- Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions
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The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.
- Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang
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p. 319 - 330
(2021/10/29)
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- Direct Deuteration of Acrylic and Methacrylic Acid Derivatives Catalyzed by Platinum on Carbon in Deuterium Oxide
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The platinum on carbon (Pt/C)-catalyzed deuteration of acrylic and methacrylic acid derivatives in deuterium oxide (D2O) efficiently proceeded to give the corresponding acrylic acid-d3 and methacrylic acid-d5 derivatives. The olefinic functionality, as well as the methyl group on the unsaturated functionality of the substrate, were satisfactorily deuterated via the hydrogen (H)-deuterium (D) exchange reaction. The obtained deuterated compounds are useful building blocks and efficiently converted to the corresponding desired products including a polymer without the degradation of the original deuterium contents. (Figure presented.).
- Park, Kwihwan,Matsuda, Takumi,Yamada, Tsuyoshi,Monguchi, Yasunari,Sawama, Yuka,Doi, Naoki,Sasai, Yasushi,Kondo, Shin-Ichi,Sawama, Yoshinari,Sajiki, Hironao
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supporting information
p. 2303 - 2307
(2018/05/07)
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- Synthesis and refining method of N-alkyl acrylamide
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The invention discloses a synthesis and refining method of N-alkyl acrylamide. The synthesis and refining method comprises the following steps: enabling acyl chloride and primary amine to have amination in a solvent A, washing a reaction product, absorbing impurities, decoloring, cooling, and crystallizing to obtain a crude product, recrystallizing the crude product by using a solvent B, decompressing and drying to obtain a target product. By adopting the synthesis and refining method, the conversion rate of acryloyl chloride is 85 percent or more, and the product purity is 98.5 percent or more.
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Paragraph 0037; 0038
(2018/09/08)
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- N-alkyl acrylamide intermediate and preparation method thereof and preparation method of N-alkyl acrylamide
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The invention belongs to the field of acrylamide, and particularly relates to an N-alkyl acrylamide intermediate and a preparation method thereof and a preparation method of N-alkyl acrylamide.The preparation method of N-alkyl acrylamide comprises the following steps that a cracking reaction is conducted on a compound with the structure of a formula (I) in the presence of a cracking catalyst, and N-alkyl acrylamide with the structure of a formula (VII) is obtained, wherein R1 and R2 are independently selected from alkyl, and n is larger than or equal to 0 and smaller than or equal to 30.The yield of N-alkyl acrylamide prepared through the method is high.It is indicated through experimental results that the total yield of N-alkyl acrylamide prepared through the method is larger than 85%.Please see the formulas in the description.
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Paragraph 0153; 0156; 0157; 0158
(2017/01/26)
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- Synthesis of sialic-acid-group-containing lipid derivatives and application of sialic-acid-group-containing lipid derivatives in pharmaceutical preparations
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The invention provides sialic-acid-group-containing lipid derivatives which are widely used for particle preparation modification. The structure is disclosed as Formula (1), wherein R1 represents one of -OH, -HNCOCH3 and -NHCOCH2OH; the HN-R2-S segment is from SH-R2-NH2; SH-R2-NH2 is a compound containing primary amino group and mercapto group; the R3 segment is from compounds containing alpha,beta-unsaturated conjugated carbonyl; and the R4 segment is from R4-H which is a compound containing hydroxy or primary amino group. The sialic-acid-group-containing lipid derivatives provided by the invention can be used for surface modification of multiple particle preparations, and endow the modification preparation with the targeted distribution capacity.
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Paragraph 0131; 0132; 0133
(2017/06/28)
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- METHOD OF PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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PROBLEM TO BE SOLVED: To provide a method of producing N-substituted (meth)acrylamide of high purity under mild conditions. SOLUTION: This invention relates to a method of obtaining N-substituted (meth)acrylamide [3] by the detachment of an amine compound through the liquid-phase thermal decomposition of an aminopropionic acid amide derivative [1] in the presence of a catalyst mainly composed of silica, wherein R1-R5 are represented by H, a C1-32 alkyl group, and a hydroxyalkyl group. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0055; 0061; 0062
(2018/12/12)
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- Process for the preparation of N-substituted acrylamides
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The present invention relates to a process for the preparation of N-substituted acrylamides of the general formula CH2=CH—CONHR, wherein, R is alkyl group having carbon 1 to 22 or acyl group having carbon 1 to 18. The process for the preparation of the N-substituted acrylamides comprises reacting acrylamide with alkyl acyl chloride in the presence of Lewis acid catalyst in an organic solvent at a temperature ranging between room temperature to 50° C. for a period ranging between 1 hour to 24 hours.
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Page column 4-5
(2008/06/13)
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- Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors with antiinflammatory activity
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A novel series of non-carbohydrate imidazole-based selectin inhibitors has been discovered via high-throughput screening using a P-selectin ELISA-based assay system. The initial lead 1 had an IC50 of 17 μM in the P-selectin ELISA; this potency was significantly improved via an extensive SAR exploration. One of the current lead compounds (29) has an IC50 of 300 nM in a P-selectin ELISA; it also has good activity in P- and E-selectin cell adhesion assays and shows efficacy in vivo. These compounds represent a novel series of sLeX mimetics with antiinflammatory activity. Their unique profile supports our interest in their further evaluation as drug candidates for the treatment of inflammation. Herein we describe the syntheses, optimization, and SAR of this series of novel potent selectin antagonists.
- Slee,Romano,Yu,Nguyen,John,Raheja,Axe,Jones,Ripka
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p. 2094 - 2107
(2007/10/03)
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- Process for the manufacture of α,β-unsaturated N-substituted carboxylic acid amides
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Process for the manufacture of α,β-unsaturated N-substituted carboxylic acid amides of the general formula STR1 in which R1 represents H or CH3 R2 represents H or CH3, and Y represents a divalent straight-chain or branched organic radical having 2-30 carbon atoms, and R3 represents H or the radical of an amine of the formula --N(R4)(R5), in which R4 and R5 represent alkyl radicals having 1 to 4 carbon atoms, by reacting β-substituted carboxylic acid amides of the formula STR2 in which Z represents OH or the radical R6 O--, in which R6 is an alkyl radical having 1 to 4 carbon atoms, with amines of the general formula at temperatures in the range of 100° to 200° C., preferably 120° to 175° C., with the elimination of ammonia, and heating the resulting N-substituted β-hydroxycarboxylic or β-alkoxycarboxylic acid amides in the presence of catalysts, water or alcohol, respectively, being split off. The water is split off at temperatures of 100°-250° C. with acidic catalysts such as phosphoric acid, or basic catalysts such as sodium hydroxide, and alcohol is split off at 70°-150° C. with basic catalysts such as sodium or potassium hydroxide. The reaction product is separated by distillation, optionally in vacuo.
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