, Bozhen,Lan, Jin,Le, Zhanggao,Li, Hongxia,Meng, Jia,Xie, Zongbo
, (2020)
A novel and efficient biocatalyzed methodology for the construction of functionalized quinazolinone derivatives via tandem / hydrolysis / decarboxylation / cyclization and transesterification reactions has been developed that works with a variety of 2-aminobenzamide and β-dicarbonyl compounds. This method requires mild conditions, and has demonstrated high catalytic activity, excellent yields, excellent chemoselectivity, and a broad substrate scope. Additionally, biocatalyzed decarboxylation does not require high temperatures or light activation, giving it a substantial advantage over alternative techniques. Most importantly, it offers a new example for the exploration of simple, convenient, and environmentally friendly synthetic routes utilizing enzymes in organic chemistry.
One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in the Presence of a Molecular Sieve Supported Lanthanum Catalyst
Magyar, ágnes,Hell, Zoltán
, p. 1153 - 1162 (2016)
Abstract: A series of 2,3-dihydroquinazolin-4(1H)-ones have been synthesized with good to excellent yields by one-pot reaction using isatoic anhydride, aldehydes, and ammonium acetate or amines in acetonitrile in the presence of 4 ? molecular sieve modified with lanthanum(III) as an efficient heterogeneous catalyst. The catalyst could be reused without evident loss of activity. Graphical Abstract: [Figure not available: see fulltext.]
Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives
Yang, Jiangnan,Xie, Zongbo,Chen, Zhongsheng,Jin, Liang,Li, Qian,Le, Zhanggao
, p. 1496 - 1501 (2021/05/03)
A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.
Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: Synthesis of natural products and drugs
Ghosh, Suman Kr,Nagarajan, Rajagopal
, p. 27378 - 27387 (2016/04/04)
A mild and greener protocol was developed to synthesize substituted quinazolinones and dihydroquinazolinones via deep eutectic solvent (DES) mediated cyclization with a series of aliphatic, aromatic, and heteroaromatic aldehydes in good to excellent yields. This greener strategy was further utilised to synthesize various quinazolinone natural products and drugs.
Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones catalyzed by graphene oxide nanosheets in an aqueous medium: "on-water" synthesis accompanied by carbocatalysis and selective C-C bond cleavage
Kausar, Nazia,Roy, Indranil,Chattopadhyay, Dipankar,Das, Asish R.
, p. 22320 - 22330 (2016/03/15)
Graphene oxide (GO) nanosheet catalyzed new and straightforward strategies for the construction of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones starting from anthranilamide (2-aminobenzamide) and an aldehyde/ketone in aqueous medium at room temperature have been realized. This catalyst is also found to be efficient for the expedient construction of quinazolin-4(3H)-ones starting from anthranilamide and a β-ketoester/1,3-diketone following selective C-C bond cleavage of the β-ketoester/1,3-diketone at an elevated temperature under metal and oxidant free conditions.
Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media with β-cyclodextrin-SO3H as a recyclable catalyst
Wu, Jian,Du, Xianli,Ma, Juan,Zhang, Yuping,Shi, Qingcai,Luo, Lijun,Song, Baoan,Yang, Song,Hu, Deyu
supporting information, p. 3210 - 3217 (2014/06/10)
A new β-cyclodextrin-SO3H-assisted, convenient and efficient strategy for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media is described. The catalyst can be readily recovered and reused for the next reaction for at least three runs without any significant impact on the yields of the products. The main advantages of this protocol include short reaction times, practical simplicity, high yields, recyclable catalysts, safety, and cheapness of benign solvents. This journal is the Partner Organisations 2014.
Eco-friendly syntheses of 2,2-disubstituted- and 2-spiroquinazolinones
Mikls, Ferenc,Hum, Veronika,Fül?p, Ferenc
, p. 25 - 37 (2014/12/10)
Environmentally friendly methods were applied to prepare quinazolin-4(1H)-one derivatives in either aqueous or solventless medium from anthranilamide and a number of ketones. With dialkyl-substituted ketones, acetophenone and cycloalkanones, the ring closure proceeded smoothly under either aqueous or solventless conditions. With poorly water-soluble cycloalkanones, the ring closure was carried out under mechanochemical ball-milling conditions, in the presence of molecular iodine as catalyst. The environmentally friendly protocols applied resulted in the corresponding quinazolinones in quantitative yields.
The divergent transformations of aromatic o-aminonitrile with carbonyl compound
Tang, Jianhong,Li, Jiarong,Zhang, Lijun,Ma, Shuling,Shi, Daxin,Zhang, Qi,Yang, Liupan,Wang, Xiuzhen,Liu, Xuan,Liu, Change
experimental part, p. 533 - 542 (2012/08/27)
A modified Friedlaender conversion of the cyclocondensation of aromatic o-aminonitriles with carbonyl compounds was discovered. Systematic studies reveal that both the new transformation and the classic Friedlaender annulation in the presence of ZnCl2 constitute a pair of divergent reaction, and thecontrolled PDF transformation of this divergent reaction was achieved in the present of bases.
