6311-90-6Relevant academic research and scientific papers
Hydroamination of 2-vinylpyridine, styrene, and isoprene with pyrrolidine catalyzed by alkali and alkaline-earth metal complexes
Yakub,Moskalev,Bazyakina,Cherkasov,Shavyrin,Fedushkin
, p. 2887 - 2894 (2017)
The complexes (dpp-bian)Mg(thf)3, (dpp-bian)Ca(thf)4 and (dpp-bian)Mg(pyr)3 (dpp-bian is the 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene dianion; pyr is the pyrrolidine) catalyze the addition of pyrrolidine to 2-viny
Reversible C-N Bond Formation in the Zirconium-Catalyzed Intermolecular Hydroamination of 2-Vinylpyridine
Griffin, Samuel E.,Pacheco, Javier,Schafer, Laurel L.
supporting information, p. 1011 - 1016 (2019/03/08)
The intermolecular hydroamination of alkenes with alkylamines has been a long-standing challenge in catalysis, partially due to the near-thermoneutral nature of this transformation. Consistent with this understanding, we report the direct observation of reversible C-N bond formation in hydroamination. A bis(ureate) zirconium complex catalyzed the intermolecular hydroamination of 2-vinylpyridine. Reversible C-N bond formation was characterized by variable-temperature NMR spectroscopy, and thermodynamic parameters were determined using van't Hoff plots. Isolated intermediates support an aza-Michael-addition mechanism. Sensitivity to steric bulk in the C-N bond forming step provided further evidence for the kinetically accessible but limited thermodynamic driving force for this transformation.
Aza-Michael-type addition reaction catalysed by a supported ionic liquid phase incorporating an anionic heteropoly acid
Ghasemi, Mohammad Hadi,Kowsari, Elaheh,Shafiee, Abbas
, p. 1150 - 1153 (2016/03/09)
In this work, we have obtained substituted amines under mild conditions in good yields using the Aza-Michael-type addition of various amines to vinyl compounds catalysed by a supported ionic liquid incorporating an anionic heteropoly acid. Different catalysts, including Lewis acids, Br?nsted acids and heteropoly acids were investigated in which heteropoly acids having dual Br?nsted and Lewis acid characteristics were excellent catalysts. The ionic liquid incorporating a polytungstate anion supported on magnetic diatomaceous earth as a magnetically separable heterogeneous catalyst offered the best results in terms of yield. The solid nanocatalyst was easily removed with a magnet.
Anti-markovnikov hydroamination of aromatic alkenes with secondary amines catalyzed by easily accessible yttrium complexes
Germain, Stephane,Schulz, Emmanuelle,Hannedouche, Jerome
, p. 2065 - 2073 (2014/08/05)
Binaphthylamido alkyl yttrium complexes have been proven to promote the anti-Markovnikov addition between various styrene derivatives and secondary amines efficiently. Although the reaction has to be performed at high temperature, it is realized advantage
7-Azabicyclo[2.2.1]heptane as a scaffold for the development of selective sigma-2 (σ2) receptor ligands
Banister, Samuel D.,Rendina, Louis M.,Kassiou, Michael
supporting information; experimental part, p. 4059 - 4063 (2012/07/03)
A series of N-substituted 7-azabicyclo[2.2.1]heptanes (12-17 and 22-25) and similarly substituted pyrrolidines (32-36 and 41-44) were synthesized as sterically-reduced, achiral analogs of adamantane- and trishomocubane-derived σ ligands. In vitro competition binding assays against σ receptors revealed that arylalkyl N-substituents conferred selectivity for the σ2 subtype, while alicyclic or polycarbocyclic substituents imparted high affinity for both subtypes. The σ2 binding and subtype selectivities of N-arylalkyl-7-azanorbornanes was generally greater than the analogously-substituted pyrrolidines, indicating that steric bulk and conformational restriction around the nitrogen atom are likely important for subtype discrimination.
In vitro SAR of pyrrolidine-containing histamine H3 receptor antagonists: Trends across multiple chemical series
Nersesian, Diana L.,Black, Lawrence A.,Miller, Thomas R.,Vortherms, Timothy A.,Esbenshade, Timothy A.,Hancock, Arthur A.,Cowart, Marlon D.
, p. 355 - 359 (2008/04/03)
Structure-activity relationships (SAR) were analyzed within a library of diverse yet simple compounds prepared as histamine H3 antagonists. The libraries were constructed with a variety of low molecular weight pyrrolidines, selected from (R)-2-methylpyrrolidine, (S)-2-methylpyrrolidine, and pyrrolidine.
Anti-Markonikov reactions, 6. Rhodium-catalyzed amination of vinylpyridines: Hydroamination versus oxidative amination
Beller, Matthias,Trauthwein, Harald,Eichberger, Martin,Breindl, Claudia,Mueller, Thomas E.
, p. 1121 - 1132 (2007/10/03)
Cationic rhodium complexes catalyze the amination of 2- and 4- vinylpyridine with secondary amines. Depending on the substrate and the reaction conditions either oxidative amination to yield the corresponding enamines 1a-8a or hydroamination to give 2-aminoethylpyridines 1b-8b occurs. In all cases products with anti-Markovnikov regioselectivity are obtained. For mechanistic studies novel cationic complexes of rhodium(I)-containing cyclooctadiene and vinylpyridine 12 as well as complexes containing cyclooctadiene, vinylpyridine, and morpholine 13 were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis.
