- Selective Bromination of β-Positions of Porphyrin by Self-Catalytic Behaviour of VOTPP: Facile Synthesis, Electrochemical Redox Properties and Catalytic Application
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Oxidovanadium(IV) complex of β-octabromo-meso-tetraphenylporphyrin, {[VIVO(TPPBr8)], 2} was synthesized by self-catalytic oxidative bromination of meso-tetraphenylporphyrinatooxidovanadium(IV) {[VIVO(TPP), 1} in excellent yield under mild conditions at 25 °C and its structure was confirmed by single crystal X-ray study. UV-Vis and 1H NMR spectra further confirmed that the meso-phenyl rings are not brominated and thus emphasizes on the selectivity as well as synthetic importance of this catalytic method. In the presence of substrates e. g. phenol derivatives, 1 biomimics the vanadium bromoperoxidase (VBPO) enzyme and catalyses the oxidative bromination of substrates in water at 25 °C. Remarkably, 2 also catalyses the oxidative bromination of phenol derivatives under similar reaction conditions with very high turnover frequency (TOF) values (ca. 29 s?1) along with its recyclability. It was found that 2 showed superior catalytic performance as compared to 1 because of its electron deficient nature due to electron withdrawing bromo substituents and robust saddle shaped nonplanar structure (further supported by DFT studies).
- Maurya, Mannar R.,Prakash, Ved,Avecilla, Fernando,Sankar, Muniappan
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p. 1685 - 1694
(2021/05/03)
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- 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
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Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.
- Khosravi, Kaveh,Naserifar, Shirin
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supporting information
p. 6584 - 6592
(2018/10/05)
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- Synthesis method of 2-methoxy-4-hydroxypropiophenone
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The present invention discloses a synthesis method of 2-methoxy-4-hydroxypropiophenone, and belongs to the field of organic synthesis chemistry. According to the synthesis method disclosed by the present invention, the method comprises the following steps: using phenol as a raw martial; firstly adding a CH3I solution and sodium hydroxide into the phenol to generate p-methylphenol; then adding two oxides such as CaO2 and magnesium oxide into the p-methylphenol to generate p-hydroxybenzaldehyde; then adding a bromine solution and HAC into the p-hydroxybenzaldehyde to further generate 2-bromo-p-hydroxybenzaldehyde; then synthesizing 2-nitro-1-(2-bromo-4-hydroxy)propenyl benzene by adding nitroethan dropwise; adding a solution of Fe and HCl into the 2-nitro-1-(2-bromo-4-hydroxy)propenyl benzene to generate 2-bromo-4-hydroxypropiophenone; and finally adding methanol and PCl3 to finally generate the 2-methoxy-4-hydroxypropiophenone disclosed by the present invention. The embodiment demonstrates that the method disclosed by the present invention is not only simple in operation and low in production cost, but also has a relatively mild reaction process, and the recovery rate is significantly improved and reaches up to more than 85%.
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- DUAL SGLT1/SGLT2 INHIBITORS
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The present invention relates to compounds of Formula (I), or a form thereof, wherein A, R1, R2, R3, R4, and R5 are as defined herein, useful as dual SGLT1/SGLT2 inhibitors.
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Paragraph 0377
(2014/09/29)
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- HYDANTOIN DERIVATES AS KV3 INHIBITORS
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The invention provides compounds of formula (I): Said compounds being inhibitors of Kv3 channels and of use in the prophylaxis or treatment of related disorders.
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Page/Page column 45
(2013/02/27)
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- BORON CONTAINING SMALL MOLECULES
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This invention provides, among other things, novel compounds useful for treating bacterial infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.
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Page/Page column 111-112
(2011/04/24)
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- Asymmetric total syntheses of (-)-variabilin and (-)-glycinol
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Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "interrupted" Feist-Benary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products in over 90% ee in both cases. Other key steps include an intramolecular Buchwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.
- Calter, Michael A.,Li, Na
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supporting information; experimental part
p. 3686 - 3689
(2011/09/14)
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- Flavonoid derivatives as organometallic bioprobes
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The synthesis of organoiron derivatives of biologically active flavonoids is described. Lithium enolates of functionalised protected acetophenones and metallated derivatives of substituted aromatic rings have been employed as nucleophiles in combination with tricarbonyl(η5-cyclohexadienyl)iron electrophiles. Products have been converted into flavonoid and chalcone derivatives. Enolates generated from protected flavanones have also been used in nucleophile addition reactions, and a one-pot in situ protection, nucleophile addition, deprotection sequence is reported.
- Anson, Christopher E.,Creaser, Colin S.,Malkov, Andrej V.,Mojovic, Ljubica,Stephenson, G. Richard
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p. 101 - 122
(2007/10/03)
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- Binding of Phenylalkylamine Derivatives at 5-HT1C and 5-HT2 Serotonin Receptors: Evidence for a Lack of Selectivity
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Certain phenyalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors.It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors.The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other.An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = >0.9, n = 25) between 5-HT1C and 5-HT2 affinity.None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.
- Glennon, Richard A.,Raghupathi, Reva,Bartyzel, Piotr,Teitler, Milt,Leonhardt, Sigrun
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p. 734 - 740
(2007/10/02)
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