New nitrogen-containing<Emphasis Type="Italic">α</Emphasis>-oxides

N-(2,3-Epoxypropyl)-α-pyrrolidone and N-(2,3-epoxypropyl)-α-suecinimide have been obtained for the first time. It has been shown that N-(2,3-epoxypropyl)-α-pyrrolidone readily reacts with ammonia and diethylamine to form the corresponding amino alcohols.     

Some transformations of N-(2,3-epoxypropyl)-1,8-naphthosultam

A method of synthesis has been developed for N-(2,3-epoxypropyl)-1,8-naphthosultam and some transformations of this compound were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 236–242, February, 2000.     

New nitrogen-containingα-oxides

N-(2,3-Epoxypropyl)--pyrrolidone and N-(2,3-epoxypropyl)--suecinimide have been obtained for the first time. It has been shown that N-(2,3-epoxypropyl)--pyrrolidone readily reacts with ammonia and diethylamine to form the corresponding amino alcohols.     

Synthesis of Branched Hydrazones by Reaction of N-(2,3-Epoxypropyl) Derivatives of Hydrazones with Benzenediols

A series of branched hydrazones have been prepared by reaction of N-(2,3-epoxypropyl) derivatives of 9-ethyl-3-carbazolecarbaldehyde and 4-diethylamino-benzcarbaldehyde phenylhydrazones with 1,2-, 1,3-, and 1,4-benzenediols. It was found that the reaction rate depends on the polarity of solvents.     

Reactions of vinyl 2,3-epoxypropyl ethers with 4,5-dihydro-1H-pyrazoles

Reactions of vinyl 2,3-epoxypropyl ether and 2-(vinyloxy)ethyl 2,3-epoxypropyl ether with 4,5-dihydro-1H-pyrazoles give, respectively, 3-vinyloxy-1-(4,5-dihydro-1H-pyrazol-1-yl)propan-2-ols and 3-(2-vinyloxyethoxy)-1-(4,5-dihydro-1H-pyrazol-1-yl)propan-2-ols in 70–91% yield.     

Reactions of diarylamines with hexafluoroacetone

Diphenylamine reacts with hexafluoroacetone to give a mixture of products, of which 2-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)diphenylamine (II) was isolated. N-Arylanthranilic acids modify the 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl group upon the reaction of its sodium salt with the hydrate of hexafluoroacetone (I) under mild conditions. This method gave 4-(1-hydroxy-1-trifluoromethyl-2,2,3-trifluoroethyl)-N-(2,3-xylyl)anthranilic acid from N-(2,3-xylyl)anthranilic acid in 93% yield.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 952–954, April, 1991.     

Gas chromatographic properties of methacrylate polymers modified by silver nanoparticles

Russian Chemical Bulletin - The gas chromatographic properties of the porous methacrylate polymers, copolymers of 2,3-epoxypropyl methacrylate (2,3-EPMA) and ethylenedimethacrylate (EDMA), modified...     

Role of Epoxides in the Oxidation of Allyl Alcohol,Allyl Formate,and Allyl Acetate in Acetic Acid

The formation of epoxy derivatives as intermediate products in the oxidation of allyl alcohol, allylformate, allyl acetate in acetic acid was proved. Intermediate epoxy compounds undergo further trans-formations: They react with acetic acid to give glycerol esters or are converted into polyethers of glyceroland its esters. The rate constants for transformations of 2,3-epoxypropanol, 2,3-epoxypropyl formate, and 2,3-epoxypropyl acetate along these pathways were measured. Higher selectivity of glycerol ester formation from allyl formate was substantiated.     

Polymers from siloxane-containing epoxides

The synthesis and polymerization of seven epoxy polymer precursors which contained the siloxane linkage in varying structural arrangements was carried out. The polymers prepared from such precursors have utility as embedding compounds for electrical circuits. Polymerization of these epoxy intermediates with siloxane-containing diamines resulted in solid, thermosetting materials for which dielectric data were obtained. Dielectric constants of 3.1 were measured at 1 keps for polymers prepared by polymerization of 1,9-bis[p-(2,3-epoxypropyl)phenyl]decamethylpentasiloxane with 1,3-bis(p-am-inophenoxy)tetramethyldisiloxane, whereas polymers derived from 1,4-bis{[p-(2,3-epoxypropyl)phenyldimethylsiloxy]dimethylsilyl}benzene and the same diamine were characterized by slightly higher dielectric constants and a high degree of toughness, being nonbrittle at ?50°C.     

Porous DMN-co-GMA copolymers modified with 1-(2-hydroxyethyl)-2-pyrrolidone

Journal of Thermal Analysis and Calorimetry - Porous microspheres obtained from 2,3-epoxypropyl methacrylate (GMA) and 1,4-di(methacryloyloxymethyl) naphthalene (DMN) were modified by the reaction...     

Reactions of 3-Substituted 1,2-Epoxypropanes with Pyridinium Salts. N-Alkylpyridinium Salts and Their Synthetic Potential

1-Chloro-2,3-epoxypropane and 2,3-epoxypropyl carboxylates react with pyridinium carboxylates and phosphonates, yielding N-alkylated pyridinium salts.     

The first stereoselective synthesis of (+)-nuciferol and (+)-nuciferal

Using (S)-benzyl 2,3-epoxypropyl ether (1), the first stereoselective synthesis of (+)-nuciferol (14) and (+)-nuciferal (16) has been achieved. Employing the same methodology an enantioselective synthesis of (+)--curcumene (17) is also described.     

Synthesis of α-phthalimido-α′-dithiocarbamato propan-2-ols via a one-pot,three-component epoxide ring-opening in water

Regioselective ring-opening of the N-(2,3-epoxypropyl)phthalimide with in situ prepared dithiocarbamic acid in water is reported for the synthesis of a new family of α-phthalimido-α′-dithiocarbamato propan-2-ols. The present method is simple, EtOAc is used for work-ups and affords excellent yield of products.     

Heterocyclization of Functionalized Heterocumulenes with C,N- and C,O-Binucleophiles. 1. Cyclocondensation of 1-Chloroalkylheterocumulenes and N-(1-Chloroalkylidene)urethanes with 2-Cyanomethylpyridine

The interaction of 1-chloroalkyl isocyanates, 1-chloroalkylcarbodiimides, 1,1-dichloroalkyl isocyanates, and N-(1-chloroethylidene)-O-methylurethanes with 2-cyanomethylpyridine has been investigated. An effect of organic base has been detected on the regioselectivity of the cyclocondensation of 1-chloroalkyl isocyanates, which leads to 2,3-dihydro-1H-pyrido[1,2-c]pyrimidin-1-one or the isomeric 2,3-dihydro-1H-pyrido[1,2-c]pyrimidin-3-one. Irrespective of the cyclization conditions 1-chloroalkylcarbodiimides react with the formation of 1-imino-2,3-dihydro-1H-pyrido[1,2-c]pyrimidines. One type of product, a 1H-pyrido[1,2-c]pyrimidin-1-one, was also isolated from 1,1-dichloroalkyl isocyanates and N-(1-chloroalkylidene)urethanes.     

Synthesis and Crystal Structure of N-（2-（1,3,4-oxadiazol-2-yl）phenyl）-2,3-dimethylaniline

The title compound, N-（2-（1,3,4-oxadiazol-2-yl）phenyl）-2,3-dimethylaniline, was synthesized and studied by single-crystal X-ray diffraction method. The structure of the product was confirmed by IR, ^1H- and ^13C-NMR spectroscopy, elemental analysis and mass spectrometry. These experimental studies were supported by theoretical optimizations.     

Monodisperse polymer beads as packing material for high-performance liquid chromatography. Preparation of macroporous poly(2,3-epoxypropyl vinylbenzyl ether-co-divinylbenzene) beads,their properties,and application to HPLC separations

In search for HPLC separation media with new surface chemistries, a styrene-based monomer, 2,3-epoxypropyl vinylbenzyl ether, containing reactive epoxide groups has been syn-thesized and copolymerized with divinylbenzene in a suspension polymerization. The process involves the use of size monodisperse particles that are swollen with monomer and then polymerized in the presence of a porogenic diluent consisting of a mixture of 4-methyl-2-pentanol and octane. The effect of concentration of divinylbenzene on the pore size dis-tribution and the specific surface area of the resulting uniformly sized porous poly(2,3-epoxypropyl vinylbenzyl ether-co-divinylbenzene) beads has been studied. The epoxide groups of the copolymer have been hydrolyzed and the beads used for reversed-phase chro-matography of both small molecules and proteins to show the effect of hydrophobicity of the matrix on the separation properties. Reversed-phase chromatography of alkylbenzenes follows the expected pattern while for proteins the hydrolyzed beads with the highest content of the crosslinking monomer exhibit a remarkable deviation from the predicted retention characteristics. © 1995 John Wiley & Sons, Inc.     

Synthesis of the F11334's from o-prenylated phenols: muM inhibitors of neutral sphingomyelinase (N-SMase)

F11334A(1), F11334A(2), F11334A(3), and their corresponding resorcinol analogs were synthesized along with F11334B(1), and F11263. In the course of these synthetic studies, several conditions for manipulating (2,3-propanediol) and (2,3-epoxypropyl) o-substituted phenols were developed as well as a variety of conditions for cleavage of aryl O-t-butyl carbonates. From enzyme assays it appears that the hydroquinone nucleus is the essential structural necessary for N-SMase inhibition. Furthermore, it appears that this family of compounds is comprised of irreversible inhibitors.     

NMR Study of the Structure of Polymers Based on 2,3-Epoxypropyl Methacrylate

The structure of homo- and copolymers of 2,3-epoxypropyl methacrylate and methyl methacrylate was studied by high-resolution NMR. The stereochemical sequences in the polymer chains were established.     

Reaction of 2,3-Epoxypropyl Ethers with 1-Butanol

Nucleophilic opening of the oxirane ring in 2,3-epoxypropyl ethers with alcohols in the presence of titanium alkoxides and other catalysts was studied. The mechanism of catalysis by titanium alkoxides was discussed on the basis of comparison with acid–base catalysts.     

The elucidation of the 1H- and 13C-NMR spectra of bis[N,N-di(2,3-epoxypropyl)-4-aminophenyl]methane (TGMDA) and composite with bis(4-animophenyl)sulfone (DDS) using two-dimensional fourier transform techniques

The application of Fourier transform (FT) two-dimensional nuclear magnetic resonance spectroscopy to the study of the composite of bis[N,N-di(2,3-epoxypropyl)-4-aminophenyl] methane (TGMDA) and the curing agent bis(4-aminophenyl)sulfone (DDS) is discussed. The combination of 2D-J resolved and homonuclear (proton) shift correlated experiments permits the complex proton spectrum due to the glycidylamine moiety to be completely elucidated. The potential utility of this in the study of the aging of prepreg is briefly discussed.