120-57-0Relevant articles and documents
Production of piperonal, vanillin, and p-anisaldehyde via solventless supported iodobenzene diacetate oxidation of isosafrol, isoeugenol, and anethol under microwave irradiation
Alvarez, Heiddy Marquez,Barbosa, Dayse P.,Fricks, Alini Tinoco,Aranda, Donato A. G.,Valdes, Ricardo H.,Antunes
, p. 941 - 943 (2006)
A novel experimental procedure to obtain carbonyl compounds under microwave irradiation from activated olefins and supported iodobenzene diacetate is described. By varying the reaction conditions it is possible to generate the corresponding aldehydes in reasonable-to-excellent yields and selectivities. The methodology is simple, clean, and reproducible and presents short reaction times. Using isosafrol, isoeugenol, and anethol it was possible to produce piperonal, vanillin and p-anisaldehyde, respectively.
One-Pot Catalytic Approach for the Selective Aerobic Synthesis of Imines from Alcohols and Amines Using Efficient Arene Diruthenium(II) Catalysts under Mild Conditions
Saranya, Sundar,Ramesh, Rengan,Grzegorz Ma?ecki, Jan
, p. 6726 - 6733 (2017)
A green and efficient catalytic approach for the selective synthesis of imines in air at room temperature was achieved with the aid of newly synthesised diruthenium(II) complexes [(η6-p-cymene)2Ru2Cl2(μ-L)] containing substituted 1,2-diacylhydrazine ligands. All the new complexes were fully characterised by analytical and spectroscopic techniques. The solid-state structure of a representative complex was solved by single-crystal X-ray diffraction analysis. The diruthenium(II) complexes also enable the selective aerobic oxidation of alcohols to aldehydes. The catalytic reaction operates in the presence of air as a green and cheap oxidant, and releases water as the only by-product. A plausible mechanism is proposed for the imine formation, which is believed to proceed via an aldehyde intermediate.
Asymmetric glycolate alkylation approach towards total synthesis of 8-O.6′ and 8-O.4′-neolignans
Gangar, Mukesh,Chouhan, Mangilal,Goyal, Sandeep,Harikrishnan,Chandran,Ittuveetil, Avinash,Nair, Vipin A.
, p. 5931 - 5934 (2016)
The glycolate alkylation approach for the total synthesis of 8-O.6′ and 8-O.4′-neolignans has been optimized affording the natural products with high overall yields and excellent stereoselectivity. The developed approach can be further utilized towards the synthesis of many natural and unnatural neolignans. This is the first approach for the synthesis of neolignans using asymmetric glycolate alkylation approach.
A new synthesis of aldehydes by the palladium-catalyzed reaction of 2-pyridinyl esters with hydrosilanes
Nakanishi, Jun,Tatamidani, Hiroto,Fukumoto, Yoshiya,Chatani, Naoto
, p. 869 - 872 (2006)
A new synthesis of aldehydes by the palladium-catalyzed reaction of 2-pyridinyl esters with hydrosilanes is described. The reaction is applicable to the preparation of aliphatic, aromatic, and α,β-unsaturated aldehydes. Various functional groups, such as fluoro, methoxy, aldehyde, acetal, and ester, are tolerated. Georg Thieme Verlag Stuttgart.
A simple biomimetic protocol for the oxidation of alcohols with sodium hypochlorite in the presence of β-cyclodextrin in water
Surendra,Krishnaveni, N. Srilakshmi,Rao, K. Rama
, p. 1230 - 1233 (2004)
A simple and efficient protocol, which is inexpensive, convenient, clean, and facile, for oxidation of alcohols to carbonyl compounds has been developed using sodium hypochlorite in the presence of β-cyclodextrin with water as solvent. A series of alcohols were oxidized at room temperature in excellent yields.
Amino Benzamidoxime (ABAO)-Based Assay to Identify Efficient Aldehyde-Producing Pichia pastoris Clones
Horvat, Melissa,Larch, Tanja-Saskia,Rudroff, Florian,Winkler, Margit
, p. 4673 - 4679 (2020)
The chemoselective synthesis of aldehydes is a challenging task. Nature provides carboxylic acid reductases (CARs) as elegant tools for the direct reduction of carboxylic acids to their respective aldehydes. The discovery of new CARs and strains that efficiently produce these enzymes necessitates a robust high-throughput assay with selectivity for aldehydes. We recently reported a simple assay that allows the substrate independent and chemoselective quantification of aldehydes (irrespective of their chemical structure). The assay utilized amino benzamidoxime (ABAO), which forms UV-active and fluorescent dihydroquinazolines. In this study, we adapted the ABAO-assay for the identification and comparison of Pichia pastoris clones with the ability to produce aldehydes from carboxylic acids. Specifically, CAR and PPTase from Mycobacterium marinum (MmCAR and MmPPTase) were co-expressed using different bidirectional promoters (BDPs). A library of 598 clones was screened for piperonal production with the ABAO assay and the results were validated by HPLC quantification. 1 OD unit of the best Pichia pastoris clone 2.A7, regulating MmCAR and MmPPTase expression by two strong constitutive promoters, fully converted 5 mM of piperonylic acid within 2 h. (Figure presented.).
Structural optimization of caffeoyl salicylate scaffold as NO production inhibitors
Yu, Pan,Xia, Chao-Jie,Li, Dong-Dong,Wang, Zhenzhong,Xiao, Wei,Zhao, Lin-Guo
, p. 1006 - 1014 (2019)
Chlorogenic acid (CGA) has been considered as one of important active components in a number of medicinal herbs. Recently our group demonstrated that caffeoyl salicylate scaffold derived from CGA can be employed for the development of novel anti-inflammatory agents. The most active compound D104 can be a very promising starting point for the further structural optimization. A series of novel caffeoyl salicylate analogs were designed, synthesized, and evaluated by preliminary biological evaluation. The obtained results showed that the two compounds B12 and B13 can not only inhibit production of nitric oxide (NO) in RAW264.7 cells induced by lipopolysaccharides (LPS) effectively, but also have high safety in in vitro cytotoxic test, which could be comparable with D104. Molecular docking study on the peroxisome proliferator-activated receptor γ (PPARγ) protein revealed that compounds B12 and B13 can follow the same binding mode with D104, and the carboxyl group of caffeoyl salicylate scaffold might play a key role in the interaction with protein target, which implied the carboxyl group should be retained in the further optimization.
Design, synthesis, biological evaluation, homology modeling and docking studies of (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene) pyrrolidin-2-one derivatives as potent anticonvulsant agents
Wang, Tiantian,Dong, Shiyang,Chen, Xiaodong,Qian, Kun,Wang, Huayu,Quan, Hexiu,Zhang, Zhongli,Zuo, Yueming,Huang, Liping,Li, Dongxun,Yang, Ming,Yang, Shilin,Jin, Yi,Wang, Zengtao
, p. 1324 - 1329 (2018)
A series of (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)pyrrolidin-2-one derivatives were designed, synthesized, and evaluated for their anticonvulsant activities. In the preliminary screening, compounds 5, 6a–6f and 6h–6i showed promising anticonvulsant activities in MES model, while 6f and 6g represented protection against seizures at doses of 100 mg/kg and 0.5 h in scPTZ model. The most active compound 6d had a high-degree protection against the MES-induced seizures with ED50 value of 4.3 mg/kg and TD50 value of 160.9 mg/kg after intraperitoneal (i.p.) injection in mice, which provided 6d in a high protective index (TD50/ED50) of 37.4 comparable to the reference drugs. Beyond that, 6d has been selected and evaluated in vitro experiment to estimate the activation impact. Apparently, 6d clearly inhibits the Nav1.1 channel. Our preliminary results provide new insights for the development of small-molecule activators targeting specifically Nav1.1 channels to design potential drugs for treating epilepsy. The computational parameters, such as homology modeling, docking study, and ADME prediction, were made to exploit the results.
Simple system for oxidation of alcohols in aqueous solution
Telvekar, Vikas N.,Jadhav, Nikhil C.
, p. 3107 - 3111 (2008)
A simple and mild system for conversion of primary and secondary alcohols to corresponding aldehydes and ketones has been developed using aqueous sodium dichloroiodate at room temperature in water. This novel application of aqueous sodium dichloroiodate gives high yield and offers a number of advantages in terms of safety and ease of use in comparison to other methods that often employ toxic and hazardous solvents and materials. Copyright Taylor & Francis Group, LLC.
Design and Synthesis of 5-Substituted Benzo[d][1,3]dioxole Derivatives as Potent Anticonvulsant Agents
Dong, Shiyang,Wang, Tiantian,Hu, Chundi,Chen, Xiaodong,Jin, Yi,Wang, Zengtao
, (2017)
A series of 5-substituted benzo[d][1,3]dioxole derivatives was designed, synthesized, and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Neurotoxicity was determined by rotarod test. In the preliminary screening, six compounds, 3a, 3c, 3d, and 4d–f, showed promising anticonvulsant activities in the MES model, and compounds 4c and 4d exhibited full protection against seizures at doses of 300 mg/kg in the scPTZ model. Among the synthesized compounds, 3c as the most active compound showed high protection against the MES-induced seizures with an ED50 value of 9.8 mg/kg and a TD50 value of 229.4 mg/kg after intraperitoneal injection into mice, thus providing compound 3c with a high protective index (TD50/ED50) of 23.4 comparable to those of reference antiepileptic drugs.
Heterogeneous Oxidation of Allylic and Benzylic Alcohols Catalyzed by Ru-Al-Mg Hydrotalcites in the Presence of Molecular Oxygen
Kaneda, Kiyotomi,Yamashita, Toyokazu,Matsushita, Tsuyoshi,Ebitani, Kohki
, p. 1750 - 1751 (1998)
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Efficient and green oxidation of alcohols with tert-butyl hydrogenperoxide catalyzed by a recyclable magnetic core-shell nanoparticle-supported oxo-vanadium ephedrine complex
Rostami, Amin,Pourshiani, Omid,Darvishi, Neda,Atashkar, Bahareh
, p. 435 - 439 (2017)
A novel method for the oxidation of alcohols to the corresponding carbonyl compounds has been successfully developed using tert-butyl hydrogenperoxide (TBHP) in the presence of a catalytic amount of recyclable magnetic nanoparticle-supported oxo-vanadium ephedrine complex (VO(ephedrine)2@MNPs) in PEG as a green solvent at 80?°C. The catalyst can be magnetically recycled and successfully reused in six subsequent reaction cycles with only slight decreases of its catalytic activity.
Aerobic oxidation of alcohols enabled by nitrogen-doped copper nanoparticle catalysts
Kobayashi, Shū,Tobita, Fumiya,Yamashita, Yasuhiro,Yasukawa, Tomohiro
, p. 1043 - 1048 (2022/03/02)
Heterogeneous nitrogen-doped carbon-incarcerated copper nanoparticle catalysts have been developed. The catalysts promoted the oxidation of alcohols to the corresponding aldehydes, including aliphatic substrates, in high yield in the presence of an N-oxyl
Nickel(II)-Catalyzed Selective (E)-Olefination of Methyl Heteroarenes Using Benzyl Alcohols via Acceptorless Dehydrogenative Coupling Reaction
Balamurugan, Gunasekaran,Ramesh, Rengan
, (2021/11/30)
An efficient catalytic protocol for the synthesis of selective (E)-olefins by the newly synthesized nickel complexes via greener acceptorless dehydrogenative coupling methodology is presented. Two nickel(II) N, S chelating complexes were structurally characterized with the aid of spectral and single crystal X-ray diffraction methods. Olefination of 2-methylheteroarenes with benzyl alcohols via acceptorless dehydrogenative coupling is achieved by inexpensive nickel(II) catalysts. The present olefination protocol is simple and furnishes the desired 2-alkenylheteroarenes in 35 h and yields in the range of 40–93 %. The dehydrogenative coupling reaction proceeds via the generation of an aldehyde intermediate and produces water and hydrogen as sole by-products. The wide substrate scope of this catalytic reaction covered the synthesis of drug intermediates.
One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence
Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
supporting information, p. 18150 - 18155 (2021/12/09)
Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.