606123-82-4Relevant articles and documents
Carbamoylation of Azomethine Imines via Visible-Light Photoredox Catalysis
Correia, José Tiago M.,Matsuo, Bianca T.,Oliveira, Pedro H. R.,Paix?o, Márcio W.
supporting information, p. 6775 - 6779 (2021/09/13)
A versatile and robust photocatalytic methodology to install the amide functional group into azomethine imine ions is described. This protocol is distinguished by its broad scope and mild reaction conditions, which are well suited for the preparation of s
Visible-Light-Mediated α-Amino Alkylation of Azomethine Imines: An Approach to N-(β-Aminoalkyl)pyrazolidinones
Matsuo, Bianca T.,Correia, José Tiago M.,Paix?o, Márcio W.
supporting information, p. 7891 - 7896 (2020/11/02)
Herein, a mild and robust photocatalytic protocol for the combination of amino and pyrazolidinone functionalities through a radical α-amino alkylation of azomethine iminium ions is demonstrated. This method presents a high functional group tolerance provi
[3 + 2]-Cycloadditions of Azomethine Imines and Ynolates
Winterton, Sarah E.,Ready, Joseph M.
supporting information, p. 2608 - 2611 (2016/06/15)
A novel [3 + 2]-cycloaddition between azomethine imines and lithium ynolates is described to synthesize bicyclic pyrazolidinones. These bicyclic pyrazolidinones are versatile intermediates to form β-amino acids and monocyclic pyrazolidinones. High diaster
Chiral Iron(II) NPPN Complexes: Synthesis and Application in the Asymmetric Strecker Reaction of Azomethine Imines
Huber, Raffael,Bigler, Raphael,Mezzetti, Antonio
supporting information, p. 3374 - 3384 (2016/01/15)
The open-chain NPPN ligand (1S,1′S)-1,1′-((ethane-1,2-diylbis(phenylphosphanediyl))bis(2,1-phenylene))bis(N-cyclohexylmethanimine) (1) was prepared by condensation of cyclohexylamine with enantiomerically pure (1S,1′S)-2,2′-(ethane-1,2-diylbis(phenylphosphanediyl))dibenzaldehyde ((S,S)-6). Ligand 1 coordinates to [Fe(OH2)6](BF4)2 or [Fe(MeCN)6](SbF6)2 in acetonitrile to give the dicationic complex [Fe(MeCN)2(1)](X)2 (2) (X = BF4- or SbF6-). The corresponding carbonyl (3), bromocarbonyl (4), and bis(tert-butylisonitrile) (5) derivatives were prepared and fully characterized. Complex 2 reacts with Me3SiCN to give the corresponding trimethylsilyl isocyanide derivative 18 featuring a Fe-CNSiMe3 linkage. The X-ray structures of 2, 3, 5, and 18 show that ligand 1 assumes the Λ-cis-α geometry, which allows comparing the trans influence of these ligands. Complexes 2, 3, 5, and 18 were applied in the asymmetric addition of trimethylsilyl cyanide to azomethine imines (Strecker reaction), whose enantioselectivity reached 22% ee. The low enantioselectivity can be explained on the basis of the Me3SiCN/Me3SiNC isomerization and of the reaction product partially displacing the NPPN ligand from iron.
Phosphine-catalyzed [3+2] cycloaddition reactions of azomethine imines with electron-deficient alkenes: A facile access to dinitrogen-fused heterocycles
Li, Zhen,Yu, Hao,Liu, Honglei,Zhang, Lei,Jiang, Hui,Wang, Bo,Guo, Hongchao
supporting information, p. 1731 - 1736 (2014/03/21)
An efficient method for the phosphine-catalyzed [3+2] cycloaddition reaction of azomethine imines with diphenylsulfonyl alkenes to give dinitrogen-fused bi- or tricyclic heterocyclic compounds in high yields has been described. Moreover, two phenylsulfony
Catalyst-free synthesis of N -(1,7-dioxotetrahydropyrazolo[1,2-a]pyrazol-2- yl)benzamide derivatives by 1,3-dipolar cycloaddition and rearrangement
Liu, Wenjing,Xu, Yu,Sun, Xingxia,Lu, Dapeng,Guo, Lijuan
supporting information, p. 1093 - 1096 (2014/05/20)
N-(1,7-Dioxotetrahydropyrazolo[1,2-a]pyrazol-2-yl)-benzamide derivatives, a novel class of compounds, were synthesized by 1,3-dipolar cycloaddition of azomethine imines with azlactones and subsequent rearrangement. The reaction can be completed rapidly under mild conditions without a catalyst. Georg Thieme Verlag Stuttgart New York.
Enantioselective copper-catalyzed [3+3] cycloaddition of azomethine ylides with azomethine imines
Guo, Hongchao,Liu, Honglei,Zhu, Fu-Lin,Na, Risong,Jiang, Hui,Wu, Yang,Zhang, Lei,Li, Zhen,Yu, Hao,Wang, Bo,Xiao, Yumei,Hu, Xiang-Ping,Wang, Min
supporting information, p. 12641 - 12645 (2013/12/04)
The more dipoles, the merrier: An asymmetric [3+3] cycloaddition of azomethine ylides derived from imines 1 with azomethine imines 2 in the presence of a chiral ferrocenylphosphine-copper catalyst afforded highly functionalized heterocyclic products 3 in high yield with excellent enantio- and diastereoselectivity (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). The 1,3-dipolar reaction partners can be readily prepared from aldehydes. Copyright
Phosphine-catalyzed annulations of azomethine imines: Allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways
Na, Risong,Jing, Chengfeng,Xu, Qihai,Jiang, Hui,Wu, Xi,Shi, Jiayan,Zhong, Jiangchun,Wang, Min,Benitez, Diego,Tkatchouk, Ekaterina,Goddard, William A.,Guo, Hongchao,Kwon, Ohyun
supporting information; experimental part, p. 13337 - 13348 (2011/10/09)
In this paper we describe the phosphine-catalyzed [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] annulations of azomethine imines and allenoates. These processes mark the first use of azomethine imines in nucleophilic phosphine catalysis, producing dinitrogen
A new copper-catalyzed [3 + 2] cycloaddition: Enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles
Shintani, Ryo,Fu, Gregory C.
, p. 10778 - 10779 (2007/10/03)
A copper-catalyzed method for the regioselective 1,3-dipolar cycloaddition of azomethine imines to terminal alkynes has been developed. Through the use of a chiral phosphaferrocene-oxazoline ligand, a wide range of substrates can be coupled to generate us
