25611-78-3Relevant academic research and scientific papers
Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones
Polishchuk, Iuliia,Sklyaruk, Jan,Lebedev, Yury,Rueping, Magnus
supporting information, p. 5919 - 5922 (2021/03/08)
Half-sandwich iridium complexes bearing bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α-position.
Pyrimidopteridine-Catalyzed Hydroamination of Stilbenes with Primary Amines: A Dual Photoredox and Hydrogen Atom Transfer Catalyst
Taeufer, Tobias,Hauptmann, Richy,El-Hage, Firas,Mayer, Thea S.,Jiao, Haijun,Rabeah, Jabor,Pospech, Jola
, p. 4862 - 4869 (2021/05/04)
The applicability of a heteroaromatic photoredox catalyst in an additive-free photo-mediated hydroamination of stilbenes is described. Initiated by the excitation of a highly potent organic pyrimidopteridine photoredox catalyst (E?[PrPPT?/PrPPT·-] = +2.10 V vs SCE in MeCN), the photo-mediated hydroamination of stilbenes was enabled using unprotected, primary aliphatic, allylic, benzylic amines for the synthesis of various α-phenyl phenethylamine derivatives. Notably, the stereogenic center of α-chiral amines was fully preserved. Both starting materials serve as competent quenching partners. Fluorescence- and competitive fluorescence-quenching experiments as well as electron paramagnetic resonance spectroscopic analysis and density functional theory calculations allowed a plausible reaction mechanism to be deduced.
Direct Access to Primary Amines from Alkenes by Selective Metal-Free Hydroamination
Du, Yi-Dan,Chen, Bi-Hong,Shu, Wei
supporting information, p. 9875 - 9880 (2021/03/29)
Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal-free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for the first time, allowing for efficient conversion of terminal and internal alkenes into linear, α-branched, and α-tertiary primary amines under mild conditions. This method provides a straightforward and powerful approach to a wide spectrum of advanced, highly functionalized primary amines which are of particular interest in pharmaceutical chemistry and other areas.
Ultra-small cobalt nanoparticles from molecularly-defined Co-salen complexes for catalytic synthesis of amines
Beller, Matthias,Chandrashekhar, Vishwas G.,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kalevaru, Narayana V.,Kamer, Paul C. J.,Senthamarai, Thirusangumurugan,Zbo?il, Radek
, p. 2973 - 2981 (2020/03/27)
We report the synthesis of in situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt-salen complexes such as cobalt(ii)-N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2-4 nm) cobalt-nanoparticles embedded in a carbon-nitrogen framework. The resulting materials constitute stable, reusable and magnetically separable catalysts, which enable the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds and ammonia. The isolated nanoparticles also represent excellent catalysts for the synthesis of primary, secondary as well as tertiary amines including biologically relevant N-methyl amines.
Alkaline-metal-catalyzed one-pot aminobenzylation of aldehydes with toluenes
Liu, Guoqing,Walsh, Patrick J.,Mao, Jianyou
supporting information, p. 8514 - 8518 (2019/10/11)
A novel and easily accessible MN(SiMe3)2 (M = Li or Na)/Cs2CO3 co-catalyzed benzylation of in situ generated N-(trimethylsilyl) aldimines with toluene derivatives has been successfully developed. The catalyst exhibits high chemoselectivity for deprotonation of toluenes at the benzylic position. The utility of this system is exemplified by the one-pot synthesis of a diverse array of bioactive 1,2-diarylethylamines with excellent efficiency and broad functional group tolerance.
Hydrogen bond directed aerobic oxidation of amines via photoredox catalysis
Wang, Hongyu,Man, Yunquan,Wang, Kaiye,Wan, Xiuyan,Tong, Lili,Li, Na,Tang, Bo
supporting information, p. 10989 - 10992 (2018/10/08)
An application of H-bonding interactions for directing the α-C-H oxidation of amines to amides and amino-ketones catalyzed by an organic photocatalyst is reported. The high efficiency of this method is demonstrated by the aerobic oxidation of pyrrolidines, diarylamines and benzylamines bearing urea groups with high yields and a wide substrate scope.
Catalytic Direct-Type Addition Reactions of Alkylarenes with Imines and Alkenes
Yamashita, Yasuhiro,Suzuki, Hirotsugu,Sato, Io,Hirata, Tsubasa,Kobayashi, Shū
supporting information, p. 6896 - 6900 (2018/05/14)
Catalytic addition reactions of very weakly acidic nonactivated alkylarenes such as toluene and its derivatives were developed by using a strongly basic mixed catalyst system under mild reaction conditions. The addition reactions with imines and alkenes proceeded smoothly under proton-transfer conditions to afford the desired products in good to high yields, and high levels of regio- and stereoselectivity were achieved. It was also revealed that the asymmetric addition reaction of an alkylarene was possible.
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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, (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
An efficient synthesis of substituted isoxazolopyrroloisoquinolines via diastereoselective N-acyliminium ion cyclization
Ledovskaya, Maria S.,Molchanov, Alexander P.,Boitsov, Vitaly M.,Kostikov, Rafael R.,Stepakov, Alexander V.
, p. 1952 - 1958 (2015/04/14)
A simple and efficient strategy was developed for the synthesis of fused pyrrolo[2,1-a]isoquinoline ring systems. The 5- and 6-substituted isoxazolopyrroloisoquinolines were readily prepared via diastereoselective N-acyliminium ion cyclization of 5-(1-R(or 2-R)-substituted-2-phenylethyl)-6-hydroxytetrahydro-4H-pyrrolo[3,4-d]isoxazol-4-ones derived from the corresponding bicyclic dihydroisoxazoles.
Rapid, one-pot synthesis of α,α-disubstituted primary amines by the addition of Grignard reagents to nitriles under microwave heating conditions
Gregg, Brian T.,Golden, Kathryn C.,Quinn, John F.,Wang, Hong-Jun,Zhang, Wei,Wang, Ruifang,Wekesa, Francis,Tymoshenko, Dmytro O.
experimental part, p. 3978 - 3981 (2009/10/04)
A series of α,α-disubstituted amines have been prepared in a simple and efficient one-pot procedure by the addition of Grignard reagents to a series of aliphatic, aromatic, and heteroaromatic nitriles. Key to this reported procedure is the unprecedented addition of the Grignard reagent to the nitrile under heating by microwave irradiation which both significantly improves reaction yields and reduces reaction times. In general, the Grignard addition reaction is complete within 5-10 min at 100 °C followed by rapid reduction with sodium borohydride to give the target amines.
