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Corresponding Phenols (corresponding + phenol)
Selected AbstractsDevelopment of a photoaffinity label for respiratory syncytial virus inhibitorsJOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, Issue 12 2003Douglas D. Dischino Abstract The syntheses of tritiated and radio-iodinated respiratory syncytial virus inhibitor photoaffinity labels are reported. 3H-1-Isopropyl-3-(1-[2-(3-methyl-3H-diazirin-3-yl)-ethyl]-1H-benzoimidazol-2-yl)methyl)-1,3-dihydrobenzoimid-azol-2-one (1), was prepared in two steps by the initial tritiation of N -isopropenyl-2-benzimidazolone followed by coupling to 2-chloromethyl-1-[2-(3-methyl-3H-diazirin-3-yl)ethyl]-1H-benzoimidazole. The mono and diiodo-radio-iodinated derivatives of 1-(4-hydroxybenzyl)-3-(1-[2-(3-methyl-3H-diazirin-3-yl)-ethyl]-2,3-dihydro-1H-benzo-imidazol-2-ylmethyl)-1,3-dihydro-benzoimidazol-2-one (2, 3), were prepared by the radio-iodination of the corresponding phenol with Na125I and iodogen. Copyright © 2003 John Wiley & Sons, Ltd. [source] Synthesis of a Benzolactone Collection using Click ChemistryEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 1 2007Jan Ritschel Abstract A collection of benzotriazoles consisting of seven compounds was prepared from the propynyl-substituted benzolactone 1 and various azides using click chemistry. The lactone 1 was obtained through a short route by direct esterification of the allylbenzoic acid 9 with the alkynol 7 giving the benzoate 2. The homopropargyl alcohol 7 in turn was obtained by opening the epoxide 6 with triisopropylsilyl acetylide. Ring-closing metathesis of the ester 2 using Grubbs catalyst II followed by removal of the silicon protecting group furnished the lactone 1. Two of the benzotriazoles, 17a and 17b, were also converted into the corresponding phenols to probe the role of the phenolic OH on the biological activity. All nine benzotriazoles showed cytotoxic activity in a L929 mouse fibroblast assay with IC50 values in the low micromolar range. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) [source] Regioselective Synthesis of Phenols and Halophenols from Arylboronic Acids Using Solid Poly(N -vinylpyrrolidone)/ Hydrogen Peroxide and Poly(4-vinylpyridine)/Hydrogen Peroxide ComplexesADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 10 2009K. Surya Prakash Abstract Solid hydrogen peroxide complexes based on poly(N -vinylpyrrolidone) and poly(4-vinylpyridine) were prepared and used as solid hydroxylating reagents. These solid hydrogen peroxide equivalents are found to be much safer, convenient and efficient reagent systems for the ipso -hydroxylation of arylboronic acids to the corresponding phenols in high yields at a faster rate. The versatility of the reagents has been further expanded for the one-pot synthesis of halophenols. Density functional theory calculations were carried out on hydrogen peroxide complexes of N -ethylpyrrolidone and 4-ethylpyridine as models to get a better understanding of structure and behavior of hydrogen peroxide complexes of the polymers poly(N -vinylpyrrolidone) and poly(4-vinylpyridine) compared to aqueous hydrogen peroxide. [source] Primary kinetic hydrogen isotope effects in deprotonations of a nitroalkane by intramolecular phenolate groupsJOURNAL OF PHYSICAL ORGANIC CHEMISTRY, Issue 8 2010Nicholas Backstrom Abstract Rate constants and kinetic isotope effects have been determined for the formation of nitronate anions from the ethers 1-(2-methoxyphenyl)-2-nitropropane, 7(X,=,H, L,=,H and D) and 1-(2-methoxy-5-nitrophenyl)-2-nitropropane, 7(X,=,NO2, L,=,H and D), and from the corresponding phenols, 1-(2-hydroxyphenyl)-2-nitropropane, 3(X,=,H, L,=,H and D), and 1-(2-hydroxy-5-nitrophenyl)-2-nitropropane, 3(X,=,NO2, L,=,H and D), in aqueous basic medium. For the ethers 7, rates of deprotonation by hydroxide are comparable with those found for deprotonations of 2-nitropropane, with kH/kD (25,°C),=,7.7 and 7.8, respectively. In both the cases, the isotope effects are conventionally temperature dependent. For the corresponding phenols 3, conditions have been established under which the deprotonations of the nitroalkane are dominated by intramolecular deprotonation by the kinetically first-formed phenolate anion, with an estimated effective molarity EM,,,250. For 3 (X,=,H, L,=,H or D), kH/kD (25,°C),=,7.8, with E,,,E,=,6.9,kJ,mol,1 and AH/AD,=,0.5. For 3(X,=,NO2, L,=,H or D), rates of intramolecular deprotonation are reduced 30-fold, and an elevated kinetic isotope effect is found (kH/kD (25,°C),=,10.7). Activation parameters (E,,,E,=,17.8,kJ,mol,1 and AH/AD,=,0.008) are compatible with an enhanced tunnelling contribution to reactivity in the H-isotopomer. Copyright © 2009 John Wiley & Sons, Ltd. [source] | ||||||||||