580-18-7Relevant academic research and scientific papers
Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols
Upadhyay, Rahul,Singh, Deepak,Maurya, Sushil K.
supporting information, p. 3925 - 3931 (2021/08/24)
A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.
Convenient synthesis of 3-Hydroxyquinolines via dakin oxidation: A short synthesis of Jineol
Ghorai, Sujit K.,Dasgupta, Mayukh,Dutta, Piyali,Dumeunier, Raphael,Mal, Sanjib,Patre, Rupesh,Kuilya, Tapan Kumar,Pal, Sitaram,Manjunath, Bhanu N.
supporting information, (2020/08/06)
A convenient synthesis of 3-hydroxyquinolines has been described via unprecedented Dakin oxidation of quinoline-3-carboxaldehydes. Subsequently, application of the methodology to a high yielding synthesis of quinoline alkaloid Jineol (1) is reported.
Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid
Song, Zhi-Qiang,Wang, Dong-Hui
supporting information, p. 8470 - 8474 (2020/11/18)
Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.
Design, Synthesis, and Cytotoxic Screening of New Quinoline Derivatives over MCF-7 Breast Cancer Cell Line
Amal, M. Imam,Islam, Zaki
, p. 1099 - 1109 (2020/12/31)
Abstract: VEGFR-2 inhibition represents an attractive strategy for anticancer drug design. A new series of quinoline derivatives were synthesized and structurally confirmed with different spectroscopic techniques. VEGFR-2 inhibition assay showed that 2-(4-bromoquinolin-3-yloxy)-1-(4-chlorophenyl)ethanone (V) demonstrated potent VEGFR-2 inhibitory activities. In addition, the brominated quinoline (V) exhibit antitumor activity over MCF-7 cell line via cell cycle arrest at G1 phase and apoptosis inducing activity as revealed by cell cycle analysis and Annexin V/FITC staining assays. Moreover, brominated quinoline (V) was proved to upregulate expression of proteins that trigger apoptosis such as increased Bax, decreased Bcl-2 as well as increased Bax/Bcl-2 ratio.
Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines
Li, Yushu,Wong, Luet L.
, p. 9551 - 9555 (2019/08/06)
Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.
Room-Temperature Ionic Liquids (RTILs) as Green Media for Metal- and Base-Free ipso -Hydroxylation of Arylboronic Acids
Kim, Seung-Hoi,Kwon, Gyu-Tae,Shin, Eun-Jae
supporting information, p. 1815 - 1819 (2019/09/09)
The oxidative hydroxylation of arylboronic acids to the corresponding phenolic compounds under metal- and base-free aerobic conditions is successfully demonstrated on a greener media. Hydrogen peroxide, as an eco-friendly oxidant, is compatible with green mediates room-temperature ionic liquids (RTIL)s, providing hydroxylation products of arylboronic acids in an efficient manner. The RTIL support is particularly interesting for its reusability.
Recyclable CNT-chitosan nanohybrid film utilized in copper-catalyzed aerobic ipso-hydroxylation of arylboronic acids in aqueous media
Kim, Han-Sem,Joo, Sung-Ryu,Shin, Ueon Sang,Kim, Seung-Hoi
, p. 4597 - 4601 (2018/11/23)
A convenient heterogeneous catalytic system consisting of recyclable and reusable carbon nanotube-chitosan nanohybrid film and copper salt was developed for the aerobic ipso-hydroxylation of arylboronic acids. A variety of arylboronic acids bearing electron-withdrawing or electron-donating groups were smoothly transformed at room temperature in water to afford the corresponding phenols in high yields.
Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis
Wei, Pi-Feng,Qi, Ming-Zhu,Wang, Zhi-Peng,Ding, San-Yuan,Yu, Wei,Liu, Qiang,Wang, Li-Ke,Wang, Huai-Zhen,An, Wan-Kai,Wang, Wei
supporting information, p. 4623 - 4631 (2018/04/10)
The structural uniqueness of covalent organic frameworks (COFs) has brought these new materials great potential for advanced applications. One of the key aspects yet to be developed is how to improve the robustness of covalently linked reticular frameworks. In order to make the best use of π-conjugated structures, we develop herein a ";killing two birds with one stone" strategy and construct a series of ultrastable benzoxazole-based COFs (denoted as LZU-190, LZU-191, and LZU-192) as metal-free photocatalysts. Benefiting from the formation of benzoxazole rings through reversible/irreversible cascade reactions, the synthesized COFs exhibit permanent stability in the presence of strong acid (9 M HCl), strong base (9 M NaOH), and sunlight. Meanwhile, reticulation of the benzoxazole moiety into the π-conjugated COF frameworks decreases the optical band gap and therefore increases the capability for visible-light absorption. As a result, the excellent photoactivity and unprecedented recyclability of LZU-190 (for at least 20 catalytic runs, each with a product yield of 99%) have been illustrated in the visible-light-driven oxidative hydroxylation of arylboronic acids to phenols. This contribution represents the first report on the photocatalytic application of benzoxazole-based structures, which not only sheds new light on the exploration of robust organophotocatalysts from small molecules to extended frameworks but also offers in-depth understanding of the structure-activity relationship toward practical applications of COF materials.
C70 Fullerene-Catalyzed Metal-Free Photocatalytic ipso-Hydroxylation of Aryl Boronic Acids: Synthesis of Phenols
Kumar, Inder,Sharma, Ritika,Kumar, Rakesh,Kumar, Rakesh,Sharma, Upendra
supporting information, p. 2013 - 2019 (2018/04/02)
A metal-free C70 fullerene-catalyzed method has been developed for the ipso-hydroxylation of aryl and heteroaryl boronic acids to corresponding phenols under photocatalytic conditions. The reaction proceeds under oxygen atmosphere and the mechanistic study revealed that C70 plays a critical role in the generation of reactive oxygen species in the presence of blue light. Reactions in the presence of 18O-labelled water and oxygen confirmed the generation of reactive oxygen species from oxygen molecule. Amine used as a reductant could be recovered in the form of imine. The current method is also applicable to the synthesis of aryl ethers in one-pot two-step process. (Figure presented.).
