- Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr
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Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.
- Mei, Chong,Hu, Yixin,Lu, Wenjun
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supporting information
p. 2999 - 3005
(2018/05/25)
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- Bis(trialkylsilyl) peroxides as alkylating agents in the copper-catalyzed selective mono-: N -alkylation of primary amides
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The copper-catalyzed selective mono-N-alkylation of primary amides with bis(trialkylsilyl) peroxides as alkylating agents was reported. The results of a mechanistic study suggest that this reaction should proceed via a free radical process that includes the generation of alkyl radicals from bis(trialkylsilyl) peroxides.
- Sakamoto, Ryu,Sakurai, Shunya,Maruoka, Keiji
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supporting information
p. 6484 - 6487
(2017/07/10)
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- Annulation of benzamides with [60]fullerene through palladium(II)-catalyzed C-H bond activation
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Palladium-catalyzed heteroannulation of N-substituted benzamides with [60]fullerene, which proceeds through direct sp2 C-H bond activation to form 7-membered ring pallada-intermediate with C60, led to formation of [60]fulleroisoquinolinones in moderate to good yields (8- 64% based on recovered C60). A plausible reaction pathway is proposed. 2011 American Chemical Society.
- Chuang, Shih-Ching,Rajeshkumar, Venkatachalam,Cheng, Chun-An,Deng, Jie-Cheng,Wang, Guan-Wu
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supporting information; experimental part
p. 1599 - 1604
(2011/06/17)
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- Amidation of esters assisted by Mg(OCH3)2 or CaCl2
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Magnesium methoxide (Mg(OCH3)2) and calcium chloride have been shown to facilitate the direct aminolysis of esters by ammonia to primary amides. Methyl, ethyl, isopropyl, and tert-butyl esters were converted to the corresponding carboxamides in good yields. Reactions have been run on a larger scale and without the safety liability inherent in the use of magnesium nitride (Mg3N2). Ammonium chloride and amine hydrochlorides have been used successfully in the place of ammonia with magnesium methoxide.
- Bundesmann, Mark W.,Coffey, Steven B.,Wright, Stephen W.
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experimental part
p. 3879 - 3882
(2010/08/19)
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- Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl x-substituted benzoates
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Second-order rate constants have been measured for the reactions of 2,4-dinitrophenyl X-substituted benzoates (1a-f) with a series of primary amines in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The Bronsted-type plot for the reactions of 1d with primary amines is biphasic with slopes β1 = 0.36 at the high pKa region and β2 = 0.78 at the low pKa region and the curvature center at pKa° = 9.2, indicating that the reaction proceeds through an addition intermediate with a change in the rate-determining step as the basicity of amines increases. The corresponding Bro nsted-type plot for the reactions with secondary amines is also biphasic with β1 = 0.34, β2 = 0.74, and pKa° = 9.1, indicating that the effect of amine nature on the reaction mechanism and pKa° is insignificant. However, primary amines have been found to be less reactive than isobasic secondary amines. The microscopic rate constants associated with the aminolysis have revealed that the smaller k 1 for the reactions with primary amines is fully responsible for their lower reactivity. The electron-donating substituent in the nonleaving group exhibits a negative deviation from the Hammett plots for the reactions of 1a-f with primary and secondary amines, while the corresponding Yukawa-Tsuno plots are linear. The negative deviation has been ascribed to stabilization of the ground state of the substrate through resonance interaction between the electron-donating substituent and the carbonyl functionality.
- Um, Ik-Hwan,Kim, Kyung-Hee,Park, Hye-Ran,Fujio, Mizue,Tsuno, Yuho
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p. 3937 - 3942
(2007/10/03)
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- 11a-Methano-TXA compounds
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The present invention provides novel 11a-methano-TXA compounds and intermediates and processs for their preparation. Further provided are methods for using these novel TXA analogs as inhibitors of thromboxane synthetase, rendering these analogs useful for a variety of pharmacological purposes. These pharmacological uses include anti-inflammatory, anti-thromobitc, and anti-asthma indications.
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