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The reaction of allyl(furfuryl)amines with aroyl isothiocyanates was studied. The reaction proceeded via an initial nucleophilic addition of the allylamine nitrogen atom to isothiocyanates and a subsequent spontaneous intramolecular Diels–Alder reaction involving the furan ring of intermediate N-allyl-N-furfurylthioureas with the formation of a single diastereomer of 3a,6-epoxyisoindoles. [ABSTRACT FROM AUTHOR]

In this study, 2-acrylamido-2-methyl-1-propane sulfonic acid (AMPS) and allylamine (AA) were copolymerized in an aqueous solution via free radical polymerization using ammonium persulfate as the initiator. The chemical structure and compositions of the copolymers were confirmed by elemental analysis, Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance spectroscopy (NMR). Monomer reactivity ratios were determined by Fineman-Ross (rAMPS = 0.91 ± 0,01 and rAA = 0.40 ± 0.02), Kelen-Tudos (rAMPS = 1.10 ± 0.02 and rAA = 0.45 ± 0.01) and inverted Fineman-Ross (rAMPS = 0.85 ± 0.01 and rAA = 0.31 ± 0.03) methods. AMPS was found to be more reactive than AA and copolymers had a random composition. The flocculation performance of the copolymer was evaluated in Fe(OH)3 hydrosol. When the concentration of the copolymer in the hydrosol was more than 15 mg/L, the concentration of Fe3+ ions decreased up to 15 times due to flocculation of hydrosol particles. Effect of the concentration of AMPS-AA copolymer on the electropotential (zeta) and particle size of the hydrosol Fe(OH)3 were also studied systematically. It was determined that the zeta potential of the particles decreased from + 58 to + 20 mV and the average particle size of the hydrosol increased approximately 30 times when copolymer concentration in the hydrosol reached to 20 mg/L. [ABSTRACT FROM AUTHOR]

Polyelectrolytes show complexation by the other polymers having opposite charges. Allyamine (AlAm) is a cationic monomer, and vinyl sulfonic acid (VSA) is an anionic monomer. AlAm and its copolymer with VSA are excellent polyelectrolytes that can be used in aqueous systems. In this work, we aimed to synthesize the allylamine hydrochloride-vinyl sulfonic acid (AlAm.HCl/VSA) copolymers in different mole ratios on feed composition by the free radical polymerization method at 50 °C for 50 h with a thermal initiator 2,2'-azo-bis(2-methylpropanediamine) dihydrochloride. Furthermore, we aimed to obtain copolymer compositions by FT-IR, Raman, and NMR spectroscopy methods. Because of the overlapping obtained peaks from the mentioned methods above, we used Elemental analysis. The monomer reactivity ratios were calculated by Fineman-Ross (FR), Kelen-Tudos (KT), Mayo-Lewis (ML), and Inverted Fineman-Ross (iFR) methods. These ratios were calculated for AlAm.HCl and VSA as r1 = 0.3613 and r2 = 1.0896 via FR method; r1 = 0.3731 and r2 = 1.1169 by the KT method; r1 = 0.3574 and r2 = 1.0552 via ML method; and r1 = 0.3375, r2 = 1.0772 by the iFR method, respectively. Deacidified copolymer is obtained in (38.369:61.631) actual composition (AlAm/VSA) at 2.9 molar sodium hydroxide solution in methanol. In an evaluation of the kinetic behavior of (38.369:61.631) in actual composition, it is shown that the copolymer conversion rate is a kind of second-order reaction. For investigation of structural behavior, Raman- FT-IR–NMR (1H, 13C, DEPT135, Cosy) was used. Thermal properties were investigated by thermal gravimetry analysis (TGA). [ABSTRACT FROM AUTHOR]

The reaction of 5-arylisoxazolyl- and 4,5-dichloroisothiazolylallylamines with pyromucic acid chlorides (2-furoyl and 5-methyl-2-furoyl chlorides) was studied. The reaction proceeds via the initial acylation of the allylamine nitrogen atom and the subsequent spontaneous intramolecular Diels–Alder reaction involving the furan ring of intermediate N-furoylamides with the formation of a single diastereomer of 3a,6-epoxyisoindol-3-ones. [ABSTRACT FROM AUTHOR]

A number of new pyrazole and pyrimidine derivatives containing an allylmorpholine fragment were obtained by reactions of chromone-containing allylmorpholines with 1,2- and 1,3-binucleophiles (hydrazine, guanidine, acetamidine). The syntheses were carried out under mild conditions (ethanol, room temperature), and the target products were isolated with high yields. The obtained compounds are of interest as potential cholinesterase inhibitors. [ABSTRACT FROM AUTHOR]

A concise route for the preparation of two simple optically pure indolizidin-5-ones has been developed. The key chain elongation process was achieved using a triethylborane/catechol mediated hydroalkylation of Boc-protected 2-vinylpyrrolidines. By using complementary strategies, these two bicyclic lactams can be alkylated with complete control of the stereochemistry at C(5) and their conversion to a variety of indolizidine alkaloids such as coniceine, indolizidine 209D and 167B, 5-epi-indolizidine 249A and monomorine has been reported in the literature. [ABSTRACT FROM AUTHOR]

Stereospecific α-amination has been accomplished via addition of N-phenyltriazolinedione (PhTAD) to the allylic position of dihydropyrroles. The aim of this study is to evaluate new PhTAD derivatives of biologically active bicyclic dihydropyrroles. Ene reaction was accomplished via addition of PhTAD to the allylic position to react with syn and anti diastereomers for α-amination. The α-amination depends on the stereochemistry, proceeding faster with syn than anti diastereoisomers. Steric hindrance from sulfide substituent slows down the transformation. Although the results are in accordance with an ene reaction followed by 1,3-shift of the urazole moiety, deuteration at the allylic position by simply stirring the diastereoisomeric dihydropyrroles in MeOD revealed a [1,3-H] shift. The stereospecificity of the transformation is attributed to steric hindrance during the allylic transposition step. [ABSTRACT FROM AUTHOR]

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Lupane C-28 monoallylamides with α-ketoxime and α-hydroxyoxime groups in ring A were prepared from betulonic acid. Formation of A-secolupane C-3(28) mono- and diallylamides was used as an example to demonstrate that a one-step synthesis of 2,3-secotriterpene amides was possible by fragmentation of betulin and betulonic acid α-oximes by oxalylchloride or thionylchloride with subsequent amidation of the 2,3-secotriterpenoic acids formed in situ by allylamine. The proposed method enabled the yield of 2,3-secolupane C-3,C-28 diamides to be increased by five times compared with the previously described five-step method for preparing A-secotriterpene amides from betulonic acid. [ABSTRACT FROM AUTHOR]

The present study demonstrated that covalently galactosylated poly( D,L-lactic- co-glycolic acid) (PLGA) surface encourages hepatocyte adhesion and growth to form a dense cell network. Galactosylation of the PLGA surface was accomplished by grafting allylamine (AA) using inductively coupled plasma-assisted chemical vapor deposition (ICP-CVD) and conjugating lactobionic acid (LA) with AA via 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide and N-hydroxysuccinimide (EDC/NHS) activation. The modified surface was characterized by Fourier transform infrared spectroscopy in the attenuated total reflectance, electron spectroscopy of chemical analysis, atomic force microscopy, and contact angle measurement. For evaluation of cell affinity in vitro, primary rat hepatocytes were prepared and seeded onto the modified PLGA surfaces. The galactosylated PLGA surface showed more pronounced hepatocyte adhesion and growth compared to those on the control PLGA surface. The hepatocytes seeded on galactosylated substrates exhibited a radial migration with filopodial growth to form multicellular aggregates, whereas those on control PLGA showed slowly adhered rounded shapes. Moreover, galactosylation increased metabolic hepatocyte activities such as albumin secretion and urea synthesis. [InlineMediaObject not available: see fulltext.] [ABSTRACT FROM AUTHOR]

This article describes the novel possibility of the polyester (polyethylene terephthalate) surface modification by plasma treatment. Moreover, this modified polyester could be component for the composite material (with hyaluronic acid) used in the wound healing. In this study, the experimental methods: FT-IR spectroscopy, the contact angle measurement, X-ray photoelectron spectroscopy and scanning electron microscopy were used for the surface modified polyester characterisation. [ABSTRACT FROM AUTHOR]

A new organic-inorganic hybrid polyphosphazene polymer was synthesized via sequential nucleophilic substitution using allylamine and phenol. The polymer was characterized by FTIR, 1H-NMR, and 31P-NMR spectra. The thermal properties were studied by DSC and TGA. It was found that the polymer has good thermal stability. Char yields of the polymer reaches to 48.6% at 800°C. The high char yield makes it possible in theory for the polymer to be used as flame retardant. By cross linking, the thermal stability of the polymer could be improved further. [ABSTRACT FROM AUTHOR]

Reductive amination of 3-deoxy-D-manno-octulosonic acid (Kdo) with allylamine (AllN) or 2-(4-aminophenyl)ethylamine (APEA) yields epimer pairs of 2-N-allylamino and 2-N-[2-(4-aminophenyl)ethylamino]-2,3-dideoxy-D-glycero-D-galacto- and-2,3-dideoxy-D-glycero-D-talo-octonic acid. The yields were 50–60% due to reduction of Kdo to the respective polyols as side reaction products. Mass spectrometric analyses proved the amination derivatives to be the expected glycamines. Nuclear magnetic resonance (NMR) studies were performed on 2-N-allylamino-2,3-dideoxyoctonic acid which represents the chain terminus of allylaminated oligosaccharides derived from bacterial lipopolysaccharides (LPS) after acid hydrolysis and reductive allylamination. [ABSTRACT FROM AUTHOR]

This study measures the inhibition of [H]uridine uptake by smooth muscle cells to determine sublethal toxic injury by the cardiovascular toxins, allylamine, isoproterenol, and β-aminopropionitrile. The exposure period or the concentration of toxin which inhibited 30% of [H]uridine uptake by smooth muscle cells could be utilized as an endpoint for ranking toxicity. Cytotoxicity of the three toxins to smooth muscle cells were ranked as: allylamine > isoproterenol > β-aminopropionitrile. Recovery of cells utilizing [H]uridine uptake inhibition as a method for assessing comparative cytotoxicity and for screening of agents potentially injurious to vascular cells. [ABSTRACT FROM AUTHOR]

Enantioselective isomerizations of allylamines to enamines are summarized from idea to industry. The Rh–BINAP catalyst reveals high selectivities, 99% yield and 98% enantiomer excess and high activity, TON > 400,000. Its industrial use for the production of a 1,500 t/y scale of (–)-menthol is introduced emphasizing technical development. [ABSTRACT FROM AUTHOR]

Oxidation of 1,2,4,5-tetrafluoro-3,6-bus (vinylthio)benzene (1) affords 1,2,4,5-tetra fluoro3,6-bis(vinylsulfonyl)benzene (2) in 65 % yield. The reaction of compound 2 with allylamine gives a new heterocyclic compound, 5,6-difluorobenzo-[ a,d]-bis(3,3′-dihydro-l,l′-sulfonylallyl-4,4′-perhydroazine) (3). This compound is the product of nucleophilic addition at the vinylsulfonyl group and intramolecular replacement of fluorine atoms of the benzene ring. The structure of compound 3 has been established by X-ray structural study. [ABSTRACT FROM AUTHOR]