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GREEN CHEMISTRY · 2024 ·Vol. 26 ·期 20 ·10383-10389 · IF 9.3

Sustainable photocatalytic synthesis of 2-hydroxybenzofuran-3(2H)-ones using lead-free Cs2AgBiBr6 nanocrystals

Haibo Zhu,Ting Zhong,Liu Yang,Yajing Shen,Qiangwen Fan,Zhanggao Le,Zongbo Xie

The photocatalytic activation of oxygen molecules (O2) is an environmentally friendly and sustainable alternative to substituted benzofuran-3(2H)-one synthesis. Herein, lead-free Cs2AgBiBr6 nanocrystals were used to activate O2 efficiently and selectively for the photocatalytic transformation of 4-hydroxycoumarins to functional 2-hydroxy-benzofuran-3(2H)-ones under an air atmosphere. Polyfunctionalized benzofuran-3(2H)-ones with a quaternary carbon center can be selectively obtained in moderate to good yields at room temperature via one-pot synthesis. Perovskite crystal structures have significant influence on photocatalytic activity due to the different charge separation abilities. The reaction mechanism was further investigated to confirm the contribution of reactive oxygen species (ROS).

研究领域: 材料化学 · 有机合成 · 光催化 · 绿色化学 · 纳米材料 · 环境科学 · 可持续化学
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JOURNAL OF SEPARATION SCIENCE · 2019 ·Vol. 42 ·期 15 ·2482-2490 · IF 2.516

Efficient preparative separation of 6-(4-aminophenyl)-5-methyl-4, 5-dihydro-3(2H)-pyridazinone enantiomers on polysaccharide-based stationary phases in polar organic solvent chromatography and supercritical fluid chromatography

Lingping Cheng,Jianfeng Cai,Qing Fu,Yanxiong Ke

6-(4-Aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone is a key synthetic intermediate for cardiotonic agent levosimendan. Very few studies address the use of chiral stationary phases in chromatography for the enantioseparation of this intermediate. This study presents two efficient preparative methods for the isolation of ( R )(−)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone in polar organic solvent chromatography and supercritical fluid chromatography using polysaccharide-based chiral stationary phases and volatile organic mobile phases without additives in isocratic mode. Under optimum conditions, Chiralcel OJ column showed the best performance ( α = 1.71, Rs = 5.47) in polar organic solvent chromatography, while Chiralpak AS column exhibited remarkable separations ( α = 1.81 and Rs = 6.51) in supercritical fluid chromatography with an opposite enantiomer elution order. Considering the sample solubility, runtime and solvent cost, the preparations were carried out on Chiralcel OJ column and Chiralpak AS column (250 × 20 mm i.d.; 10 µm) in polar organic mode and supercritical fluid chromatography mode with methanol and CO 2 /methanol as mobile phases, respectively. By utilizing the advantages of chromatographic techniques and polysaccharide-based chiral stationary phases, this work provides two methods for the fast and economic preparation of ( R )(−)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone, which are suitable for the pharmaceutical industry.

研究领域: 药物化学 · 分析化学
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TETRAHEDRON · 2017 · IF 2.651

“One-pot” sequential preparation of isoquinoline-1,3(2H,4H)-dione derivatives by reacting N-alkyl(aryl)-N-methacryloyl benzamides with benzyl alcohols and sodium benzenesulfinates

Qiujie Tang,Ping Xie,Jin Wang,Jiajun Lin,Chunlai Feng,Charles U. Pittman,Aihua Zhou

Two cascade coupling reactions were developed between N -alkyl(aryl)- N -methacryloyl benzamides and readily available benzyl alcohols or sodium benzenesulfinates . Through a radical cyclization strategy, these one-pot sequential reactions provided two simple and efficient approaches to the synthesis of a variety of isoquinoline-1,3(2H,4H)-dione derivatives in high yields with a broad substrate scope. These compounds are valuable molecules in drug discovery .

研究领域: 有机化学 · 药物化学
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DYES AND PIGMENTS · 2021 · IF 4.889

Design and synthesis of a novel “turn-on” fluorescent probe based on benzofuran-3(2H)-one for detection of hydrazine in water samples and biological systems

Kai Wang,Ya-Xi Ye,Cheng-Yan Jiang,Meng-Ya Guo,Xiang-Yang Zhang,Ai-Qin Jiang,Yu-Shun Yang,Qing-Cai Jiao,Hai-Liang Zhu

Hydrazine is a very important industrial chemical with high toxicity to the human body. In this work, a fluorescent probe HZ , based on the substitution-cyclization-elimination cascade which initiated by hydrazine, was designed and synthesized. HZ had various characteristics such as high selectivity, high sensitivity, fast detection speed, wide application range, and so on. After treating with hydrazine, the fluorescence signal of HZ at 520 nm in aqueous solution was significantly enhanced. Furthermore, HZ had the linear range of 1–10 equivalent for monitoring hydrazine, and the solution showed a colorless to yellow color change. In practical application, the detection limit of HZ for the detection of hydrazine was only 0.75 μM, which could be utilized for trace detection of hydrazine in different water samples. These indicated that HZ had a broad application prospect in the fields of environmental protection and water treatment. This work not only provided a useful instrument for the detection of the ecological environment but also supplied important information for the system optimization of other ecological environment detectors. In addition, HZ could monitor endogenous and exogenous hydrazine in MCF-7 cells successfully, which demonstrated its potential for practical application in complex biological systems.

研究领域: 环境科学 · 分析化学 · 生物学
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SYNTHESIS-STUTTGART · 2022 ·Vol. 54 ·期 11 ·2707-2723 · IF 2.969

Synthesis of Isoquinoline-1,3(2H,4H)-diones by Visible-Light-Mediated Cyclization of Acryloylbenzamides with Alkylboronic Acids, Arylsulfonyl Hydrazides and Oxime Esters

Jiahui Fu,Xingxing Cai,Yihuo Liu,Jinghua Li,Dongping Cheng,Xiaoliang Xu

An efficient visible-light-mediated tandem reaction of acryl­oylbenzamides with alkylboronic acids, arylsulfonyl hydrazides and oxime esters has been developed. The reaction proceeds via radical addition and cyclization to give various isoquinoline-1,3(2H,4H)-diones in satisfactory yields under mild conditions, which provides a good opportunity to discover new meaningful bioactive compounds.

研究领域: 有机化学 · 光化学 · 合成化学
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