27398-50-1Relevant academic research and scientific papers
Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from o-Aminobenzonitriles
Hao, Shushu,Yang, Jiazhi,Liu, Peng,Xu, Jing,Yang, Chenchen,Li, Feng
supporting information, p. 2553 - 2558 (2021/04/13)
A linear-organic-polymer-supported iridium complex Cp*Ir@P4VP, which is designed and synthesized by the coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.
Electrochemically induced synthesis of quinazolinonesviacathode hydration ofo-aminobenzonitriles in aqueous solutions
Yang, Li,Hou, Huiqing,Li, Lan,Wang, Jin,Zhou, Sunying,Wu, Mei,Ke, Fang
supporting information, p. 998 - 1003 (2021/02/16)
An efficient and practical electrochemically catalyzed transition metal-free process for the synthesis of substituted quinazolinones from simple and readily availableo-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water play an unprecedented and vital role in the reaction. By electrochemically catalysed hydrolysis ofo-aminobenzonitriles, the synthesis of quinazolinones with benzaldehyde was first proposed. The synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactiveN-(2,5-dichlorophenyl)-6-(2,2,2-trifluoroethoxy) pteridin-4-amine, which enables straightforward, practical and environmentally benign quinazolinone formation.
Preparation method of quinazolinone derivative
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Paragraph 0091-0094, (2021/04/14)
The invention discloses a preparation method of a quinazolinone derivative, wherein the preparation method comprises the following steps: dissolving an anthranilonitrile compound represented by a formula I and an aldehyde represented by a formula II in a
Electro-oxidative cyclization: Access to quinazolinones: Via K2S2O8without transition metal catalyst and base
Hou, Huiqing,Hu, Yongzhi,Ke, Fang,Sun, Weiming,Wu, Xianghua,Yu, Ling,Zhou, Sunying
, p. 31650 - 31655 (2021/11/30)
A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure, leading to the formation of nitrogen heterocycles via direct oxidative cyclization at room temperature in a one-pot procedure under constant current. Owing to the use of continuous-flow electrochemical setups, this green, mild and practical electrosynthesis features high efficiency and excellent functional group tolerance and is easy to scale up.
Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution
Hou, Huiqing,Ma, Xinhua,Lin, Yingying,Lin, Jin,Sun, Weiming,Wang, Lei,Xu, Xiuzhi,Ke, Fang
, p. 17721 - 17726 (2021/05/29)
The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.
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.
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.
