28709-71-9Relevant academic research and scientific papers
Anchored Palladium Complex-Generated Clusters on Zirconia: Efficiency in Reductive N-Alkylation of Amines with Carbonyl Compounds under Hydrogen Atmosphere
Zhang, Zhenzhong,Ikeda, Takuya,Murayama, Haruno,Honma, Tetsuo,Tokunaga, Makoto,Motoyama, Yukihiro
, (2022/03/15)
Carbon-nitrogen bond formation is an important method on both laboratory and industrial scales because it realizes the production of valuable pharmaceuticals, agrochemicals, and fine chemicals. Direct reductive N-alkylation of amines with carbonyl compounds via intermediary imine compounds, especially under catalytic hydrogenation conditions, is one of the most convenient, economical, and environmentally friendly methods for this process. Here we report a novel palladium species on zirconia having specific activity towards hydrogenation of imines but other carbonyl groups remaining intact. The present catalytic property offers a practical synthetic method of functionalized secondary amines by reductive N-alkylation under mild conditions with high atom-efficiency. Mechanistic studies revealed that the catalytically active species is the palladium cluster, which is generated in situ from molecular palladium complexes on the support by exposure to atmospheric hydrogen. These fundamental findings are expected to progress in developing novel cluster catalysts for chemical processes directed towards a sustainable society.
Enantioselective synthesis of α-secondary and α-tertiary piperazin-2- Ones and piperazines by catalytic asymmetric allylic alkylation
Korch, Katerina M.,Eidamshaus, Christian,Behenna, Douglas C.,Stoltz, Brian M.,Nam, Sangkil,Horne, David
supporting information, p. 179 - 183 (2015/02/05)
The asymmetric palladium-catalyzed decarboxylative allylic alkylation of differentially N-protected piperazin-2- ones allows the synthesis of a variety of highly enantioenriched tertiary piperazine-2-ones. Deprotection and reduction affords the corresponding tertiary piperazines, which can be employed for the synthesis of medicinally important analogues. The introduction of these chiral tertiary piperazines resulted in imatinib analogues which exhibited comparable antiproliferative activity to that of their corresponding imatinib counterparts.
Base-promoted c→n acyl rearrangement: An unconventional approach to α-amino acid derivatives
Ugarriza, Iratxe,Uria, Uxue,Carrillo, Luisa,Vicario, Jose L.,Reyes, Efraim
supporting information, p. 11650 - 11654 (2014/10/15)
We have discovered that N-alkyl aminomalonates undergo a fast and selective intramolecular C→N acyl rearrangement reaction in the presence of a strong base, leading to N-protected glycinates in excellent yield. Moreover, the fact that the reaction proceeds through a nucleophilic enolate intermediate has been used for implementing a tandem rearrangement/alkylation sequence that has been applied to the preparation of synthetically relevant nonproteinogenic tertiary and quaternary N-alkyl α-amino acids in a very simple and reliable way.
Memory of chirality (MOC) concept in imino-aldol reaction: Enantioselective synthesis of α,β-diamino esters and aziridines
Ghorai, Manas K.,Ghosh, Koena,Yadav,Nanaji,Halder, Sandipan,Sayyad, Masthanvali
, p. 2311 - 2326 (2013/04/24)
A simple strategy for the synthesis of chiral α,β-diamino- and α-amino,β-hydroxy ester derivatives in high yields with moderate to high ee has been developed via asymmetric imino-aldol and aldol reactions, respectively, starting from protected aminoesters employing memory of chirality concept for chiral induction. This strategy has been extended for the enantioselective synthesis of aziridines (ee up to 92%). The absolute configuration of the imino-aldol adducts has been determined. The stereochemical outcome of the products has been explained by a suitable mechanism and supported by computational studies.
Ammonolysis of morpholine-2,5-diones: Participation of the primary amide group. Part 2
Arcelli, Antonio,Bongini, Alessandro,Porzi, Gianni,Rinaldi, Samuele
, p. 132 - 141 (2012/05/04)
The ammonolysis of three morpholine-2,5-dione derivatives was investigated and the mechanism ascertained by kinetic studies and theoretical calculations. The kinetics, followed by high-performance liquid chromatography analysis, evidenced the presence of two intermediates, which were isolated and characterized. The ammonolysis occurs with a complex mechanism involving two consecutive reactions followed by two parallel ones. The second step of the whole reaction involves an anchimeric assistance of the primary amide group. The pseudo-first-order rate constants were calculated by appropriate equations, which describe the single steps of the process. Computational density functional theory investigations of vicinal primary amide group participation were performed using a model compound, and the transition states were generated. The theoretical calculations evidenced the essential role exerted by ammonia, which acts as a proton transfer.
A Straightforward Three-Component Synthesis of α-Amino Esters Containing a Phenylalanine or a Phenylglycine Scaffold
Haurena, Caroline,Le Gall, Erwan,Sengmany, Stephane,Martens, Thierry,Troupel, Michel
supporting information; experimental part, p. 2645 - 2650 (2010/07/02)
A range of α-amino esters has been synthesized in good to high yields using a straightforward three-component reaction among preformed or in situ generated aromatic or benzylic organozinc reagents, primary or secondary amines, and ethyl glyoxylate. The procedure, which is characterized by its simplicity, allows the concise synthesis of esters bearing a phenylglycine or a phenylalanine scaffold.
Enantioselective synthesis of α,β-diamino ester derivatives: memory of chirality in imino-aldol reactions
Ghorai, Manas K.,Ghosh, Koena,Yadav
scheme or table, p. 476 - 479 (2009/05/07)
A simple strategy for the synthesis of chiral α,β-diamino ester derivatives in good yields and ee (up to 92%) utilizing the 'memory of chirality' concept is reported. This methodology has been extended for the enantioselective synthesis of substituted azi
Analogs of tetramic acid
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Page/Page column 5, (2009/04/24)
Tetramic acid analogues of Formula I and Formula II have antibacterial activity, primarily against gram-positive bacteria, and are iron chelators.
N-substituted 3-acetyltetramic acid derivatives as antibacterial agents
Yendapally, Raghunandan,Hurdle, Julian G.,Carson, Elizabeth I.,Lee, Robin B.,Lee, Richard E.
, p. 1487 - 1491 (2008/12/21)
In order to expand the structure-activity relationship of tetramic acid molecules with structural similarity to the antibiotic reutericyclin, 22 compounds were synthesized and tested against a panel of clinically relevant bacteria. Key structural changes
