35223-73-5Relevant academic research and scientific papers
Molecular design of organic superbases, azacalix[3](2,6)pyridines: Catalysts for 1,2-and 1,4-additions
Uchida, Natsuko,Kuwabara, Junpei,Taketoshi, Ayako,Kanbara, Takaki
, p. 10631 - 10637 (2013/02/22)
The molecular design, characteristics, and catalytic activity of macrocyclic amino compounds, azacalix[3](2,6)pyridine derivatives, were studied. The introduction of an electron-donating group on the pyridine moiety and bridging amino phenyl group enabled the enhancement of the basicity of azacalix[3](2,6)pyridine up to pKBH+ = 29.5 in CD3CN. These derivatives were shown to be efficient catalysts for 1,4-addition reactions of nitroalkanes or primary alcohols to α,β-unsaturated carbonyl compounds and 1,2-addition reactions of nitroalkanes to aromatic aldehydes.
Synthesis, characterization, and catalytic reactivity of a highly basic macrotricyclic aminopyridine
Uchida, Natsuko,Taketoshi, Ayako,Kuwabara, Junpei,Yamamoto, Toshihide,Inoue, Yoshiaki,Watanabe, Yu,Kanbara, Takaki
scheme or table, p. 5242 - 5245 (2011/02/24)
The synthesis methods, physicochemical and structural characteristics, and catalytic reactivity of new macrocyclic proton chelators, N,N′,N″- tris(p-tolyl)azacalix[3](2,6)(4-pyrrolidinopyridine) and N,N′,N″- tris(p-tolyl)azacalix[3](2,6)(4-piperidinopyridine), are studied. The introduction of pyrrolidino and piperidino groups into the pyridine unit enables the enhancement of the synergistic proton affinity of the cavity of the macrotricycle giving a high basicity (pKBH+ = 28.1 and 27.1 in CD3CN), resulting in a catalytic activity for the Michael addition of nitromethane with α,β-unsaturated carbonyl compounds.
SUBSTITUTED IMIDAZO RING SYSTEMS AND METHODS
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Page/Page column 104, (2008/06/13)
Imidazo ring systems substituted at the 1-position, pharmaceutical compositions containing the compounds, intermediates, methods of making the compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in anim
P(RNCH2CH2)3N: Efficient 1,4-addition catalysts
Kisanga, Philip B.,Ilankumaran, Palanichamy,Fetterly, Brandon M.,Verkade, John G.
, p. 3555 - 3560 (2007/10/03)
The 1,4-addition of primary alcohols, higher nitroalkanes, and a Schiff's base of an α-amino ester to α,β-unsaturated substrates produces the corresponding products in moderate to excellent yields when carried out at -63 to 70°C in the presence of catalytic amounts of the nonionic strong bases P(RNCH2CH2)3N (R = Me, i-Pr, i-Bu) in isobutyronitrile. Diastereoselectivity for the anti form of the product is high in the case of the Schiff's base in the absence of lithium ion. These catalysts are easily removed from the product by either column filtration through silica gel or via aqueous workup.
Origin of "Hetero Effect" on Nitrogen Inversion. Comparison of Hydroxylamines and Aminoxide Anions
Perrin, Charles L.,Thoburn, John D.,Elsheimer, Seth
, p. 7034 - 7038 (2007/10/02)
Rate constants for nitrogen inversion in N-benzyl-N-methylhydroxylamine, N,N-diethylhydroxylamine, 1-hydroxy-2,2,4,4-tetramethylpyrrolidine, their conjugate bases, and their O-acetyl derivatives in dimethylformamide-d7 were determined based on the 1H NMR
Synthesis and Chemistry of Azolenines. Part 16. Preparation of both 3H- and 2H-Pyrroles from 2,2-Disubstituted 1,4-Diketones via the Paal-Knorr Reaction, and Isolation of Intermediate 2-Hydroxy-3,4-dihydro-2H-pyrroles
Lui, Kon-Hung,Sammes, Michael P.
, p. 457 - 468 (2007/10/02)
Treatment of 2,2-disubstituted 1,4-diketones (1) with liquid ammonia gives high yields of isolable isomeric 2-hydroxy-3,4-dihydro-2H-pyrroles (10) and (11), many of which may be dehydrated to 3H-pyrroles (2) together, in certain cases, with isomeric methylene-pyrrolines (14) and (15).When heated in acetic acid with ammonium acetate, the diketones (1) yield 2H-pyrroles (18), sometimes in admixture with 3H-pyrroles (2) from which they are formed by rearrangement.The diketones (1), including some novel examples, are prepared from nitro-ketones (6) by the Nef reaction, as well as other methods.
