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Copper-catalyzed amination of aryl and alkenyl electrophiles

The copper-catalyzed arylation and vinylation of nitrogen nucleophiles is a highly versatile method for the construction of sp2C?N bonds. Copper-catalyzed C?N bond formation has an extensive history and the field has been reinvigorated with the development of ligand-promoted catalyst systems that provide general and effective reactions under relatively mild conditions. Copper promotes arylation and vinylation of a wide range of nitrogen nucleophiles, including amines, nitrogen heterocycles, and amide derivatives. The reactivity profile is complementary to that of palladium and often offers orthogonal chemoselectivity. This chapter presents a thorough overview of the copper-catalyzed coupling of aryl and vinyl halides with nitrogen nucleophiles. Current understanding of the mechanism of this process is presented along with a detailed overview of the scope and limitations of this reaction along with optimal reaction conditions for the coupling of various nitrogen nucleophile classes.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H975NO – PubChem

 

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 497-25-6, molcular formula is C3H5NO2, introducing its new discovery. 497-25-6

DIHYDROPYRIDINE NPY ANTAGONISTS: PIPERAZINE DERIVATIVES

A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of piperazine and homopiperazine derivatives of 4-phenyl-1,4-dihydropyridines of Formula (I). STR1 As antagonists of NPY-induced feeding behavior, these compounds are expected to act as effective anorexiant agents in promoting weight loss and treating eating disorders.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H202NO – PubChem

 

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Thermal Degradation Pathways of Aqueous Diamine CO2 Capture Solvents

Diamines have shown promise as CO2 capture solvents, yet very little is known about their pathway for thermal degradation. In this study, diamine thermal degradation was quantitatively monitored in lab-scale experiments on four aqueous diamine solvents; ethylenediamine (EDA) 1,2-propanediamine (1,2-DAP), 1,3-diaminopropane (1,3-DAP) and N-methyl-1,2-ethanediamine (N-MEDA), to gain a more comprehensive understanding of their degradation pathway(s). The major degradation products were identified by high resolution time-of-flight mass spectrometry (TOF-MS). Degradation pathways were proposed showing that the primary thermal degradation route for this class of amine are through carbamate formation followed by intermolecular cyclization to form an imidazolidinone or nucleophilic attack by a free amine to form a diamine urea.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1055NO – PubChem

 

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497-25-6, In heterogeneous catalysis, the catalyst is in a different phase from the reactants. At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 497-25-6, name is Oxazolidin-2-one. In an article£¬Which mentioned a new discovery about 497-25-6

Synthesis of stable derivatives of cycloprop-2-ene carboxylic acid

(Chemical Equation Presented) Large-scale syntheses of 3-(cycloprop-2-en-1- oyl)oxazolidinones from acetylene and ethyl diazoacetate are described. Unlike other cyclopropenes that bear a single substitutent at C-3, these compounds are stable to long-term storage. Although the cyclopropene derivatives are unusually stable, they are reactive toward cyclic and acyclic dienes in stereoselective Diels-Alder reactions.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1165NO – PubChem

 

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Synthesis and quantitative structure-activity relationship of fatty acid amide hydrolase inhibitors: Modulation at the N-portion of biphenyl-3-yl alkylcarbamates

Alkylcarbamic acid biphenyl-3-yl esters are a class of fatty acid amide hydrolase (FAAH) inhibitors that comprises cyclohexylcarbamic acid 3?-carbamoylbiphenyl-3-yl ester (URB597), a compound with analgesic, anxiolytic-like and antidepressant-like properties in rat and mouse models. Here, we extended the structure-activity relationships (SARs) for this class of compounds by replacing the cyclohexyl ring of the parent compound cyclohexylcarbamic acid biphenyl-3-yl ester (URB524) (FAAH IC50 = 63 nM) with a selected set of substituents of different size, shape, flexibility, and lipophilicity. Docking experiments and linear interaction energy (LIE) calculations indicated that the N-terminal group of O-arylcarbamates fits within the lipophilic region of the substrate-binding site, mimicking the arachidonoyl chain of anandamide. Significant potency improvements were observed for the beta-naphthylmethyl derivative 4q (IC50 = 5.3 nM) and its 3?-carbamoylbiphenyl-3-yl ester 4z (URB880, IC50 = 0.63 nM), indicating that shape complementarity and hydrogen bonds are crucial to obtain highly potent inhibitors.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H833NO – PubChem

 

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Lewis acid-promoted synthesis and reactivity of beta-O-benzylhydroxylamino imides derived from D-glyceraldehyde

This paper describes the synthesis and use beta-hydroxylamino imides derived from D-glyceraldehyde possessing a number of reactive sites that operate synergistically or alternatively to bring about highly regio- and diastereoselective transformations to give an optically pure aziridine-2-imide, a dihydro pyrimidine-2,4-dione, or a lactone. Both the syntheses, via the diastereoselective 1,4-conjugate addition of O-benzyl hydroxylamine to alpha,beta-unsaturated imides, and transformations can be simply tuned by choosing between different Lewis acids.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H398NO – PubChem

 

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Copper(I)-catalyzed highly regio- and stereoselective boron addition-protonolysis of alkynamides to give alkenamides

Copper-catalyzed and highly chemoselective reduction of N-alkynylamides by a boron addition-protonolysis protocol is presented. The reaction proceeds with the addition of boryl-copper complex to N-alkynylamides with high regioselectivity and stereoselectivity, followed by regiocontrolled transmetallation of the alpha-site of the alkenylboronate with MeOCuL to afford N-alkenylamides in good yields. Deuterium labeling experiments indicated that both of the alkenyl hydrogen atoms originate from the additive methanol. The copper-catalyzed semireduction of N-alkynylamides by a boron addition-protonlysis protocol afforded N-alkenylamides in good yields with high stereo- and chemoselectivity. Deuterium labeling experiments indicated that both of the alkenyl hydrogen atoms of the N-alkenylamides originate from the additive methanol. Copyright

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Oxazolidine – Wikipedia,
Oxazolidine | C3H602NO – PubChem

 

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497-25-6, A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 497-25-6, Name is Oxazolidin-2-one, molecular formula is C3H5NO2. In a Article, authors is Poindexter, Graham S.£¬once mentioned of 497-25-6

The Use of 2-Oxazolidinones as Latent Aziridine Equivalents. 2. Aminoethylation of Aromatic Amines, Phenols, and Thiophenols

The utility of 2-oxazolidinones 1 as latent, carboxylated aziridine functionalities was examined.Reaction of 2-oxazolidinone (1a), 3-methyl2-oxazolidinone (1b), 3-(phenylmethyl)-2-oxazolidinone (1c), 3-phenyl-2-oxazolidinone (1d) 4,4-dimethyl-2-oxazolidinone (1e), and 5-ethyl-2-oxazolidinone (1f) with aromatic amine salts, phenol, or thiophenols at elevated temperatures (> 130 deg C) afforded aminoethylated adducts.The aminoethylation occurred with concomitant loss of carbon dioxide to furnish variously substituted N-aryl-1,2-ethanediamines 4, 1-(2-phenoxyethyl)-2-imidazolidinone (8), or 2-(arylthio)ethanamines 9 on reactions of 1 with aromatic amine salts, phenol, and thiophenols, respectively.Imidazolidinone 8 is believed to be a secondary reaction product resulting from the condensation of the initially formed 2-phenoxyethanamine with starting oxazolidinone 1a.The aminoethylation reaction did not proceed with aliphatic amine hydrochlorides or alkyl mercaptans.Preliminary mechanistic pathways for these ring openings were also investigated employing a specific, C-5 deuterium-labeled oxazolidinone 1b-d2.Ring-opening experiments of 1b-d2 with N-methylaniline hydrochloride suggest reaction can occur through either a dioxazolinium 5 and/or 5 intermediate.In contrast, reaction of 1b-d2 with thiophenol suggests ring-opening to proceed only via the dioxazolinium pathway.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H907NO – PubChem

 

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Synthesis of unnatural amino acids from serine derivatives by beta-fragmentation of primary alkoxyl radicals

(Chemical Equation Presented) The fragmentation of primary alkoxyl radicals has been scarcely used in synthesis since other competing processes (such as oxidation or hydrogen abstraction) usually predominate. However, when serine derivatives were used as substrates, the scission took place in excellent yields. Tandem scission-allylation, -alkylation, or -arylation reactions were subsequently developed. This one-pot methodology was applied to the synthesis of unnatural amino acids, which are useful synthetic blocks or amino acid surrogates in peptidomimetics.

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Arylboronic acid-catalyzed direct condensation of carboxylic acids with ureas

The first example of the catalytic direct condensation of carboxylic acids with ureas to give N-acylureas, N,N?-diacyl-2-imidazolidones, and poly(N,N?-diacyl-2-imidazolidone)s is described. Arylboronic acids bearing electron-withdrawing substituents are highly effective as catalysts for this condensation. Furthermore, a new and efficient one-pot procedure for the conversion of carboxylic acids and urea to nitriles via N-acylurea intermediates was accomplished by using arylboronic acid and rhenium(VII) oxo complexes as hybrid catalysts.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H786NO – PubChem