613-69-4Relevant academic research and scientific papers
C70Fullerene Catalyzed Photoinduced Aerobic Oxidation of Benzylamines to Imines and Aldehydes
Kumar, Inder,Kumar, Rakesh,Gupta, Shiv Shankar,Sharma, Upendra
supporting information, p. 6449 - 6457 (2021/05/29)
C70 fullerene catalyzed photoinduced oxidation of benzylic amines at ambient conditions has been explored here. The developed strategy's main feature includes the additive/oxidant-free conversion of benzylic amine to corresponding imine and aldehydes. The reaction manifests broad substrate scope with excellent function group leniency and is applicable up to the gram scale. Further, symmetrical secondary amines can also be synthesized from benzylic amine in a one-pot two-step process. Various experiments and density functional theory studies revealed that the current reaction involves the generation of reactive oxygen species, single electron transfer reaction, and benzyl radical formation as key steps under photocatalytic conditions.
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.
Catalyst-free photodecarbonylation ofortho-amino benzaldehyde
Li, Lamei,Wang, Songping,Wei, Wentao,Yan, Ming,Zhou, Jingwei
supporting information, p. 3421 - 3426 (2020/06/25)
It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.
Method for synthesizing aromatic aldehyde through iron catalyzed oxidation allyl aromatic compound
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Paragraph 0090-0092; 0150, (2019/06/27)
The invention discloses a method for synthesizing aromatic aldehyde through an iron catalyzed oxidation allyl aromatic compound. According to the specific method, under the promotion effect of hydrogen silane, with air or oxygen as the oxidant, the aromatic aldehyde compound is synthesized through the iron catalyzed oxidation allyl aromatic compound, the reaction temperature is 20-150 DEG C, and the time is 0.25-60 h. The method has the advantages that a catalyst source is wide, the price is low and the environment is protected; an oxidant source is wide, the price is low and no waste is generated; the reaction conditions are mild, selectivity is high and the yield is high; a substrate source is wide and stable; a substrate functional group is high in compatibility and a substrate is widein application range; complicated small molecules are compatible and can be well converted into aldehyde. The target product separation yield can reach up to 96% under the optimized reaction conditions.
Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics
Hussein, Waleed M.,Feder, Daniel,Schenk, Gerhard,Guddat, Luke W.,McGeary, Ross P.
, p. 462 - 479 (2018/08/21)
Purple acid phosphatases (PAPs) are metalloenzymes that catalyse the hydrolysis of phosphate esters under acidic conditions. Their active site contains a Fe(III)Fe(II) metal centre in mammals and a Fe(III)Zn(II) or Fe(III)Mn(II) metal centre in plants. In humans, elevated PAP levels in serum strongly correlate with the progression of osteoporosis and metabolic bone malignancies, which make PAP a target suitable for the development of chemotherapeutics to combat bone ailments. Due to difficulties in obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ～30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions are conserved. The crystal structure of red kidney bean PAP in complex with the most potent inhibitor in this series, compound 4f, was solved to 2.40 ? resolution. This inhibitor coordinates directly to the binuclear metal centre in the active site as expected based on its competitive mode of inhibition. Docking simulations predict that this compound binds to human PAP in a similar mode. This study presents the first example of a PAP structure in complex with an inhibitor that is of relevance to the development of anti-osteoporotic chemotherapeutics.
Fungal biofilm inhibition by piperazine-sulphonamide linked Schiff bases: Design, synthesis, and biological evaluation
Patil, Rajendra H.,Kalam Khan, Firoz A.,Jadhav, Kaivalya,Damale, Manoj,Akber Ansari, Siddique,Alkahtani, Hamad M.,Ali Khan, Azmat,Shinde, Shantanu D.,Patil, Rajesh,Sangshetti, Jaiprakash N.
, (2018/03/21)
We report the synthesis of some new piperazine-sulphonamide linked Schiff bases as fungal biofilm inhibitors with antibacterial and antifungal potential. The biofilm inhibition result of Candida albicans proposed that the compounds 6b (IC50 = 32.1 μM) and 6j (IC50 = 31.4 μM) showed higher inhibitory activity than the standard fluconazole (IC50 = 40 μM). Compound 6d (MIC = 26.1 μg/mL) with a chloro group at the para position was found to be the most active antibacterial agent of the series against Bacillus subtilis when compared with the standard ciprofloxacin (MIC = 50 μg/mL). Compound 6j (MIC = 39.6 μg/mL) with an OH? group at the ortho position showed more potent antifungal activity as compared to that of the standard fluconazole (IC50 = 50 μM) against C. albicans. Thus, the synthesized compounds 6a–k were found to be potent biofilm inhibitors as well as active antibacterial and antifungal agents. The molecular docking study of the synthesized compounds against the secreted aspartyl protease (SAP5) enzyme of C. albicans exhibited good binding properties. The in silico ADME properties of the synthesized compounds were also analyzed and showed their potential to be developed as potential oral drug candidates.
Synthesis of 5-arylisoxazole-3-carboxylates derived from salicylaldehyde
Petkevich, S. K.,Dikusar, E. A.,Potkin, V. I.,Mikhei, I. V.
, p. 33 - 41 (2015/03/18)
A procedure has been developed for the synthesis of 5-arylisoxazole-3-carboxylates on the basis of phenols and oximes derived from salicylaldehyde. Selective reduction of 4-(2-ethoxybenzylideneaminophenyl) 5-arylisoxazole-3-carboxylates afforded the corresponding amines.
Solid supported Ru(0) nanoparticles: An efficient ligand-free heterogeneous catalyst for aerobic oxidation of benzylic and allylic alcohol to carbonyl
Das, Pralay,Aggarwal, Nidhi,Guha, Nitul Ranjan
supporting information, p. 2924 - 2928 (2013/06/27)
Polymer immobilized stable, spherical ruthenium nanoparticles were prepared, characterized, and acted as a heterogeneous catalyst for the selective benzylic and allylic alcohol oxidation into the corresponding carbonyls using molecular oxygen. The solid supported Ru(0) (SS-Ru) as a heterogeneous catalyst exhibits good reusability and easy separation from the reaction mixture by filtration.
Solid-supported Pd(0): An efficient heterogeneous catalyst for aerobic oxidation of benzyl alcohols into aldehydes and ketones
Bandna,Aggarwal, Nidhi,Das, Pralay
supporting information; experimental part, p. 4954 - 4956 (2011/10/08)
Solid-supported nano- and microparticles of Pd(0) (SS-Pd) were used as heterogeneous catalysts for aerobic oxidation of benzyl alcohols. Primary and secondary benzyl alcohols gave the corresponding products in good yields. In addition, the catalysts could be reused up to five runs without significant loss of activities.
Electrophilic carbon transfer in gold catalysis: Synthesis of substituted chromones
Renault, Jacques,Qian, Zhao,Uriac, Philippe,Gouault, Nicolas
supporting information; experimental part, p. 2476 - 2479 (2011/05/16)
Using easily accessible aromatic alkoxy-arylalkynones, we have investigated the gold-catalyzed intramolecular addition of ethers to alkynes, to give easy access to various substituted chromones. This reaction involves the transfer of the ether substituent via a carbodemetallation process. We also noticed a competing isomerization of several starting materials for which we propose a second gold catalyzed mechanism.
