499775-83-6Relevant academic research and scientific papers
A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water
Wei, Chunmei,Li, Chao-Jun
, p. 9584 - 9585 (2003)
A highly efficient three-component-coupling of aldehyde, alkyne, and amine (A3 Coupling) catalyzed by gold via C-H activation was developed in water. The reaction is general, and nearly quantitative yields of the corresponding propargylamines were obtained in most cases. Both aromatic and aliphatic aldehydes and amines can be used for the reaction. No additional cocatalyst or activator is required. A mechanistic rationale for the reaction has been proposed. Copyright
Ag2CO3-catalyzed efficient synthesis of internal or terminal propargylicamines and chalcones via A3-coupling under solvent-free condition
Li, Ningbo,Xu, Shitang,Wang, Xueyan,Xu, Li,Qiao, Jie,Liang, Zhiwu,Xu, Xinhua
, p. 3993 - 3997 (2021/05/31)
Several simple, fast and practical protocols have been developed to synthesize internal or terminal propargylamines and chalcones via A3-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag2CO3 under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated. Furthermore, plausible mechanisms for the synthesis of different products have been proposed.
1D Fe3O4&at;CuSiO3 composites catalyzed decarboxylative A3-coupling for propargylamine synthesis
Cao, Tiantian,Feng, Huangdi,Li, Huiqiong,Miao, Teng,Wang, Fang,Zhang, Min
, p. 1558 - 1563 (2020/07/30)
Highly active and stable magnetic copper catalysts were successfully achieved by magnetic induced St?ber method and subsequent hydrothermal reaction with copper ions in alkaline condition. The high content of Cu2+ as well as the unique structures of hierarchical copper silicate in the as-prepared catalysts endowed their outstanding catalytic performance. Efficient decarboxylative A3-coupling of α-keto acid, amine and alkyne was realized with the low Fe3O4&at;CuSiO3 loading. A range of propargylamines were produced in good to excellent yields under solvent-free condition. Moreover, the catalyst can be easily separated from the final organic product with an external magnet. Also, this kind of catalyst could be recycled up to six times while maintaining its activity.
Silver chloride supported on Vitamin B1 -Organometallic magnetic catalyst: synthesis, density functional theory study and application in A3-coupling reactions
Esfandiary, Naghmeh,Pazoki, Farzane,Nakisa, Athar,Azizi, Kobra,Radfar, Iman,Heydari, Akbar
, (2020/06/03)
A highly efficient Fe3O4@VitB1–Ag(I) magnetic catalyst has been obtained using surface modification of Fe3O4. To this end, silver chloride was immobilized on Fe3O4 nanoparticles
Expeditious and highly efficient synthesis of propargylamines using a Pd-Cu nanowires catalyst under solvent-free conditions
Yi, Rongnan,Wang, Zheng-Jun,Liang, Zhiwu,Xiao, Min,Xu, Xinhua,Li, Ningbo
, (2019/04/08)
A heterogeneous Pd-Cu NWs-catalyzed expeditious and solvent-free synthesis of propargylamines via A3-coupling of aldehydes, alkynes, and amines has been proposed. A wide range of aldehydes, alkynes and amine substrates undergo A3-coupling to produce propargylamines in good to excellent yields with good functional tolerance, such as that towards alkoxy, hydroxy, C-X (X?=?F, Cl, Br) as well as amide and C=C bonds. Furthermore, the catalyst could be recovered easily and reused for at least 5?cycles without showing significant loss of catalytic activity.
Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines
Salvant, Justin M.,Edwards, Anne V.,Kurek, Daniel Z.,Looper, Ryan E.
, p. 6958 - 6967 (2017/07/15)
A regioselective base-mediated cyclization of mono-N-acylpropargylguanidines is reported. A related Ag(I)-catalyzed hydroamination strategy was recently employed to yield N3-Cbz-protected ene-guanidines, which found utility in the synthesis of
Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(i) bis-metal sequential catalysis
Huang, Pei-Qiang,Ou, Wei,Han, Feng
supporting information, p. 11967 - 11970 (2016/10/09)
We report herein a convenient and versatile method for the direct reductive alkynylation of tertiary amides to give propargylic amines through sequential Ir-catalysed hydrosilylation-Cu(i)-catalysed alkynylation. The reactions proceed chemoselectively at the amide group in the presence of several sensitive functional groups including the very reactive aldehyde group on either the amide or the alkyne coupling partner. The method is general for tert-amides with or without α-hydrogen.
COMPOSITIONS AND METHODS COMPRISING 2-(ACYLAMINO)IMIDAZOLES
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Paragraph 0293, (2015/11/10)
The present invention presents 2-(acylamino)imidazoles with therapeutic activity, including selective activity against cancer cells, and compositions comprising them. Methods of using and preparing the 2-(acylamino)imidazoles are also presented.
Mannich reactions of alkynes: Mechanistic insights and the role of sub-stoichiometric amounts of alkynylcopper(I) compounds in the catalytic cycle
Buckley, Benjamin R.,Khan, Amna N.,Heaney, Harry
supporting information; experimental part, p. 3855 - 3858 (2012/05/20)
Yellow polymeric alkynylcopper(I) compounds observed in the three-component Mannich reactions of alkynes, secondary amines and aldehydes are shown to be pre-catalysts that give rise to catalytic copper(I) alkyne complexes by interaction with secondary amines (see scheme). Interaction of these complexes with iminium ions (formed from aldehydes or their equivalents, including CH 2Cl2), results in the formation of Mannich bases in high yields. Copyright
Microwave-assisted decarboxylative three-component coupling of a 2-oxoacetic acid, an amine, and an alkyne
Feng, Huangdi,Ermolat'Ev, Denis S.,Song, Gonghua,Van Der Eycken, Erik V
supporting information; experimental part, p. 7608 - 7613 (2011/11/12)
A novel and efficient microwave-assisted decarboxylative three-component coupling of a 2-oxoacetic acid, an amine, and an alkyne (OA2- coulpling) has been developed. This new multicomponent coupling constitutes an efficient approach for the syn
