56741-26-5Relevant articles and documents
A pyridyl-benzimidazole based molecular luminescent turnstile
Godde, Bérangère,Ritaine, Dialia,Jouaiti, Abdelaziz,Mauro, Matteo,Hosseini, Mir Wais
, p. 7810 - 7815 (2018/05/24)
A molecular turnstile T1 based on a luminescent pyridyl-benzimidazole stator and a rotor containing a pyridyl coordinating site is designed and its multi-step synthesis is described. The turnstile T1 undergoes free rotation of the rotor around the stator.
Method for nitrating aromatic compound by using nitrate under the action of auxiliary agent
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Paragraph 0075; 0076, (2018/09/11)
The invention discloses a method for nitrating an aromatic compound by using a nitrate under the action of an auxiliary agent, and provides an aromatic nitro compound preparation method, which comprises: in the presence of an external action and an auxiliary agent, carrying out a nitrating reaction on an aromatic compound and a metal nitrate or a hydrate thereof to obtain the aromatic nitro compound, wherein the external action can cause the physical and/or chemical property change of a substance, the auxiliary agent is a substance having water absorbing ability, the external action can be mechanical force or heating, and the mechanical force can be any one selected from compression, shearing, impacting, friction, stretching, bending and vibration. According to the present invention, the method does not require any solvents so as to avoid the generation of the waste liquid; the acidic substance is not used, such that the treatment is simple after the reaction is completed, and the equipment is not damaged; the added auxiliary agent can be theoretically recycled; and the method has extremely high conversion rate and extremely high selectivity, and can be used for the nitration of conventional aromatic compounds.
Exploration of the Photodegradation of Naphtho[2,3-g] quinoxalines and Pyrazino[2,3-b]phenazines
Kolmer-Anderl, Nicole,Kolmer, Andreas,Thiele, Christina M.,Rehahn, Matthias
supporting information, p. 5277 - 5287 (2016/04/09)
Nitrogen-containing polycyclic aromatic hydrocarbons are very attractive compounds for organic electronics applications. Their low-lying LUMO energies points towards a potential use as n-type semiconductors. Furthermore, they are expected to be more stable under ambient conditions, which is very important for the formation of semiconducting films, where materials with high purity are needed. In this study, the syntheses of naphtho[2,3-g]quinoxalines and pyrazino[2,3-b]phenazines is presented by using reaction conditions, that provide the desired products in high yields, high purity and without time-consuming purification steps. The HOMO and LUMO energies of the compounds are investigated by cyclic voltammetry and UV/Vis spectroscopy and their dependency on the nitrogen content and the terminal substituents are examined. The photostability and the degradation pathways of the naphtho[2,3-g]quinoxalines and pyrazino[2,3-b]phenazines are explored by NMR spectroscopy of irradiated samples affirming the large influence of the nitrogen atoms in the acene core on the degradation process during the irradiation. Finally, by identifying the degradations products of 2,3-dimethylnaphtho[2,3-g]quinoxaline it is possible to track down the most reactive position in the compound and, by blocking this position with nitrogen, to strongly increase the photostability.
Diastereospecific enolate addition and atom-efficient benzimidazole synthesis for the production of l/t calcium channel blocker act-280778
Funel, Jacques-Alexis,Brodbeck, Stephan,Guggisberg, Yves,Litjens, Remy,Seidel, Thomas,Struijk, Martin,Abele, Stefan
, p. 1674 - 1685 (2015/02/05)
A scalable access to 1 (ACT-280778), a potent L/T calcium channel blocker, has been developed. The synthesis, amenable to kilogram manufacturing, comprises 10 chemical steps from enantiomerically pure 5-phenylbicyclo[2.2.2]oct-5-en-2-one (3) and 1,4-dimethoxybenzene with a longest linear sequence of 7 steps. Key to the success of this fit-for-purpose approach are a robust and atom-efficient access to benzimidazole 4, the substrate-controlled diastereoselective enolate addition toward carboxylic acid 2 that was isolated by simple crystallization with high dr (>99:1), the convenient selective N-deacylation of intermediate 10, and the identification of a suitable solid form of 1 as the bis-maleate salt (1·2 C4H4O4). As an illustration of the robustness of this process, 14 kg of drug substance, suitable for human use, was produced with an overall yield of 38% over the longest linear sequence (7 steps).
Regioselectivity in the nitration of dialkoxybenzenes
Shopsowitz, Kevin,Lelj, Francesco,MacLachlan, Mark J.
experimental part, p. 1285 - 1294 (2011/04/26)
Dinitrodialkoxybenzene derivatives are important precursors for Schiff base macrocycles and a variety of other molecules. During our investigations, we have found that the dinitration reaction of 1,2-dialkoxybenzenes proceeds with unusual regioselectivity
Design, synthesis, and cytotoxicity of indolizinoquinoxaline-5,12-dione derivatives, novel DNA topoisomerase IB inhibitors
Shen, De-Qing,Wu, Ning,Li, Yan-Ping,Wu, Zu-Ping,Zhang, Hong-Bin,Huang, Zhi-Shu,Gu, Lian-Quan,An, Lin-Kun
experimental part, p. 1116 - 1121 (2011/03/21)
A series of new indolizinoquinoxaline-5,12-dione derivatives were designed and synthesized via a heterocyclization reaction of 6,7-dichloroquinoxaline-5,8- dione with active methylene reagents and pyridine derivatives. The synthesized compounds exhibited significant activity to inhibit the growth of four human tumour cell lines, including lung adenocarcinoma cell, large-cell lung carcinoma cell, breast carcinoma cell, and ardriamycin-resistant breast carcinoma cell at micromolar range. These compounds were also investigated for their inhibition to DNA topoisomerase IB activity. The results indicated that the indolizinoquinoxaline-5,12-dione structure might be a potential pharmacophore in anti-cancer drug design.
Synthesis of 3,6-dimethoxybenzene-1,2-diamine and of 4,7-dimethoxy-2- methyl-1H-benzimidazole
Besset, Tatiana,Morin, Christophe
experimental part, p. 1753 - 1756 (2009/12/09)
Hydrogenation of a mixture of ortho- and para-dinitro derivatives of 1,4-dimethoxybenzene in ethyl acetate under palladium catalysis, allows 3,6-dimethoxybenzene-1,2-diamine to be isolated as the sole product; this diamine is then converted into 4,7-dimet
Aromatic nitration in liquid Ag0.51K0.42Na 0.07NO3
Mascal, Mark,Yin, Lunxiang,Edwards, Ross,Jarosh, Michael
, p. 6148 - 6151 (2008/12/22)
(Figure Presented) Aromatic molecules have a strong affinity for silver(I) and dissolve to a limited extent in Ag0.51K0.42Na 0.07NO3, a low-melting eutectic mixture of silver, potassium, and sodium nitrates. Aromatic nitration in this inorganic ionic liquid leads to products which arise from nonelectrophilic substitution pathways.
The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase
Morin, Christophe,Besset, Tatiana,Moutet, Jean-Claude,Fayolle, Martine,Brueckner, Margit,Limosin, Daniele,Becker, Katja,Davioud-Charvet, Elisabeth
scheme or table, p. 2731 - 2742 (2009/02/03)
Various aza-analogues of 1,4-naphthoquinone and menadione were prepared and tested as inhibitors and substrates of the plasmodial thioredoxin and glutathione reductases as well as the human glutathione reductase. The replacement of one to two carbons at the phenyl ring of the 1,4-naphthoquinone core by one to two nitrogen atoms led to an increased oxidant character of the molecules in accordance with both the redox potential values and the substrate efficiencies. Compared to the 1,4-naphthoquinone and menadione, the quinoline-5,8-dione 1 and both quinoxaline-5,8-diones 5 and 6 behaved as the most efficient subversive substrates of the three NADPH-dependent disulfide reductases tested. Modulation of these parameters was observed by alkylation of the aza-naphthoquinone core. The Royal Society of Chemistry.
Dynamic [2]catenanes based on a hydrogen bonding-mediated bis-zinc porphyrin foldamer tweezer: A case study
Wu, Jing,Fang, Fang,Lu, Wen-Ya,Hou, Jun-Li,Li, Chuang,Wu, Zong-Quan,Jiang, Xi-Kui,Li, Zhan-Ting,Yu, Yi-Hua
, p. 2897 - 2905 (2008/02/02)
(Chemical Equation Presented) This paper describes the self-assembly of a new class of three-component dynamic [2]catenanes, which are driven or stabilized by intramolecular hydrogen bonding, coordination, and electrostatic interaction. One of the component molecules 2, consisting of an aromatic oligoamide spacer and two peripheral zinc porphyrin units, was designed to adopt a folded preorganized conformation, which is stabilized by consecutive intramolecular three-centered hydrogen bonds. Component molecule 3 is a linear secondary ammonium bearing two peripheral pyridine units, which was designed to form a 1:1 complex with 24-crown-8 (5). The 1H NMR and UV-vis experiments in CDCl3-CD3CN (4:1 v/v) revealed that, due to the preorganized U-shaped feature, 2 could efficiently bind 3 through the cooperative zinc-pyridine coordination to generate highly stable 1:1 complex 2·3. Adding 5 to the 1:1 solution of 2 and 3 led to the formation of dynamic three-component [2]catenane 2·3·5 as a result of the threading of 3 through 5. 1H NMR studies indicated that in the 1:1:1 solution (3 mM) [2]catenane 2·3·5 was generated in 55% yield at 25°C. The yield was increased with the reduction of the temperature and [2]catenane could be produced quantitatively in a 1:1:2 solution ([2] = 3 mM) at -13°C. Replacing 3 with 1,2-bis(4,4′-bipyridinium)ethane (4) in the three-component solution could also give rise to similar dynamic [2]-catenane 2·4·5 albeit in slightly lower yield.