7500-45-0Relevant articles and documents
Recyclization reactions of 1-alkylpyrimidinium salts
Vardanyan, Ruben S.,Danagulyan, Gevork G.,Mkrtchyan, Armen D.,Hruby, Victor J.
, p. 129 - 133 (2011)
The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide ( 3 ) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4- hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde ( 5 ). Heating of the same pyri
Reductive N-alkylation of primary amides using nickel-nanoparticles
Alenad, Asma M.,Alshammari, Ahmad S.,Jagadeesh, Rajenahally V.,Murugesan, Kathiravan,Sohail, Manzar
, (2021/11/22)
Here we report Ni-nanoparticles as reusable catalysts for reductive N-alkylation of amides. These Ni-nanoparticles based catalysts have been prepared by the template synthesis of tartaric acid and 2-methyl imidazole ligated Ni-complex on SiO2 and subsequent pyrolysis under argon. Applying optimal Ni-nanostructured catalyst, N-alkylation of aromatic and heterocyclic primary amides with different aldehydes in presence of molecular hydrogen was performed to access structurally diverse N-alkylated amides in good to excellent yields. In addition, the applicability of this N-alkylation protocol has been demonstrated for the selective functionalization of primary amide group in Levetiracetam drug.
Method for preparing amide compounds through ionic liquid catalysis in high-pressure environment
-
Paragraph 0051-0054, (2021/01/24)
The invention relates to a method for preparing amide compounds through ionic liquid catalysis in a high-pressure environment. According to the method, ionic liquid 1-ethyl-3-methylimidazolium acetateis used as a catalyst and a solvent, oxygen is used as an oxidizing agent, and aromatic methanol or alkyl alcohol is converted into an amide compound under the conditions of high pressure and heating. The synthesis method provided by the invention has the advantages that the raw material and technical cost is low; compared with other traditional methods, the method is safe, low in toxicity, economical and environmentally friendly; and the method has few steps, is simple and convenient to operate, is beneficial to large-scale synthesis, and has important significance for synthesis of amide compounds and large-scale industrialization of preparation.
Dehydrative Beckmann rearrangement and the following cascade reactions
Liu, Yinghui,Wei, Yongjiao,Xie, Lan-Gui
supporting information, (2021/11/16)
The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.
Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids
Ramachandran, P. Veeraraghavan,Hamann, Henry J.
supporting information, p. 2938 - 2942 (2021/05/04)
Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.
Efficient and accessible silane-mediated direct amide coupling of carboxylic acids and amines
D'Amaral, Melissa C.,Jamkhou, Nick,Adler, Marc J.
supporting information, p. 288 - 295 (2021/01/28)
A straightforward method for the direct synthesis of amides from amines and carboxylic acids without exclusion of air or moisture using diphenylsilane with N-methylpyrrolidine has been developed. Various amides are made efficiently, and broad functional group compatibility is shown through a Glorius robustness study. A gram-scale synthesis demonstrates the scalability of this method. This journal is
Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ2-(C,S)?Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine
Achard, Thierry,Bellemin-Laponnaz, Stéphane,Chen, Weighang,Egly, Julien,Maisse-Fran?ois, Aline
supporting information, (2022/01/20)
Amide synthesis is one of the most crucial transformations in chemistry and biology. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcohols with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an additional ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η6-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i. e. 3 c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained.
Synthesis of Bench-Stable N-Quaternized Ketene N, O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis
McConnell, Danielle L.,Blades, Alisha M.,Rodrigues, Danielle Gomes,Keyes, Phoebe V.,Sonberg, Justin C.,Anthony, Caitlin E.,Rachad, Sofia,Simone, Olivia M.,Sullivan, Caroline F.,Shapiro, Jonathan D.,Williams, Christopher C.,Schafer, Benjamin C.,Glanzer, Amy M.,Hutchinson, Holly L.,Thayaparan, Ashley B.,Krevlin, Zoe A.,Bote, Isabella C.,Haffary, Yasin A.,Bhandari, Sambat,Goodman, Jack A.,Majireck, Max M.
, p. 13025 - 13040 (2021/09/28)
N-Quaternized ketene N,O-acetals are typically an unstable, transient class of compounds most commonly observed as reactive intermediates. In this report, we describe a general synthetic approach to a variety of bench-stable N-quaternized ketene N,O-acetals via treatment of pyridine or aniline bases with acetylenic ethers and an appropriate Br?nsted or Lewis acid (triflic acid, triflimide, or scandium(III) triflate). The resulting pyridinium and anilinium salts can be used as reagents or synthetic intermediates in multiple reaction types. For example, N-(1-ethoxyvinyl)pyridinium or anilinium salts can thermally release highly reactive O-ethyl ketenium ions for use in acid catalyst-free electrophilic aromatic substitutions. N-(1-Ethoxyvinyl)-2-halopyridinium salts can be employed in peptide couplings as a derivative of Mukaiyama reagents or react with amines in nucleophilic aromatic substitutions under mild conditions. These preliminary reactions illustrate the broad potential of these currently understudied compounds in organic synthesis.
Tuning catalysis of boronic acids in microgels by: In situ reversible structural variations
Zhai, Zhenghao,Du, Xue,Wu, Qingshi,Zhu, Lin,Farooqi, Zahoor H.,Li, Jin,Lan, Ruyue,Wang, Yusong,Wu, Weitai
, p. 3734 - 3744 (2020/02/04)
The catalysis of boronic acids immobilized in polymer microgels can be modulated by bubbling with N2/CO2 gas, and in some cases by adding glucose, making their catalytic activity comparable or even superior to that of the corresponding free boronic acid monomers homogeneously dispersed in solutions and, more importantly, making these boronic-acid-containing polymer microgels able to catalyze alternate reactions that may extend the usefulness. This enhanced catalytic function of these boronic-acid-containing microgels as organoboron acid catalysts is plausibly achieved via in situ reversibly structural variations. Kinetic studies have been carried out on the model boronic-acid-catalyzed aza-Michael addition, aldol, amidation, and [4 + 2] cycloaddition reactions in order to better understand the catalytic process.
Direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2
Wang, Hui,Dong, Wei,Hou, Zhipeng,Cheng, Lidan,Li, Xiufen,Huang, Longjiang
, (2020/02/15)
This paper described a mild and efficient direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2. Arylacetic acid derivatives reacted with different amines to afford the corresponding amides in good to excellent yield except of aniline. Aryl formic acids failed to react with aniline but smoothly reacted with aliphatic amines and benzylamine in moderate to good yield, fatty acids reacting with benzyl and aliphatic amines give amides in good to excellent yield. Chiral amino acids derivatives were transformed into amides without racemization in moderate yield. The possible mechanism of direct amidation catalyzed by TiCp2Cl2 was discussed. This catalytic method is very suitable for the amidation of low sterically hindered arylacetic acid, fatty acids with different low sterically hindered amines except aniline, as well as the amidation of aryl formic acid with benzyl and aliphatic amines.
