457957-92-5Relevant articles and documents
Solvent- and Catalyst-Free Aza-Michael Addition of Imidazoles and Related Heterocycles
Gobec, Florian,Kodolitsch, Katharina,Slugovc, Christian
, (2020/05/18)
This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80 °C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor, and no additional solvents are necessary for purifying the products.
Ionic liquid catalytic amine with the α, β-unsaturated electron deficient receptor method
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Paragraph 0042-0043, (2017/02/09)
The invention relates to a method for catalyzing amines and alpha, beta-unsaturated electron-deficient acceptors by an ionic liquid. The method comprises the following steps: by taking the ionic liquid as a catalyst, carrying out a catalytic addition reaction on alpha, beta-unsaturated electron-deficient acceptors such as amines, acrylate and acrylonitrile at room temperature and at normal pressure, and carrying out column chromatography to obtain a corresponding addition product; magnetically stirring at room temperature without a solvent, after reaction, extracting the ionic liquid by water and ethyl acetate; carrying out column chromatography on an organic phase to obtain a product; and re-putting the filtrate with the water phase of the ionic liquid without vapor at high temperature in vacuum to react. Through verification, the product can be used as a catalytic reaction system which is repeatedly used for 6 times, and no remarkable reaction yield reduction is discovered. The method is simple to operate, high in yield, good in reusability of the catalytic reaction system and mild reaction condition and has a good industrialized prospect.
Highly efficient and green chemical synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds using nanocrystalline ZSM-5 catalysts
Kore, Rajkumar,Satpati, Biswarup,Srivastava, Rajendra
, p. 8 - 17 (2014/04/03)
A solvent free protocol is developed for the synthesis of imidazolyl alcohols and N-imidazolyl functionalized β-amino compounds. Imidazolyl alcohols were synthesized by the ring opening of epoxides with imidazoles and N-imidazolyl functionalized β-amino compounds were synthesized by the hydroamination reaction of imidazoles and activated olefins. These reactions were catalyzed by a variety of crystalline heterogeneous catalysts such as Al/Zr substituted nanocrystalline ZSM-5 (M-Nano-ZSM-5), conventional M-ZSM-5 (where M = Zr, Al), and Zr substituted amorphous mesoporous catalysts (Zr-SBA-15 and Zr-KIT-6). Among these catalysts, nanocrystalline Zr-Nano-ZSM-5 exhibited the highest activity and regioselectivity. Structure activity relationship is explained based on the catalytic activity, acidity measurements, reactivity of reactants (imidazoles/epoxides/methyl acrylate), competitive adsorption, nature, and type of catalysts. Zr-Nano-ZSM-5 exhibited exceptionally high catalytic activity compared to the catalysts reported in the literature for the synthesis of imidazolyl alcohols and other imidazole derivatives.
Structure-activity studies of divin: An inhibitor of bacterial cell division
Zhou, Maoquan,Eun, Ye-Jin,Guzei, Ilia A.,Weibel, Douglas B.
supporting information, p. 880 - 885 (2013/10/01)
We describe the synthesis and structure-activity relationship (SAR) studies of divin, a small molecule that blocks bacterial division by perturbing the assembly of proteins at the site of cell septation. The bacteriostatic mechanism of action of divin is distinct from other reported inhibitors of bacterial cell division and provides an opportunity for assessing the therapeutic value of a new class of antimicrobial agents. We demonstrate a convenient synthetic route to divin and its analogues, and describe compounds with a 10-fold increase in solubility and a 4-fold improvement in potency. Divin analogues produce a phenotype that is identical to divin, suggesting that their biological activity comes from a similar mechanism of action. Our studies indicate that the 2-hydroxynaphthalenyl hydrazide portion of divin is essential for its activity and that alterations and substitution to the benzimidazole ring can increase its potency. The SAR study provides a critical opportunity to isolate drug resistant mutants and synthesize photoaffinity probes to determine the cellular target and biomolecular mechanism of divin.
Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent
Qian, Chao,Xu, Jian-Ming,Wu, Qi,Lv, De-Shui,Lin, Xian-Fu
, p. 6100 - 6104 (2008/03/12)
A novel and efficient enzymatic promiscuous protocol for aza-Michael addition of aromatic N-heterocycles to α,β-unsaturated compounds has been described. The reactions were catalyzed by promiscuous zinc-active-site acylase in organic solvent at 50 °C. The strategy works with a broad range of N-heterocycles to afford the corresponding Michael adduct with good yields in several hours (0.5-6 h). This catalytic promiscuity is the first example of metal-active-site enzyme-catalyzed aza-Michael addition for aromatic N-heterocycles.
A fast and highly efficient protocol for Michael addition of N-heterocycles to α,β-unsaturated compound using basic ionic liquid [bmIm]OH as catalyst and green solvent
Xu, Jian-Ming,Qian, Chao,Liu, Bo-Kai,Wu, Qi,Lin, Xian-Fu
, p. 986 - 990 (2007/10/03)
A fast and green protocol for the Michael addition of N-heterocycles to α,β-unsaturated compounds at room temperature was developed using a basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, as a catalyst and a reaction medium. The react
N-Methylimidazole as a promising catalyst for the aza-Michael addition reaction of N-heterocycles
Bo, Kai Liu,Wu, Qi,Xue, Qi Qian,De, Shui Lv,Xian, Fu Lin
, p. 2653 - 2659 (2008/02/13)
N-Methylimidazole has been shown to be a promising catalyst for aza-Michael reactions. Various N-heterocycles were introduced to α,β-unsaturated carbonyl compounds employing N-methylimidazole (0.05 equiv) in a highly efficient, rapid and high yielding syn
