574744-39-1Relevant academic research and scientific papers
Co-Catalyzed Synthesis of Primary Amines via Reductive Amination employing Hydrogen under very mild Conditions
Elfinger, Matthias,Sch?nauer, Timon,Thom?, Sabrina L. J.,St?glich, Robert,Drechsler, Markus,Zobel, Mirijam,Senker, Jürgen,Kempe, Rhett
, p. 2360 - 2366 (2021/05/03)
Nanostructured and reusable 3d-metal catalysts that operate with high activity and selectivity in important chemical reactions are highly desirable. Here, a cobalt catalyst was developed for the synthesis of primary amines via reductive amination employing hydrogen as the reducing agent and easy-to-handle ammonia, dissolved in water, as the nitrogen source. The catalyst operates under very mild conditions (1.5 mol% catalyst loading, 50 °C and 10 bar H2 pressure) and outperforms commercially available noble metal catalysts (Pd, Pt, Ru, Rh, Ir). A broad scope and a very good functional group tolerance were observed. The key for the high activity seemed to be the used support: an N-doped amorphous carbon material with small and turbostratically disordered graphitic domains, which is microporous with a bimodal size distribution and with basic NH functionalities in the pores.
Chiral Bronsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH-Imine Hydrochloride Salts
Wakchaure, Vijay N.,Obradors, Carla,List, Benjamin
supporting information, p. 1707 - 1712 (2020/08/28)
While imines are frequently used substrates in asymmetric Bronsted acid catalysis, their corresponding salts are generally considered unsuitable reaction partners. Such processes are challenging because they require the successful competition of a catalytic amount of a chiral anion with a stoichiometric amount of an achiral one. We now show that enantiopure disulfonimides enable the asymmetric reduction of N-H imine hydrochloride salts using Hantzsch esters as hydrogen source. Our scalable reaction delivers crystalline primary amine salts in great efficiency and enantioselectivity and the discovery suggests potential of this approach in other Bronsted acid catalyzed transformations of achiral iminium salts. Kinetic studies and acidity data suggest a bifunctional catalytic activation mode.
Synthesis method of primary amine hydrochloride
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Paragraph 0064-0067, (2019/03/09)
The invention discloses a synthesis method of primary amine hydrochloride. According to the synthesis method, in the presence of a gold complex, water and alkyne carry out catalytic hydrolysis to generate ketones, and then ketones and ammonium formate are catalyzed by a rhodium complex to generate primary amine. Compared with a conventional primary amine synthesis method, the synthesis method hasthe advantages that no alkali is added during the reaction process, no side product is generated, the atomic economy is good, the reaction conditions are mild, and the synthesis method has a wide prospect.
Reusable Nickel Nanoparticles-Catalyzed Reductive Amination for Selective Synthesis of Primary Amines
Murugesan, Kathiravan,Beller, Matthias,Jagadeesh, Rajenahally V.
supporting information, p. 5064 - 5068 (2019/03/19)
The preparation of nickel nanoparticles as efficient reductive amination catalysts by pyrolysis of in situ generated Ni-tartaric acid complex on silica is presented. The resulting stable and reusable Ni-nanocatalyst enables the synthesis of functionalized and structurally diverse primary benzylic, heterocyclic and aliphatic amines starting from inexpensive and readily available carbonyl compounds and ammonia in presence of molecular hydrogen. Applying this Ni-based amination protocol, -NH2 moiety can be introduced in structurally complex compounds, for example, steroid derivatives and pharmaceuticals.
Synthesis of α-Substituted Primary Benzylamines through Copper-Catalyzed Cross-Dehydrogenative Coupling
Kramer, S?ren
supporting information, p. 65 - 69 (2019/01/04)
A copper-catalyzed route to α-substituted, primary benzylamines by C-H functionalization of alkylarenes is described. The method directly affords the amine hydrochloride salt. Catalyst loadings down to 0.1 mol % in combination with scalability, insensitivity to air and moisture, and no need for column chromatography makes the procedure highly practical. The facile synthesis of the racemate of a blockbuster drug highlights the relevance for the development of pharmaceuticals. Preliminary mechanistic data are also included.
Donor Amine Salt-Based Continuous in situ-Product Crystallization in Amine Transaminase-Catalyzed Reactions
Hülsewede, Dennis,Dohm, Jan-Niklas,von Langermann, Jan
supporting information, p. 2727 - 2733 (2019/05/22)
The unfavorable reaction equilibrium of transaminase-catalyzed reactions is a major challenge for the efficient biocatalytic synthesis of chiral amines. In this study the synthetic utilization of a salt-based, continuous in situ-product crystallization is
APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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Paragraph 0138, (2018/10/27)
PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
Asymmetric Reduction of tert-Butanesulfinyl Ketimines by N-Heterocyclic Carbene Boranes
Liu, Tao,Chen, Ling-Yan,Sun, Zhihua
, p. 11441 - 11446 (2015/12/01)
N-heterocyclic carbene borane (NHC-borane) based on a triazole core is demonstrated for the first time to be efficient for reduction of a variety of tert-butanesulfinyl ketimines. Up to 95% yield and up to >99% diastereomeric excess were achieved. NHC-borane exhibited excellent activities that are more efficient than or comparable to commonly used reductive reagents such as NaBH4, NaBH3CN, l-selectride, Ru catalyst, or BH3-THF.
Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea
Zhao, Qingyang,Wen, Jialin,Tan, Renchang,Huang, Kexuan,Metola, Pedro,Wang, Rui,Anslyn, Eric V.,Zhang, Xumu
supporting information, p. 8467 - 8470 (2014/08/18)
Asymmetric hydrogenation of unprotected NH imines catalyzed by rhodium/bis(phosphine)-thiourea provided chiral amines with up to 97% yield and 95% ee. 1HNMR studies, coupled with control experiments, implied that catalytic chloride-bound intermediates were involved in the mechanism through a dual hydrogen-bonding interaction. Deuteration experiments proved that the hydrogenation proceeded through a pathway consistent with an imine.
N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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Paragraph 0231, (2013/03/26)
The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
