434935-92-9Relevant academic research and scientific papers
Highly efficient Grignard-type imine additions via C-H activation in water and under solvent-free conditions
Li, Chao-Jun,Wei, Chunmei
, p. 268 - 269 (2002)
A highly effective Cu-Ru catalyzed addition of terminal alkynes to imines via C-H activation has been achieved in water or under solvent-free conditions.
Tetrasubstituted imidazolium salts as potent antiparasitic agents against African and American trypanosomiases
Ghashghaei, Ouldouz,Kielland, Nicola,Revés, Marc,Taylor, Martin C.,Kelly, John M.,Pietro, Ornella Di,oz-Torrero, Diego Mu,Pérez, Belén,Lavilla, Rodolfo
supporting information, (2018/01/26)
Imidazolium salts are privileged compounds in organic chemistry, and have valuable biological properties. Recent studies show that symmetric imidazolium salts with bulky moieties can display antiparasitic activity against T. cruzi. After developing a faci
Modular Access to Tetrasubstituted Imidazolium Salts through Acid-Catalyzed Addition of Isocyanides to Propargylamines
Ghashghaei, Ouldouz,Revés, Marc,Kielland, Nicola,Lavilla, Rodolfo
supporting information, p. 4383 - 4388 (2015/07/27)
Propargylamines, prepared through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. The key step of the mechanism involves the generation of an amidine intermediate, from the isocyanide insertion into the N-H bond of the propargylamine, which in situ evolves by cyclization upon the alkyne moiety. The scope of the process is analyzed and only shows restrictions for aliphatic amines, whereas it is quite general regarding the aldehyde, alkyne and isocyanide inputs. The protocol allows the preparation of a wide array of adducts, tandem one-pot processes being also feasible. Mechanistic studies using selected substrates have been used to determine the profile of the reaction and some substitution and functional group limitations. Some post-synthetic transformations of the imidazolium salts have been performed as well. Propargylamines, synthesized through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. Tandem one-pot protocols allow direct access to these adducts from the commercially available inputs.
A bimetallic iridium(ii) catalyst: [{Ir(IDipp)(H)}2][BF4]2 (IDipp = 1,3-bis(2,6-diisopropylphenylimidazol-2-ylidene))
Rubio-Pérez, Laura,Iglesias, Manuel,Munárriz, Julen,Polo, Victor,Sanz Miguel, Pablo J.,Pérez-Torrente, Jesús J.,Oro, Luis A.
supporting information, p. 9860 - 9863 (2015/06/16)
A new Ir(ii) complex [{Ir(μ-κCNHC,η6Dipp-IDipp)(H)}2][BF4]2 has been prepared and fully characterised. This complex acts as a catalyst for the hydroalkynylation of imines according to an un
Tuning the reactivity of isocyano group: Synthesis of imidazoles and imidazoliums from propargylamines and isonitriles in the presence of multiple catalysts
Tong, Shuo,Wang, Qian,Wang, Mei-Xiang,Zhu, Jieping
supporting information, p. 1293 - 1297 (2015/02/19)
The reaction of propargyl amines with tert-butylisonitrile in the presence of a catalytic amount of both Yb(OTf)3 and AgOTf afforded imidazoles, whereas the same reaction with primary and secondary alkylisonitriles, as well as arylisonitriles, in the presence of three metal salts [Yb(OTf)3/AgOTf/KOTf] resulted in the 1,3,4,5-tetrasubstituted imidazoliums in excellent yields. Both chiral amines and chiral isonitriles can be used to provide corresponding chiral heterocycles without racemization. In this multiple catalytic system, Yb(OTf)3 catalyzed the insertion of isonitriles to the N-H bond of amines, AgOTf catalyzed the 5-exo-dig cyclization of the resulting amidine nitrogen to the tethered triple bond, and KOTf promoted the salt metathesis, thus providing at the same time the counterion to the imidazolium. Against common knowledge, the isocyano group acted in these reactions as a polarized triple bond instead of conventional carbene-like function.
A novel efficient method for synthesis of propargylamines via three-component coupling of aryl azide, aldehyde, and alkyne promoted by iron-iodine-copper(I) bromide
Zhang, Kui,Huang, You,Chen, Ruyu
supporting information; experimental part, p. 5463 - 5465 (2010/10/20)
A novel, efficient method has been developed for the synthesis of propargylamines through a three-component coupling of aryl azides, aldehydes, and alkynes in the presence of iron-iodine-copper(I) bromide as catalyst. This method is the first example for directly using aryl azides as an amino component in a three-component coupling reaction. Some of the major advantages of this protocol are: good yields, the involvement of a less-expensive and non-toxic catalyst, mild reaction conditions, and a wide range of substrates.
Sequential catalytic process: synthesis of quinoline derivatives by AuCl3/CuBr-catalyzed three-component reaction of aldehydes, amines, and alkynes
Xiao, Fengping,Chen, Yulin,Liu, Yu,Wang, Jianbo
, p. 2755 - 2761 (2008/09/19)
A sequential catalytic process has been developed based on gold-catalyzed nucleophilic addition of terminal alkynes to imines, and gold-catalyzed intramolecular reaction of aromatic ring to alkynes. This one-pot reaction of aldehydes, amines, and alkynes gives quinoline derivatives in good yields.
