33722-47-3Relevant academic research and scientific papers
Palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides
Xu, Boran,Worrall, Kraig,Arndtsen, Bruce A.
, p. 13759 - 13768 (2012)
We describe the palladium-catalyzed multicomponent synthesis of 2-imidazolines. This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation. Decarboxylation in CHCl3 is found to result in a mixture of imidazolinium and imidazolium salts. However, the addition of benzoic acid suppresses aromatization, and generates the trans-disubstituted imidazolines in good yield. Combining this reaction with subsequent nitrogen deprotection provides an overall synthesis of imidazolines from multiple available building blocks.
Catalytic activity of Mg-Al hydrotalcites and derived mixed oxides for imination reactionsviaan oxidative-dehydrogenation mechanism
Vala, Naresh,Joshi, Pradyuman A.,Mishra, Manish
supporting information, p. 8859 - 8868 (2020/06/08)
The catalytic activities of Mg-Al hydrotalcites and derived Mg-Al mixed oxides were studied for the imination of benzylic substrates (benzyl amine and benzyl alcohol), with aniline as a model reaction, to establish a green and cost-effective catalytic (precious metal free) process for imination and tandem reactions utilizing alcohols as reagents. The Mg-Al mixed oxide (Mg/Al ratio = 3.0) was found to be an efficient catalyst for imination reactions to synthesize cross-imines with high selectivity as well as for tandem reactions of alcohols. Basic sites of catalysts adsorb benzylic substrates through the hydrogen of their functional groups (-NH2/-OH) and activate (weaken) benzylic C-H bonds for hydride elimination. Thus, basic sites catalyze the reaction by activating benzylic substrates for oxidative-dehydrogenation (i.e., deprotonation followed by hydride elimination with the help of oxygen) to produce reactive imine/carbonyl intermediates, which undergo subsequent nucleophilic reactions with amine.
Photocatalytic coupling of amines to imidazoles using a Mo-ZnIn2S4 catalyst
Wang, Min,Li, Lihua,Lu, Jianmin,Luo, Nengchao,Zhang, Xiaochen,Wang, Feng
, p. 5172 - 5177 (2017/11/09)
Substituted imidazoles are traditionally synthesized by co-condensation of multiple feedstocks. Herein, we report a new route for the synthesis of substituted imidazoles via photocyclization of readily available amines at room temperature. The reaction is achieved by the visible-light-induced C-C/C-N bond coupling and subsequent dehydrogenation reaction over Mo-ZnIn2S4 as a heterogeneous photocatalyst. A wide range of amines were converted into the corresponding tri- and tetra-substituted imidazoles with up to 96% total yields. The simplicity, high efficiency and mild condition merits of this new reaction will enable it to be useful in synthetic transformations.
Synthesis of tetra-substituted imidazoles and 2-imidazolines by Ni(0)-catalyzed dehydrogenation of benzylic-type imines
Tlahuext-Aca, Adrian,Hernndez-Fajardo, Oscar,Arvalo, Alma,Garca, Juventino J.
, p. 15997 - 16005 (2015/02/02)
Ni(0)-catalyzed dehydrogenation of benzylic-type imines was performed to yield asymmetrical tetra-substituted imidazoles and 2-imidazolines. This was achieved with a single operational step while maintaining good selectivity and atom economy. The catalytic system shows low to moderate tolerance for fluoro-, trifluoromethyl-, methyl-, and methoxy-substituted benzylic-type imines. In addition, the substitution pattern at the N-heterocyclic products was easily controlled by the appropriate selection of R-groups in the starting organic substrates. Based on experimental observations, we propose a reaction mechanism in which benzylic C(sp3)-H bond activation and insertion steps play pivotal roles in this nickel-catalyzed organic transformation. This journal is
Nuclear factor-κB mediated inhibition of cytokine production by imidazoline scaffolds
Kahlon, Daljinder K.,Lansdell, Theresa A.,Fisk, Jason S.,Hupp, Christopher D.,Friebe, Timothy L.,Hovde, Stacy,Jones, A. Daniel,Dyer, Richard D.,Henry, R. William,Tepe, Jetze J.
supporting information; experimental part, p. 1302 - 1309 (2009/12/26)
The mammalian nuclear transcription factor NF-κB is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-α) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-κB has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-κB mediated gene transcription in cell culture as well as inhibitors of TNF-α and IL-6 production in interleukin 1 beta (IL-1β) stimulated human blood.
