6066-83-7Relevant academic research and scientific papers
Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources
Nauth, Alexander M.,Konrad, Tim,Papadopulu, Zaneta,Vierengel, Nina,Lipp, Benjamin,Opatz, Till
supporting information, p. 4217 - 4223 (2018/09/29)
In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers higher flexibility instead. Such a setting was used for the cyanation of iminium ions with a variety of different easy-to-handle HCN sources such as hexacyanoferrate, acetonitrile or α-amino acids. The latter substrates were first converted to their corresponding nitriles through oxidative decarboxylation. While glycine directly furnishes HCN in the oxidation step, the aliphatic nitriles derived from α-substituted amino acids can be further converted into the corresponding cyanohydrins in an oxidative C-H functionalization. Mn(OAc)2 was found to catalyze the efficient release of HCN from these cyanohydrins or from acetone cyanohydrin under acidic conditions and, in combination with the two previous transformations, permits the use of protein biomass as a non-toxic source of HCN.
SPIROHYDANTOIN COMPOUNDS AND THEIR USE AS SELECTIVE ANDROGEN RECEPTOR MODULATORS
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Page/Page column 82, (2013/09/12)
The present invention relates to a compound of formula (1-1 ) in free form or in pharmaceutically acceptable salt form in which the substituents are as defined in the specification; to its preparation, to its use as a medicament and to medicaments comprising it. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
Poly(diiododiacetylene): Preparation, isolation, and full characterization of a very simple poly(diacetylene)
Luo, Liang,Wilhelm, Christopher,Sun, Aiwu,Grey, Clare P.,Lauher, Joseph W.,Goroff, Nancy S.
, p. 7702 - 7709 (2008/12/22)
Poly(diiodiacetylene), or PIDA, is a conjugated polymer containing the poly(diacetylene) (PDA) backbone but with only iodine atom substituents. The monomer diiodobutadiyne (1) can be aligned in the solid state with bis(nitrile) oxalamide hosts by hydrogen bonds between oxalamide groups and weak Lewis acid-base interactions (halogen bonds) between nitriles and iodoalkynes. The resulting cocrystals start out pale blue but turn shiny and copper-colored as the polymerization progresses. The development of a crystallization methodology that greatly improves the yield of PIDA to about 50% now allows the full characterization of the polymer by X-ray diffraction, solid-state 13C MAS NMR, Raman, and electron absorption spectroscopy. Comparison of a series of hosts reveals an odd-even effect in the topochemical polymerization, based on the alkyl chain length of the host. In the cocrystals formed with bis(pentanenitrile) oxalamide (4) and bis(heptanenitrile) oxalamide (6), the host/guest ratio is 1:2 and the monomer polymerizes spontaneously at room temperature, while in the case of bis(butanenitrile) oxalamide (3) and bis(hexanenitrile) oxalamide (5), where the host and guest form cocrystals in a 1:1 ratio, the polymerization is disfavored and does not go to completion. The topochemical polymerization can also be observed in water suspensions of micrometer-sized 6.1 cocrystals; the size distribution of these microcrystals, and the resulting polymer chains, can be controlled by sonication. Completely polymerized PIDA cocrystals show a highly resolved vibronic progression in their UV/vis absorption spectra. Extensive rinsing of the crystals in organic solvents such as methanol, THF, and chloroform separates the polymer from the soluble host. Once isolated, PIDA forms blue suspensions in a variety of solvents. The UV/vis absorption spectra of these suspensions match the cocrystal spectrum, without the vibronic resolution. However, they also include a new longer-wavelength absorption peak, associated with aggregation of the polymer chains.
Radical reduction of aromatic azides to amines with triethylsilane
Benati, Luisa,Bencivenni, Giorgio,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Scialpi, Rosanna,Spagnolo, Piero,Zanardi, Giuseppe
, p. 5822 - 5825 (2007/10/03)
Aromatic azides are inert toward triethylsilane under thermal conditions in the presence of a radical initiator, but in the presence of additional catalytic amounts of tert-dodecanethiol, they afford anilinosilanes and thence the corresponding anilines in virtually quantitative yields.
New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity
Yuan, Hai,Silverman, Richard B.
, p. 1331 - 1338 (2007/10/03)
A series of potential substrates of γ-aminobutyric acid aminotransferase (GABA-AT) with lipophilic bioisosteres of the carboxylic acid group (2-7) were synthesized and tested. Most of the synthesized compounds showed substrate activities with GABA-AT; 1H-tetrazole-5-propanamine (6) was the best of those tested. The potential time-dependent inhibitor of GABA-AT, 1H-tetrazole-5-(α-vinyl-propanamine) (8), was designed based on the structures of 6 and the antiepilepsy drug vigabatrin (4-aminohex-5-enoic acid, 1). The synthesized compound 8 showed time-dependent inhibition of GABA-AT, but its potency is lower than that of vigabatrin. Methylation of the tetrazole group in 8 resulted in loss of time-dependent activity, suggesting that the tetrazole ring, the carboxylate bioisostere, exists in its deprotonated form in the enzyme active site.
One-pot sequence for the decarboxylation of α-amino acids
Laval, Gilles,Golding, Bernard T.
, p. 542 - 546 (2007/10/03)
Treatment of an α-amino acid with N-bromosuccinimide in water at pH 5 or in an alcoholic-aqueous ammonium chloride mixture, followed by addition of nickel(II) chloride and sodium borohydride, effected an overall decarboxylation via an intermediate nitrile to afford the corresponding amine in good yield.
Additions of azomethine ylides to fullerene C60 assisted by a removable anchor
Da Ros, Tatiana,Prato, Maurizio,Lucchini, Vittorio
, p. 4289 - 4297 (2007/10/03)
The addition of nitrile oxides to [60]fullerene, leading to isoxazolinofullerenes, can be reversed using reducing agents such as Mo(CO)6 or DIBALH. Thus, this reaction can be used; in principle, for protection/deprotection of [60]fullerene or f
Aminomethylation of functionalized organozinc reagents and grignard reagents using immonium trifluoroacetates
Millot, Nicolas,Piazza, Claudia,Avolio, Salvatore,Knochel, Paul
, p. 941 - 948 (2007/10/03)
New immonium trifluoroacetates 1 and 2 react readily with functionalized organozinc or magnesium reagents leading to the corresponding aminomethylated products of type 5 and 7. The resulting bis-allylamines were deallylated leading to primary amines.
KINETICS OF OXIDATION OF AMINO ACIDS BY QUINOLINIUM DICHROMATE
Karim, E.,Mahanti, M. K.
, p. 1471 - 1476 (2007/10/02)
The kinetics of oxidation of amino acids (lysine, arginine and histidine) by quinolinium dichromate, in acid medium, at constant ionic strength, has been investigated.The reactions were first order each in substrate, oxidant and acid concentrations.Under the experimental conditions used, the reaction proceeded by the way of the cationic form of the amino acids.The absence of a kinetic isotope effect indicated that there was no cleavage of the carbon-hydrogen bond in the rate determining step.
Reduction d'azides par la triphenylphosphine en presence d'eau : une methode generale et chimioselective d'acces aux amines primaires
Knouzi, Noureddine,Vaultier, Michel,Carrie, Robert
, p. 815 - 819 (2007/10/02)
The reaction of azides with one equivalent of triphenylphosphine in the presence of a slight excess of water in THF leads quantitatively to the corresponding primary amines.This transformation is chemoselective.
