3977-52-4Relevant academic research and scientific papers
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.
Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
, p. 979 - 985 (2019/03/12)
Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
Furan-2-carbaldehydes as C1 building blocks for the synthesis of quinazolin-4(3: H)-ones via ligand-free photocatalytic C-C bond cleavage
Yu, Wenjia,Zhang, Xianwei,Qin, Bingjie,Wang, Qiyang,Ren, Xuhong,He, Xinhua
, p. 2449 - 2454 (2018/06/11)
Furan-2-carbaldehydes, as biomass-derived chemicals, are used as efficient green C1 building blocks to synthesize bioactive quinazolin-4(3H)-ones by ligand-free photocatalytic C-C bond cleavage. Notably, protection of hydroxyl, carboxyl, amide, or secondary amino groups is not required. Mechanistic studies suggest that conjugated N,O-tridentate copper complexes act as novel photoinitiators under visible light.
Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions
Kotipalli, Trimurtulu,Kavala, Veerababurao,Janreddy, Donala,Bandi, Vijayalakshmi,Kuo, Chun-Wei,Yao, Ching-Fa
, p. 1182 - 1193 (2016/03/05)
The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.
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.
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
SnCl2·2H2O-catalyzed one-pot synthesis of 4(3H)-quinazolinones from anthranilic acid, ortho esters, and amines under solvent free conditions
Wang, Min,Song, Zhiguo,Zhang, Tingting
experimental part, p. 468 - 471 (2010/06/19)
(Chemical Equation Presented) A simple, efficient, and green procedure for the one-pot synthesis of 4(3H)-quinazolinones by three components condensation of anthranilic acid, ortho esters, and amines in the presence of SnCl 2·2H2O ha
Strontium chloride-catalyzed one-pot synthesis of 4(3H)-quinazolinones under solvent-free conditions
Wang, Min,Song, Zhi Guo,Zhang, Ting Ting
experimental part, p. 1167 - 1170 (2011/10/12)
Strontium chloride was used as an efficient and recyclable catalyst in one-pot condensation of anthranilic acid, ortho esters and amines leading to the formation of 4(3. H)-quinazolinone derivatives in good yields at room temperature under solvent-free co
Synthesis of 3-Aryl-4(3H)-quinazolinones from anthranilic acid, ortho esters, and anilines using Ce(CH3SO3)3· 2H2O as catalyst
Wang, Min,Song, Zhi-Guo,Zhang, Ting-Ting
experimental part, p. 993 - 996 (2011/10/02)
3-Aryl-4(3H)-quinazolinones were synthesized efficiently by the three component one-pot cyclocondensation of anthranilic acid, ortho esters, and anilines in the presence of Ce(CH3SO3)3·2H 2O at room temperature under solve
