- Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights
-
We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).
- Kurouchi, Hiroaki,Sai, Masahiro
-
supporting information
p. 3585 - 3591
(2021/06/27)
-
- Synthesis method of 4-acryloylmorpholine
-
The invention discloses a synthesis method of 4-acryloylmorpholine. The synthesis method mainly comprises the following two steps: 1) carrying out dehydration condensation on propionic acid and morpholine under the action of DCC to obtain an intermediate 4-propionylmorpholine; and 2) carrying out a Saegusa reaction on the 4-propionylmorpholine and oxygen under the catalysis of palladium acetate under the condition of a strong base to form the target product 4-acryloylmorpholine. The synthesis method of the 4-acryloylmorpholine can be implemented under normal pressure, reaction temperature is mild, byproducts are few, a reaction catalyst can be recycled, and the synthesis method has good industrialization prospects.
- -
-
Paragraph 0021-0026
(2021/06/26)
-
- Method for catalytically synthesizing acrylamide compound by MOFs-derived zirconium-based ternary oxide solid acid
-
The invention provides a catalytic synthesis of acrylamide compounds with zirconium-based ternary oxide solid acid as a catalyst, and the low-temperature activity is good. In the synthesis process, the acid is small, the reaction conditions are mild and controllable, the byproducts are few, the reaction yield is effectively improved, the purity is high, the quality is good, and the method is suitable for large-scale production.
- -
-
Paragraph 0063-0064
(2021/11/14)
-
- Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives
-
Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetermination step.
- Sun, Xin,Bai, Xiao-Yan,Li, An-Zhen,Li, Bi-Jie
-
supporting information
p. 2182 - 2187
(2021/03/01)
-
- Copper-Catalyzed Propargylation of Nitroalkanes
-
Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.
- Kim, Raphael S.,Dinh-Nguyen, Linh V.,Shimkin, Kirk W.,Watson, Donald A.
-
supporting information
p. 8106 - 8110
(2020/11/02)
-
- Process for Productions of Formamides and Acrylamides
-
This invention relates to performance chemicals field, it discloses a novel and green process for simultaneous productions of formamides as well as mono- and multi-functional acrylamides under very mild conditions and with high efficiency. These substances are widely useful as industrial solvents or raw materials, in particular acrylamides are important olefinically-unsaturated polymerizable monomers in photo-curing materials.
- -
-
Paragraph 0028; 0029
(2020/02/27)
-
- Preparation method of acryloylmorpholine
-
The invention provides a preparation method of acryloylmorpholine, which comprises the following steps: 1. adding morpholine, acrylic anhydride, a polymerization inhibitor and a catalyst into a deviceprovided with condensation reflux while stirring, and stirring for 2 hours to obtain a mixture A; and 2, filtering the mixture A obtained in the step 1 to obtain a filtrate, and distilling the filtrate to collect a fraction with a temperature range of 65-85 DEG C under 8-12 kPa to obtain the acryloylmorpholine. The yield of the acryloylmorpholine prepared by the method is extremely high and is greater than 90%; and the purity of the product measured by gas chromatography is higher and is greater than 98.0%, so that the technical problems of lower yields and more byproducts in the prior art are solved. Besides, the preparation method is simple and convenient in process and mild in preparation temperature, hardly generates three wastes, is an efficient and environment-friendly synthesis method, and is suitable for large-scale popularization and application.
- -
-
Paragraph 0085-0135
(2020/01/04)
-
- Synthesis method for preparing acryloyl morpholine from acrylamide as raw material
-
The invention relates to a synthesis method for preparing acryloyl morpholine from acrylamide as a raw material and belongs to the field of chemical product synthesis methods. The synthesis method ofthe acryloyl morpholine (ACMO) comprises the following steps: 1) under a condition of 0-5 DEG C, performing a Diels-Alder reaction on acrylamide and furan so as to obtain an acrylamide addition intermediate; 2) performing refluxing on the addition intermediate, morpholine and a catalyst at 100-160 DEG C for 12-24 hours, and performing an amino exchange reaction so as to obtain a propionyl morpholine derivative intermediate; and 3) performing thermal cracking on a propionyl morpholine derivative with a lewis acid catalyst at 130-170 DEG C at 1-3kPa, performing rectification so as to obtain acryloyl morpholine, performing freeze recycling on furan, and circulating the furan for the process. By adopting the acryloyl morpholine synthesis method provided by the invention, the contents of toxicand harmful gases and VOCs (volatile organic compounds) in a production process can be effectively reduced, the reaction process is simple, products and recycled raw materials are easy to separate, the reaction condition is easy to control, the security is high, the reaction yield is high, the byproduct amount is small, the aftertreatment is simple, the product purity is high, and industrial production is easy.
- -
-
Paragraph 0039; 0042; 0043; 0046
(2019/12/09)
-
- Preparation method of N-acryloyl morpholine
-
The invention discloses a preparation method of N-acryloyl morpholine, and particularly relates to a method for preparing N-acryloyl morpholine by a condensation method; acrylic acid and morpholine are used as raw materials, and a dehydrating agent is used for dehydration. The preparation conditions are mild, and the purification process is simple; the product is easy to separate and not easy to polymerize; the preparation method has the advantages of high yield, high product purity and the like in product synthesis.
- -
-
Paragraph 0032-0037
(2019/12/02)
-
- N, N - disubstituted α, β - unsaturated carboxylic acid amide of (by machine translation)
-
[Problem] to compounds derived from compounds containing chlorine atoms contained in the byproducts of the no possibility, stable compound to N, N - disubstituted α, β - unsaturated carboxylic acid amide manufacturing method. [Solution] N, N - di-substituted carboxylic acid amide phenols with formaldehyde, in the presence of a catalyst containing no chlorine atoms, in a nonaqueous liquid phase reaction, N, N - disubstituted α, β - unsaturated carboxylic acid amide having a process, wherein the formaldehyde, paraformaldehyde, trioxane is one selected from formaldehyde and anhydrous 1, 3, 5 - 1, and the catalyst, an acidic catalyst or a basic catalyst N, α N - disubstituted, with production of β - unsaturated carboxylic acid amide. [Drawing] no (by machine translation)
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-
Paragraph 0062; 0063
(2019/06/07)
-
- COMPOSITONS AND METHODS FOR MODULATING UBA5
-
Disclosed herein, inter alia, are compositions and methods useful for inhibiting ubiquitin-like modifier activating enzyme 5.
- -
-
Paragraph 0633; 0634; 0636; 0658
(2018/08/26)
-
- COMPOSITIONS AND METHODS FOR INHIBITING RETICULON 4
-
Disclosed herein, inter alia, are compositions and methods useful for inhibiting reticulon 4(RTN4).
- -
-
Paragraph 0645; 0647; 0671
(2018/08/26)
-
- N, N - disubstituted α, β - unsaturated carboxylic acid amide of (by machine translation)
-
The present invention is [a], the reaction time is short, suitable for mass-production by gas phase reaction N, N - disubstituted α, β - unsaturated carboxylic acid amide manufacturing method. [Solution] N, N - disubstituted α, β - unsaturated carboxylic acid amide is produced, N, N - disubstituted aldehyde carboxylic amide, in the presence of a catalyst, vapor phase reaction, N, N - disubstituted α, β - unsaturated carboxylic acid amide with. [Drawing] no (by machine translation)
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-
Paragraph 0057; 0058; 0059; 0065
(2019/03/07)
-
- COMPOSITIONS AND METHODS FOR MODULATING PPP2R1A
-
Disclosed herein, inter alia, are compositions and methods useful for modulating PPP2R1 A and for the treatment of cancer.
- -
-
Paragraph 0599; 0600; 0607; 0635
(2018/08/26)
-
- Preparation method of single-functionality or multi-functionality acrylamide type compounds
-
The present invention relates to the field of new material fine chemicals, particularly to a new mild, efficient and economical preparation process technology of a class of single-functionality or multi-functionality acrylamide type compounds, wherein the materials are important alkene-containing unsaturated compounds, and are increasingly used in radiation polymerization curing materials or medical application materials and other fields.
- -
-
Paragraph 0015
(2018/07/06)
-
- Preparation method of acryloyl morpholine
-
The invention provides a preparation method of acryloyl morpholine, and particularly relates to a method for preparing the acryloyl morpholine by a pyrolysis method. Dioctadecylamine is adopted as a material to react with acrylic ester; a preparation condition is mild, and a purification process is simple. The product is easy to purify, and polymerism cannot easily take place. In the process of product purification, pyrolysis is effectively prevented from producing volatile amine to react with the product again to produce intermediate impurities. The efficiency of pyrolysis and the yield of the product are increased; the mine produced by pyrolysis cannot easily volatilize, and can be easily recycled, so cost is reduced.
- -
-
Paragraph 0016
(2018/05/16)
-
- Synthesis of Diverse N-Acryloyl Azetidines and Evaluation of Their Enhanced Thiol Reactivities
-
Acyl azetidines exhibit nonplanar hybridization, leading to lower amide-like character of the corresponding (O)C-N bonds. This impacts N-acryloyl azetidines by producing enhanced electrophilicy at appended Michael acceptors. Herein, reactivity data are reported in the presence of glutathione (GSH) in phosphate buffer (pH 7.4) at 37 °C. Wide reactivity ranges are observed by varying substitution at the Michael acceptor or by modulating the electron-withdrawing character of substituents at the C3 position of the azetidine.
- Palkowitz, Maximilian D.,Tan, Bo,Hu, Haitao,Roth, Kenneth,Bauer, Renato A.
-
supporting information
p. 2270 - 2273
(2017/05/12)
-
- Chemoproteomics-enabled covalent ligand screen reveals a cysteine hotspot in reticulon 4 that impairs ER morphology and cancer pathogenicity
-
Chemical genetics has arisen as a powerful approach for identifying novel anti-cancer agents. However, a major bottleneck of this approach is identifying the targets of lead compounds that arise from screens. Here, we coupled the synthesis and screening of fragment-based cysteine-reactive covalent ligands with activity-based protein profiling (ABPP) chemoproteomic approaches to identify compounds that impair colorectal cancer pathogenicity and map the druggable hotspots targeted by these hits. Through this coupled approach, we discovered a cysteine-reactive acrylamide DKM 3-30 that significantly impaired colorectal cancer cell pathogenicity through targeting C1101 on reticulon 4 (RTN4). While little is known about the role of RTN4 in colorectal cancer, this protein has been established as a critical mediator of endoplasmic reticulum tubular network formation. We show here that covalent modification of C1101 on RTN4 by DKM 3-30 or genetic knockdown of RTN4 impairs endoplasmic reticulum and nuclear envelope morphology as well as colorectal cancer pathogenicity. We thus put forth RTN4 as a potential novel colorectal cancer therapeutic target and reveal a unique druggable hotspot within RTN4 that can be targeted by covalent ligands to impair colorectal cancer pathogenicity. Our results underscore the utility of coupling the screening of fragment-based covalent ligands with isoTOP-ABPP platforms for mining the proteome for novel druggable nodes that can be targeted for cancer therapy.
- Bateman,Nguyen,Roberts,Miyamoto,Ku,Huffman,Petri,Heslin,Contreras,Skibola,Olzmann,Nomura
-
supporting information
p. 7234 - 7237
(2017/07/11)
-
- MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE
-
PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
- -
-
Paragraph 0055; 0057; 0059
(2018/07/03)
-
- Preparation method of acrylamide-based compounds
-
The present invention relates to the field of fine chemical materials, particularly to a new mild, efficient and economical preparation process technology of a class of acrylamide-type compounds, wherein a beta-amine substituted propionamide precursor is subjected to an in-situ amine elimination reaction under the action of a suitable electrophilic reagent so as to prepare the target product.
- -
-
Paragraph 0013; 0014; 0015; 0025
(2018/01/11)
-
- Preparation method for oxo-propenylmorpholine
-
The invention relates to a preparation method for oxo-propenylmorpholine, which includes the steps of: performing an aminolysis reaction with polylactic acid and morpholine as raw materials; and then performing an elimination reaction under the effect of a catalyst to produce the oxo-propenylmorpholine, wherein in the aminolysis reaction, reaction temperature is 50-180 DEG C, reaction time is 1-24 h and reaction pressure is 1-5 atm; the molecular weight of the polylactic acid is 500-100000; and the molar ratio of the polylactic acid to morpholine is 1:1-2. In the method, the polylactic acid and morpholine are used as raw materials, so that the method is beneficial to recovery of the polylactic acid and reduces material cost. The method is high in yield and the product is easy to purify. The method is less in reaction steps and simple in operation and is free of generation of an acidic gas, HCl, during the reactions, so that corrosion on reaction equipment is avoided.
- -
-
Paragraph 0023; 0024; 0025; 0027; 0029; 0032
(2017/08/31)
-
- Discovery and SAR of N-(1-((substituted piperidin-4-yl)methyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide derivatives: 5-Hydroxytryptamine receptor 4 agonist as a potent prokinetic agent
-
A series of novel benzamide derivatives, altering the 4-fluorophenylalkyl moiety in cisapride, were synthesized as 5-HT4 receptor agonists, and SAR of these analogs was examined on in vitro and in vivo prokinetic activities. These compounds were synthesized for high 5-HT4 receptor binding affinities and low hERG affinities. Several types of analogs were obtained and screened for 5-HT4 binding, hERG blocking, agonism, and gastric emptying assessment. Among the analogues, compound 23g showed promising results compared with the other analogs with respect to gastric emptying rates in rats. Therefore, we suggest that it may be a clinical candidate for the development of a potent prokinetic agent to treat GI disorders.
- Park, Jung Sang,Im, Weonbin,Choi, Sunghak,Park, Sook Jin,Jung, Jun Min,Baek, Ki Seon,Son, Han Pyo,Sharma, Satyasheel,Kim, In Su,Jung, Young Hoon
-
-
- An acid anhydride-based method for synthesizing acryloyl morpholine (by machine translation)
-
The invention discloses a method for synthesizing acryloyl morpholine based on anhydride. The acryloyl morpholine monomer is generated by performing a reaction of the acrylate trichloroacetic anhydride and the morpholine, and the acrylate trichloroacetic anhydride is obtained by performing a reaction of the acrylic acid and the trichloroacetic acid. The method for synthesizing acryloyl morpholine provided by the invention is simple in process route, easy for reaction control, mild in reaction condition, cheap in raw material, stable in product structure and low in cost; and besides, the method also increases the purity and yield of the product and has an industrial application prospect.
- -
-
Paragraph 0032; 0035; 0036; 0037; 0038; 0041; 0042; 0043
(2019/02/04)
-
- Based on 2- halogen propionyl chloride method of synthesizing acryloyl morpholine (by machine translation)
-
The invention discloses a based on 2- halogen propionyl chloride method of synthesizing acryloyl morpholine, this invention offers a based on 2- halogen propionyl chloride and morpholine generating [...] reaction to form intermediate product 2- halogen propionyl morphline, and sodium in ethanol with a defoaming reaction containing double bond monomer acryloyl morpholine. The invention synthetic method of acryloyl morpholine, the raw materials used are cheap, the structure is stable, synthetic intermediates containing no chirpy group, side reaction is not easy to occur, the yield and the purity of the final product are relatively high. The present invention provides synthetic method process is simple, with the prospects for industrial large-scale production. (by machine translation)
- -
-
Paragraph 0040; 0041; 0042
(2017/03/14)
-
- A acryloyoxyethylbenzy method for the synthesis of amine reactive diluent
-
The invention relates to a synthesis method of an acrylamide type reactive diluent and belongs to the field of organic synthesis. The synthesis method is performed according to the following steps: adding an amide type compound, a formaldehyde solution (or introducing formaldehyde gas) and a catalyst, maintaining the temperature at 80-90 DEG C under stirring conditions and reacting for 15-20h so as to obtain a crude product of the acrylamide type reactive diluent. After the end of reaction, an organic solvent is added for azeotropic dehydration, the catalyst is removed by filtering, a proper amount of polymerization inhibitor is finally added and reduced pressure distillation is performed so as to obtain a product of the acrylamide type reactive diluent. The synthesis method disclosed by the invention can overcome numerous shortcomings of the prior art and realize high yield and simple steps, wherein the yield is about 80% and the purity is more than 98%.
- -
-
Paragraph 0022-0023; 0046-0047; 0048-0049
(2017/02/28)
-
- Method for preparing acryloyl morpholine
-
The invention provides a method for preparing acryloyl morpholine according to a single-container method, and aims to overcome the detects of low yield, high reaction complexity, cumbersome operation and the like. The method provided by the invention has the advantages that the reaction steps are less, and thus the operation is simple; the side reactions are less, and thus the yield is high and the purification is easy; the requirement on reaction equipment of reaction processes is low; corrosion of the reaction equipment is avoided; the environment is protected as generation of the acidic gas hydrogen chloride is avoided; the cost is low; the suitability for industrialized production is high; the superiority to the prior art is considerable.
- -
-
Paragraph 0024
(2016/10/10)
-
- Visible-Light-Driven Intermolecular [2+2] Cycloadditions between Coumarin-3-Carboxylates and Acrylamide Analogs
-
This paper reports a room temperature visible-light-driven protocol for the intermolecular [2+2] cycloadditions between coumarin-3-carboxylates and acrylamides analogs by an energy-transfer process. Using an iridium complex FIrPic as a photosensitizer and a 3W blue LED as a light source, an array of cyclobutabenzocypyranones were prepared in moderate to excellent yields.
- Liu, Qiang,Zhu, Fu-Ping,Jin, Xiao-Ling,Wang, Xiao-Ju,Chen, Han,Wu, Li-Zhu
-
supporting information
p. 10326 - 10329
(2015/07/07)
-
- (Meth) acrylamide N-substituted (by machine translation)
-
PROBLEM TO BE SOLVED: a (meth) acrylic acid and a starting material, high yield, high-purity (meth) and N-substituted carboxylic acid amide derivative norbonene alkylacrylamide industrial production method. SOLUTION: and (meth) acrylic acid aminopentadienoic cyclometallized Diels-Alder reaction product of, norbonene carboxylic acid derivative, and silica as a main catalyst in the presence of an inorganic material, and amide-amine compound, norbonene carboxylic acid amide derivative. Furthermore, the vapor phase of the norbonene vinylcarboxamide deriv. aminopentadienoic cyclometallized by thermal decomposition reaction by desorbing, (meth) acrylamide purpose compd. N-substituted. Selected drawing: no (by machine translation)
- -
-
Paragraph 0054; 0055; 0056; 0057
(2018/12/12)
-
- METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
-
PROBLEM TO BE SOLVED: To provide an industrial method for efficiently producing a high-purity N-substituted (meth)acrylamide in a short time even under mild reaction conditions, which uses (meth)acrylic acid as a starting material and generates only water as a byproduct. SOLUTION: There is provided a method for producing an N-substituted (meth)acrylamide to obtain an objective compound, N-substituted (meth)acrylamide by the step of: reacting a (meth)acrylic and an amine compound to synthesize an aminopropionic acid derivative; then adding an inorganic material composed mainly of silica as a catalyst and performing amidation with the same amine compound to obtain an aminopropionic acid derivative; and subsequently eliminating an amine by the thermal decomposition reaction. COPYRIGHT: (C)2015,JPOandINPIT
- -
-
Paragraph 0053; 0056-0059
(2018/11/22)
-
- METHOD OF PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
-
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
- -
-
Paragraph 0053; 0057; 0058; 0059-0060
(2018/12/12)
-
- METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
-
PROBLEM TO BE SOLVED: To provide an industrial method for producing a high-purity alkoxy propionic acid amide derivative and N-substituted (meth)acrylamide in a high yield, which uses a (meth)acrylic acid as a starting material. SOLUTION: There is provided a method for producing an objective compound, N-substituted (meth)acrylamide by the step of: amidating an alkoxy propionic acid derivative, which is synthesized from a (meth)acrylic acid and alcohol and represented by the formula [1], with an amine compound; R3-NH-R4(R3 and R4 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms or may form a saturated 5- to 7-membered ring with a nitrogen atom supporting them) in the presence of an inorganic material composed mainly of silica as a catalyst to obtain an alkoxy propionic acid amide derivative; and eliminating alcohol by the liquid phase thermal decomposition reaction of the alkoxy propionic acid amide derivative. (R1 represents H or a methyl group; and R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms or an alkenyl group.) COPYRIGHT: (C)2015,JPOandINPIT
- -
-
Paragraph 0057; 0060
(2017/01/05)
-
- Ink composition for inkjet printing, ink set, and image forming method
-
The invention provides an ink composition for inkjet printing, the ink composition containing water, a coloring material, a polymerizable compound, a polymerization initiator represented by the following Formula (X), and polymer particles having a glass transition temperature of 90°C or higher, a mass ratio of the polymer particles to the polymerization initiator represented by Formula (X) being in a range of from 1:10 to 10:1 1 [in Formula (X), each of RX1, RX2, RX3, and RX4 independently represents a hydrogen atom or a substituent; and n represents an integer from 1 to 4].
- -
-
-
- Stereoselective synthesis of natural (2E,4E)-dienamides and their synthetic analogs
-
A procedure has been developed for stereoselective synthesis of a number of naturally occurring (2E,4E)-dienamides and their analogs via palladium-catalyzed reaction of (1E)-1-iodoalk-1-enes with acrylamides. Pleiades Publishing, Ltd., 2012.
- Shakhmaev,Ishbaeva,Zorin
-
p. 908 - 913
(2012/11/06)
-
- Synthesis of 3-pyrroline via domino Heck-aza-Michael reaction
-
This Letter describes the Pd(0)-catalyzed domino Heck-aza-Michael reaction between (Z)-N-(3-iodoallyl)-tosylamide and acrylic ester. The reaction provides a facile access to an important class of substituted 3-pyrroline.
- Wu, Pan,Liu, Hui,Tong, Xiaofeng
-
supporting information; experimental part
p. 4673 - 4675
(2012/09/05)
-
- Micelles for delivery of nitric oxide
-
Embodiments include a vehicle for delivery of nitric oxide comprising: a collection of micelles having an internal micelle core that comprises a polymer with N-diazeniumdiolate comprising NO complexed with secondary amines of the polymer. Embodiments include a method of making a nitric oxide vehicle comprising dissolving a polymer that comprises secondary amines in an aqueous solution and combining the polymer with nitric oxide in the solution to form a N-diazeniumdiolate comprising the nitric oxide complexed with the secondary amines, with the formation of the N-diazeniumdiolate causing the polymer to be at least partially insoluble in the solution and to form a collection of micelles that have an internal core that comprises N-diazeniumdiolate.
- -
-
-
- Preparation of acrylic acid derivatives from alpha-or beta-hydroxy carboxylic acids
-
The invention is directed to a process for the preparation of α,β-unsaturated acids, esters and amides from α- or β-hydroxycarboxylic acids or esters or precursors in high yields and high selectivity. The α,β-unsaturated acids or esters are optionally prepared in the presence of specific dehydration and/or esterification catalysts. The α,β-unsaturated amides or substituted amides are prepared optionally in the presence of a dehydration and/or amidation catalyst. The source of α- or β-hydroxycarboxylic acids or precusor is preferably from a renewable resource. The precursor is defined herein.
- -
-
Page/Page column 10
(2008/06/13)
-
- Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix[4]arenes
-
Upper rim substituted tetraiodo calix[4]arenes are coupled to a variety of acrylamides using the palladium catalysed Heck reaction. Tetra-acrylamido upper rim substituted calix[4]arenes are obtained in good yields with exceptionally high stereoselectivity, to produce the & all-trans isomers. Tetra-acrylamido calix[4]arenes derived from secondary acrylamides are shown to dimerise via eight hydrogen bonds to form dimeric capsules, which are able to include small organic molecules. The Royal Society of Chemistry 2005.
- Kuhnert, Nikolai,Le-Gresley, Adam
-
p. 2175 - 2182
(2007/10/03)
-
- Carbamoylimidazolium and thiocarbamoylimidazolium salts: Novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides
-
Carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents. These salts are readily prepared by the sequential treatment of secondary amines with N,N′-carbonyldiimidazole (CDI) and iodomethane. The carbamoylimidazolium salts are more efficient carbamoyl transfer reagents than the intermediate carbamoylimidazoles, as a result of the 'imidazolium' effect. Kinetic studies on the base promoted hydrolysis of both carbamoylimidazoles and carbamoylimidazolium salts reveal over a hundred-fold rate acceleration. The salts react with amines, thiols, phenols/alcohols, and carboxylic acids in high yields, without the need for subsequent chromatographic purification of the products, producing ureas, thiocarbamates, carbamates, and amides, respectively. Analogous thiocarbamoylimidazolium salts were also synthesized from secondary amines and N,N′-thiocarbonyldiimidazole (TCDI), followed by methylation with iodomethane.
- Grzyb, Justyna A.,Shen, Ming,Yoshina-Ishii, Chiaki,Chi,Brown, R. Stanley,Batey, Robert A.
-
p. 7153 - 7175
(2007/10/03)
-
- Solvent-dependent competitive rearrangements of cyclic tertiary propargylamine N-oxides
-
In protic media, cyclic propargylamine N-oxides 1 undergo solvent-dependent competitive rearrangements leading to enamino aldehydes 5, acrylamides 3, and secondary amines 4. The ratios of the products are evaluated and the possible mechanism of the compet
- Szabo, Anna,Galstnibos-Farago, Agnes,Mucsi, Zoltan,Timari, Geza,Vasvari-Debreczy, Lelle,Hermecz, Istvan
-
p. 687 - 694
(2007/10/03)
-
- Carbamoylimidazolium salts as diversification reagents: An application to the synthesis of tertiary amides from carboxylic acids
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An efficient method for the preparation of tertiary amides from carbamoylimidazolium salts and carboxylic acids is described. The transformation occurs at room temperature and under relatively mild conditions. The carbamoylimidazolium salts are obtained from the reaction of secondary amines with N,N′-carbonyldiimidazole, followed by methylation with methyl iodide. The utility of this reaction was demonstrated in the formation of Weinreb amides and in a short synthesis of fused bicyclic amides. The introduction of this reaction now permits carbamoylimidazolium salts to be utilized in the formation of tertiary amides, ureas, carbamates and thiocarbamates under a single set of conditions.
- Grzyb, Justyna A.,Batey, Robert A.
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p. 7485 - 7488
(2007/10/03)
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- Organic articles
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The invention relates to novel composite materials comprising (a) an inorganic or organic bulk material having covalently bound to its surface initiator moieties for radical polymerization; and (b) a hydrophilic surface coating obtainable by applying one or more different ethylenically unsaturated hydrophilic macromonomers of formula (1) as outlined in the claims to the bulk material surface provided with the initiator radicals and polymerizing said macromonomers. The composite materials of the invention have desirable characteristics regarding adherence to the substrate, durability, hydrophilicity, wettability, biocompatibility and permeability and are thus useful for the manufacture of biomedical articles such as ophthalmic devices.
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- Pyridine derivatives and pharmaceutical compositions containing them
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The invention relates to novel pyridyl derivatives, their use as medicaments, pharmaceutical formulations containing them and methods for their preparation.
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- Deracemization process of α-aminoesters via pyridoxal. II.- Study of copolymerization of polymerizable forms of pyridoxal. Reactivity of corresponding polymers
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We studied the copolymerization of pyridoxal (PL) polymerizable forms, in the presence of two different comonomers (a diluting and crosslinking agent) and the catalytic activity of the corresponding polymers on the α-aminoester racemization.We discuss the choice of these comonomers in the polymerization and also their concentration.Thus, using 4-acryloylmorpholine as a diluting agent, we obtained a sufficiently hydrophilic polymer in an aqueous medium, and the partion coefficient of the substrate was more favorable.In addition, polymer IV, in which the arm allowing immobilization of PL is most distant from the catalytic site, had the highest activity.Keywords: racemization / α-aminoester / pyridoxal analogues / covalent immobilization / polyacrylamide support / radical polymerization
- Honnoraty, Anne-Marie,Mion, Louis,Rousset, Alain,Taillades, Jacques,Commeyras, Auguste
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p. 721 - 728
(2007/10/02)
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- La pronase immobilisee sur poly(N-acryloylpiperidin-4-one): un catalyseur d'hydrolyse L-enantiospecifique des α-aminonitriles
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Pronase immobilized on poly(N-acryloylpiperidin-4-one) : a L-enantiospecific hydrolysis of α-aminonitriles with immobilized amidase. α-Aminonitriles are not substrates for pronase (an amidase) in the homogeneous phase but become substrates for pronase when it is immobilized on polymer matrix with ketonic sites (piperidin-4-one).In this paper we show that under low basic aqueous conditions (pH 10-11), the hydration of α-aminonitriles can be efficiently catalyzed by poly(N-acryloylpiperidin-4-one) crosslinked with 1,4-bis acryloylpiperazine (A(80:20)) in the presence of phosphate or borate buffers.These conditions comply with the hydrolysis of α-aminoamides by pronase immobilized on poly(N-acryloylpiperidin-4-one)crosslinked with 1,4-bis(acryloyl)piperazine (A(80:20/p).Thus, in a buffered borate solution at pH 10.5, α(DL)-aminonitrile is enantiospecifically hydrolyzed into α(D)-aminoamide and α(L)-amino acid. Key words: α-aminonitriles / α amino acids / L-enantiospecific hydrolysis / polymer-supported catalysis / nitrilasic activity
- Taillades, Jacques,Garrel, Laurence,Guillen, Franck,Collet, Helene,Commeyras, Auguste
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p. 119 - 127
(2007/10/02)
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- Hydratation enantioselective d'α-aminonitriles en presence de catalyseurs cetoniques chiraux supportes
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Enantioselective hydration of α-aminonitriles with chiral ketonic immobilized catalyst.In a previous publication, we showed that the hydration of α-aminonitriles under basic aqueous conditions was efficiently catalyzed by a poly(N-acryloylpiperidin-4-one) crosslinked with 20percent N,N'-bisacryloylpiperazine.In this paper, we show that lowering the degree of crosslinking and diluting piperidone sites inside the polymeric matrix by copolymerisation with an inactive comonomer (N-acryloylmrpholine), decrease catalyst degradation and improve average reactivity ofcatalytic sites.The best results were obtained with a 5percent crosslinked resin containing 15percent piperidin-4-one sites.With the same proportions, we prepared a polymer-supported chiral ketone 14 which catalyzes the enantioselective hydration of α-aminobenzylacetonitrile. Key words: α-aminonitrile / α-aminoamide / enantioselective hydration / polamer-supported catalysis / ketonic resins
- Taillades, J,Garrel, L.,Lagriffoul, P. H.,Commeyras, A.
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p. 191 - 198
(2007/10/02)
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- Method of treating inflammation, allergy, asthma and proliferative skin disease using heterocyclic amides
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The compounds of this invention are heterocyclic amides represented by the formula: STR1 wherein: R1 R2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a STR2 group wherein q, r and t are independently an integer of from 1 to 8 provided that q+r+t is equal to or less than 10; y is thio, sulfinyl or sulfonyl; Alk is straight or branched chain lower alkylene, and R3 is a heterocyclic amine represented by the formula: STR3 wherein R4 is selected from the group consisting of hydrogen, lower alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl, carboxyl or carboxyloweralkyl; X is selected from the group consisting of N--R4, O and CH2 ; m is 2 or 3; n is 2 or 3 when X is O or N--R4, and n is 1 to 3 when x is CH2 ; p is 0 to 2; and the pharmaceutically acceptable salts thereof. The compounds are anti-inflammatory and anti-allergy agents.
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- SYNTHESIS OF γ-KETOAMIDES VIA NUCLEOPHILIC ATTACK ON IRON TETRACARBONYL COMPLEXES OF α,β-UNSATURATED AMIDES
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Organolithium and Grignard reagents react with the readily-formed iron tetracarbonyl complexes of α,β-unsaturated amides to give γ-ketoamides in good yield via acyl transfer from the metal to the β carbon of the α,β-unsaturated amide.
- Pouilhes, Annie,Thomas, Susan E.
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p. 2285 - 2288
(2007/10/02)
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