27398-50-1Relevant academic research and scientific papers
Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents
Clososki, Giuliano C.,Costa-Lotufo, Leticia V.,Dos Santos, Thiago,Furtado, Luciana C.,Murie, Valter E.,Nishimura, Rodolfo H. V.
, p. 2968 - 2975 (2022/01/12)
Microwave-mediated N-arylation of 4-chloroquinazolines in THF/H2O rapidly and efficiently afforded a library of novel 6-halo-2- phenyl-substituted 4-anilinoquinazolines. The methodology was compatible with numerous ortho-, meta-, and para-substituted N-methylanilines as well as substituted anilines and furnished the corresponding 4-anilinoquinazolines in good yields. Preliminary screening of the synthesized compounds against tumor cells (HCT-116 and T98G) showed promising antiproliferative properties.
Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
supporting information, p. 15117 - 15127 (2021/10/25)
A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones
Wang, Rongzhou,Liu, Shiyuan,Li, Longfei,Song, Ao,Yu, Shengsheng,Zhuo, Shuping,Xing, Ling-Bao
, (2021/07/07)
In the present work, we have developed a novel and environmentally friendly method for the synthesis of quinazolinones using fluorescein as a photocatalyst via a condensation reaction of o-aminobenzamides and aldehydes under visible light irradiation. In this protocol, neither toxic oxidants nor transition-metal catalysts were needed, and a series of quinazolinones could be obtained in high efficiencies. In addition, this reaction can be extended to gram levels and has a large potential of wide application in future industrialization.
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.
Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation
Liu, Xuexin,Chen, Jian,Yang, Chunyan,Wu, Zhouping,Li, Zhiyang,Shi, Yuesen,Huang, Tianle,Yang, Zhongzhen,Wu, Yong
supporting information, p. 6831 - 6835 (2021/09/08)
Three-component couplings have been realized for efficiently constructing various nitrogen-containing skeletons via C-H activation, where difluorocyclopropenes have been first identified as coupling partners. Many substrates including sp2 and sp3 C-H substrates were well tolerated, furnishing the corresponding products in good yields. Furthermore, a catalyst-dependent reaction was also developed, enabling divergent construction of two different frameworks. The application value of these reactions was demonstrated in gram-scale experiments with as little as 1 mol % catalyst.
Green synthesis method and application of quinazolinone compound
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Paragraph 0032; 0043-0044; 0047, (2021/04/07)
The invention discloses a green synthesis method and application of a quinazolinone compound. The structure of the quinazolinone compound is shown as a formula I, the preparation method comprises the following steps: by taking an R1-substituted hexafluoroisopropanol 2-aminobenzoate compound and R2-substituted amidine hydrochloride as raw materials, alkali as an additive, and acetonitrile, dioxane, tetrahydrofuran, DMSO (dimethylsulfoxide) or DMF (dimethyl formamide) as a solvent, reacting at normal temperature to generate the quinazolinone compound shown in the formula I. The method provided by the invention has the advantages of no need of heating, no need of using a metal catalyst, mild reaction conditions, no generation of by-products in the reaction, 100% conversion of the raw materials and simple post-treatment process, can be used to obtain the high-purity quinazolinone product, and is a simple green synthesis method; and the quinazolinone compound has high antitumor activity, and can be used for preparing antitumor drugs.
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.
Pd/C Catalyzed Cascade Synthesis of 2-Arylquinazolinones from 2-Iodoacetanilides Employing Ammonia and CO Precursors
Shaifali,Mehara, Pushkar,Kumar, Ashish,Das, Pralay
, p. 2459 - 2464 (2021/03/31)
An efficient and straightforward approach has been demonstrated for 2-aryl quinazolinones synthesis from 2-iodoacetanilides using ammonium carbamate/ammonium carbonate and oxalic acid under heterogeneous Pd/C catalyzed conditions. Herein, we have carried
Ruthenium(II)-catalyzed C?C/C?N coupling of 2-arylquinazolinones with vinylene carbonate: Access to fused quinazolinones
Wang, Zhao-Hui,Wang, He,Wang, Hua,Li, Lei,Zhou, Ming-Dong
supporting information, p. 995 - 999 (2021/03/03)
In this work, ruthenium(II)-catalyzed C?C/C?N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range of substrates with excellent functional-group compatibility. In this transformation, the vinylene carbonate acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and a plausible catalytic cycle was also proposed.
Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature
Chen, Jiewen,Liang, En,Shi, Jie,Wu, Yinrong,Wen, Kangmei,Yao, Xingang,Tang, Xiaodong
, p. 4966 - 4970 (2021/02/06)
Herein, we describe the novel reactivity of hexafluoroisopropyl 2-aminobenzoates. The metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates has been developed at room temperature. These procedures feature
