- Anthrathiadiazole Derivatives: Synthesis, Physical Properties and Two-photon Absorption
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Anthrathiadiazole is a key synthon for the construction of large azaacenes, however, the attachment of different substituents onto the skeleton of anthrathiadiazole is difficult but highly desirable because it could be easy to enrich the structures of aza
- Fan, Mingxuan,Chen, Guangsheng,Xiang, Yu,Li, Junbo,Yu, Xianglin,Zhang, Wenying,Long, Xueting,Xu, Liang,Wu, Jinjun,Xu, Ze,Zhang, Qichun
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p. 10898 - 10902
(2021/06/28)
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- Chiral tetrahydrofuran oxazine fused benzimidazole-4, 7-diketone derivative as well as preparation method and application thereof
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The invention discloses a chiral tetrahydrofuran oxazine fused benzimidazole-4, 7-diketone derivative and a preparation method and application thereof, and belongs to the field of sugar chemistry andmedicinal chemistry. The chiral tetrahydrofuran oxazine
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Paragraph 0039-0040
(2020/11/23)
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- Identification of ortho-naphthoquinones as anti-AML agents by highly efficient oxidation of phenols
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A straightforward method for synthesizing ortho-naphthoquinones was identified using an easily available cobalt–Schiff base complex. Efficient oxidation of phenols to ortho-naphthoquinones was useful in obtaining compounds with potent biological activity
- Huang, Huidan,Yan, Ming,Chen, Jianqiu,Yuan, Biao,Chen, Guitang,Cheng, Shujie,Huang, Dechun,Gao, Zhen,Cao, Chongjiang
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- Incorporating Morpholine and Oxetane into Benzimidazolequinone Antitumor Agents: The Discovery of 1,4,6,9-Tetramethoxyphenazine from Hydrogen Peroxide and Hydroiodic Acid-Mediated Oxidative Cyclizations
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The reactivity of hydrogen peroxide and catalytic hydroiodic acid toward 3,6-dimethoxy-2-(cycloamino)anilines is tunable to give ring-fused benzimidazoles or 1,4,6,9-tetramethoxyphenazine in high yield. Mechanisms via a detected nitroso-intermediate are p
- Conboy, Darren,Mirallai, Styliana I.,Craig, Austin,McArdle, Patrick,Al-Kinani, Ali A.,Barton, Stephen,Aldabbagh, Fawaz
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p. 9811 - 9818
(2019/08/20)
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- Light-actuated resorcin[4]arene cavitands
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A light-actuated resorcin[4]arene cavitand equipped with two quinone (Q) and two opposite Ru(II)-based photosensitizing walls was synthesized and investigated. The cavitand is capable of switching from an open to a contracted conformation upon reduction of the two Q to the corresponding SQ radical anions by intramolecular photoinduced electron transfer in the presence of a sacrificial donor. The molecular switch was investigated by cyclic and rotating disc voltammetry, UV–Vis–NIR spectroelectrochemistry, transient absorption, NMR, and EPR spectroscopy. This study provides the basis for the development of future light-activated switches and molecular actuating nanodevices.
- García-López, Víctor,Mili?, Jovana V.,Zalibera, Michal,Neshchadin, Dmytro,Kuss-Petermann, Martin,Ruhlmann, Laurent,Nomrowski, Julia,Trapp, Nils,Boudon, Corinne,Gescheidt, Georg,Wenger, Oliver S.,Diederich, Fran?ois
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supporting information
p. 5615 - 5626
(2018/08/24)
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- Multispectroscopic and theoretical studies on rapid, selective and sensitive visual sensing of cyanide ion in aqueous solution by receptors possessing varying HBD property
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Three new benzoquinone–imidazole ensembles possessing varying number (0, 1 and 2) of electron-withdrawing bromo substituents on the quinone ring have been designed, synthesized, characterized and employed as receptors in cyanide sensing. These receptors c
- Raja Lakshmi,Manivannan,Jayasudha,Elango, Kuppanagounder P.
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p. 2807 - 2821
(2018/01/27)
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- A pyridyl-benzimidazole based molecular luminescent turnstile
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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.
- Godde, Bérangère,Ritaine, Dialia,Jouaiti, Abdelaziz,Mauro, Matteo,Hosseini, Mir Wais
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p. 7810 - 7815
(2018/05/24)
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- Method for nitrating aromatic compound by using nitrate under the action of auxiliary agent
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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.
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Paragraph 0075; 0076
(2018/09/11)
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- Greener synthesis using hydrogen peroxide in ethyl acetate of alicyclic ring-fused benzimidazoles and anti-tumour benzimidazolequinones
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Environmentally-friendly and cost effective hydrogen peroxide in ethyl acetate was used to prepare in high yields pyrrolo[1,2-a]benzimidazoles from commercial o-(pyrrolidin-1-yl)anilines without the requirement for organic-aqueous extraction and chromatography. Six, seven and eight membered ring-fused analogues were similarly obtained in high yields with methanesulfonic acid required for the pyrido[1,2-a]benzimidazole. Anti-tumour benzimidazolequinone derivatives were obtained in high yield via the cyclization of 3,6-dimethoxy-2-(cycloamino)anilines.
- Aldabbagh, Fawaz,Gurry, Michael,Keane, Lee-Ann J.,Sweeney, Martin
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supporting information
p. 3565 - 3567
(2017/10/06)
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- Exploration of the Photodegradation of Naphtho[2,3-g] quinoxalines and Pyrazino[2,3-b]phenazines
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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.
- Kolmer-Anderl, Nicole,Kolmer, Andreas,Thiele, Christina M.,Rehahn, Matthias
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supporting information
p. 5277 - 5287
(2016/04/09)
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- Synthesis, anticancer activity and UPLC analysis of the stability of some New Benzimidazole-4,7-dione derivatives
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In this work, a sensitive analytical method to study the stability of two new series of synthesized heterocyclic compounds, the benzimidazole-4,7-diones 5 and N-oxide benzimidazole-4,7-dione derivatives 6 was established and validated. These derivatives w
- Blaszczak-Swiatkiewicz, Katarzyna,Almeida, Diogo Correia,De Jesus Perry, Maria,Mikiciuk-Olasik, Elzbieta
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p. 400 - 413
(2014/02/14)
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- Diastereospecific enolate addition and atom-efficient benzimidazole synthesis for the production of l/t calcium channel blocker act-280778
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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).
- Funel, Jacques-Alexis,Brodbeck, Stephan,Guggisberg, Yves,Litjens, Remy,Seidel, Thomas,Struijk, Martin,Abele, Stefan
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p. 1674 - 1685
(2015/02/05)
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- Aceno[2,1,3]thiadiazoles for field-effect transistors: Synthesis and crystal packing
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An efficient synthetic approach to a series of aceno[2,1,3]thiadiazole derivatives is described. 2-TIPS and 2-TES molecules exhibited different crystal packings, and 2-TIPS show good device performances with hole mobility up to 0.4 cm2 V-1 s-1 and an average mobility of 0.15 cm2 V-1 s-1 as the active material for organic field-effect transistors. All of the results demonstrate these aceno[2,1,3]thiadiazole derivatives as promising materials for optoelectronic devices.
- Lei, Ting,Zhou, Yan,Cheng, Chu-Yang,Cao, Yue,Peng, Yang,Bian, Jiang,Pei, Jian
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supporting information; experimental part
p. 2642 - 2645
(2011/07/08)
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- Regioselectivity in the nitration of dialkoxybenzenes
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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
- Shopsowitz, Kevin,Lelj, Francesco,MacLachlan, Mark J.
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experimental part
p. 1285 - 1294
(2011/04/26)
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- Photoinduced ligand transformations in a ruthenium complex of dimethoxytetrapyridotetraazapentacene
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The dinuclear ruthenium(ii) complex [(phen)2Ru(tatpOMe)Ru(phen) 2]4+ (24+; phen is 1,10-phenanthroline and tatpOMe is 10,21-dimethoxy-9,10,20,33-tetraazatetrapyrido[3,2-a: 2′3′-c:3′′,2′′-l:2′′′, 3′′′-n]pentacene
- Singh, Shreeyukta,De Tacconi, Norma R.,Boston, David,MacDonnell, Frederick M.
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scheme or table
p. 11180 - 11187
(2011/01/12)
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- Design, synthesis, and cytotoxicity of indolizinoquinoxaline-5,12-dione derivatives, novel DNA topoisomerase IB inhibitors
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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.
- Shen, De-Qing,Wu, Ning,Li, Yan-Ping,Wu, Zu-Ping,Zhang, Hong-Bin,Huang, Zhi-Shu,Gu, Lian-Quan,An, Lin-Kun
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experimental part
p. 1116 - 1121
(2011/03/21)
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- Synthesis of quinoxaline quinones and regioselectivity in their Diels-Alder cycloadditions
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A facile synthesis of quinoxaline quinones is reported. The regioseleclivily in their Dicls-Alder cycloaddition reactions has been investigated at AM I level using Gaussian 98 and MOPAC 6 programs. The products have been characterized from their spectral
- Sharma, Gitanjali,Raisinghani, Pankaj,Abraham, Ignatious,Pardasani,Mukherjee, Tulsi
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scheme or table
p. 1590 - 1596
(2010/03/25)
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- Synthesis of 3,6-dimethoxybenzene-1,2-diamine and of 4,7-dimethoxy-2- methyl-1H-benzimidazole
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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
- Besset, Tatiana,Morin, Christophe
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experimental part
p. 1753 - 1756
(2009/12/09)
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- Aromatic nitration in liquid Ag0.51K0.42Na 0.07NO3
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(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.
- Mascal, Mark,Yin, Lunxiang,Edwards, Ross,Jarosh, Michael
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p. 6148 - 6151
(2008/12/22)
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- The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase
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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.
- Morin, Christophe,Besset, Tatiana,Moutet, Jean-Claude,Fayolle, Martine,Brueckner, Margit,Limosin, Daniele,Becker, Katja,Davioud-Charvet, Elisabeth
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scheme or table
p. 2731 - 2742
(2009/02/03)
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- Synthesis and properties of 2,3-dialkynyl-1,4-benzoquinones
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Alkynyl substituents can be used to tune the acceptor properties of benzoquinones due to their slight electron-withdrawing abilities. Applications of new acceptors rely on efficient and practical synthetic procedures. Herein we describe a general and conv
- Hammershoj, Peter,Reenberg, Theis K.,Pittelkow, Michael,Nielsen, Christian B.,Hammerich, Ole,Christensen, Jorn B.
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p. 2786 - 2794
(2007/10/03)
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- An improved methodology for the preparation of 4,7-dimethoxy-1H- benzimidazole, a key intermediate in the synthesis of 1-alkyl-1H-benzimidazole- 4,7-diones
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We reported an optimized process for the preparation of key intermediate, 4,7-dimethoxy-1H-benzimidazole, from commercially available 1,4-dimethoxybenzene (Overall yield 52%). We successfully applied this methodology to an improved synthesis of 1-benzyl-1
- Taleb, Abbass,Alvarez, Frederic,Nebois, Pascal,Walchshofer, Nadia
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p. 111 - 114
(2007/10/03)
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- Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase
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Benzimidazole-4,7-diones derivatives substituted at 1- and/or 2-position have been synthetized and tested as inhibitors of purine nucleoside phosphorylase (PNP), isolated from two strains of Toxoplasma gondii (RH and ME 49). They were identified as inhibi
- Alvarez, Frédéric,Ghérardi, Arnaud,Nebois, Pascal,Sarciron, Marie-Elizabeth,Pétavy, Anne-Fran?oise,Walchshofer, Nadia
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p. 977 - 979
(2007/10/03)
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- Reaction of 2,5-dimethylpyrroles with quinones. Synthesis of new pyrrolylquinones dyes
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The reaction of 1,4-naphthoquinone (1) with 2,5-dimethylpyrroles (7a-7d) gives only 3-(1,4-naphthoquinonyl)-2,5-dimethylpyrroles. Extending the reaction to other quinones: 5-hydroxy-1,4-naphthoquinone (2), 1,2-naphthoquinone (3), quinoline-5,8-dione (4) and quinoxaline-5,8-dione (5), of which nothing was known, allows the synthesis of new pyrrolylquinones.
- Lion, Claude,Baudry, Richard,Hedayatullah, Mir,Da Conceicao, Louis,Genard, Sylvie,Maignan, Jean
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p. 125 - 130
(2007/10/03)
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- A mild one-pot procedure for the polynitration of activated arenes. Convenient preparation of dinitro- and trinitrodialkoxybenzenes
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When first treated with an excess of nitrogen dioxide alone and then in the presence of ozone at low temperature, dialkoxybenzenes are smoothly and stepwise polynitrated in a one-pot manner to afford the corresponding dinitro or trinitro derivatives in good yield.
- Nose,Suzuki
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p. 1539 - 1542
(2007/10/03)
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- Development of novel quinone phosphorodiamidate prodrugs targeted to DT-diaphorase
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A series of naphthoquinone and benzimidazolequinone phosphorodiamidates has been synthesized and studied as potential cytotoxic prodrugs activated by DT-diaphorase. Reduction of the quinone moiety in the target compounds was expected to provide a pathway for expulsion of the phosphoramide mustard alkylating agent. All of the compounds synthesized were excellent substrates for purified human DT-diaphorase (k(cat)/K(m) = 3 x 107 - 3 x 108 M-1 s-1). The naphthoquinones were toxic to both HT-29 and BE human colon cancer cell lines in a clonogenic assay; however, cytotoxicity did not correlate with DT-diaphorase activity in these cell lines. The benzimidazolequinone analogues were 1-2 orders of magnitude less cytotoxic than the naphthoquinone analogues. Chemical reduction of the naphthoquinone led to rapid expulsion of the phosphorodiamidate anion; in contrast, the benzimidazole reduction product was stable. Michael addition of glutathione and other sulfur nucleophiles provides an alternate mechanism for activation of the naphthoquinone phosphorodiamidates, and this mechanism may contribute to the cytotoxicity of these compounds.
- Flader,Liu,Borch
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p. 3157 - 3167
(2007/10/03)
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- The nitration of electron-rich aromatics
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The successful mononitration of a variety of electron-rich aromatic substrates is reported, employing either nitronium tetrafluoroborate or 'claycop' as the nitrating agent. Dinitration of four of the substrates was achieved when employing nitronium tetrafluoroborate. Several of the products have previously been prepared only by indirect methods.
- Dwyer,Holzapfel
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p. 7843 - 7848
(2007/10/03)
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- Electron Transfer and Ion Pairing, 18 ; Radical Anions and Radical Ion Pairs of Aza-Substituted Naphtho- and Anthraquinones
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The redox behaviour of aza-substituted naphtho- and anthraquinones, which offer O=C-C=N- chelate tongs for an advantageous five-membered ring metal cation complexation, is investigated by a combination of cyclovoltametric and ESR/ENDOR spectroscopic measurements.The formation of paramagnetic contact ion pairs like .-Me+>., with Me+ = Li+, Na+, Tl+, or of triple ion radical cations like -Me2+>.+ with Me+ = Li+, Na+ is corroborated both by shifts of the second reduction potential of up to 0.67 V for e.g. quinoline 5,8-quinone upon additon of Li+- to its DMF solution and by the observation of ESR/ENDOR metal cuplings.
- Bock, H.,Dickmann, P.,Herrmann, H.-F.
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p. 326 - 338
(2007/10/02)
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- Heterocyclic Systems Containing Brigdehead Nitrogen Atom: Part LII - Synthesis of 6,7-Dimethoxy and 5,8-Dimethoxy Thiazolobenzimidazol-3(2H)-ones, Thiazolobenzimidazoles and 2,3-Dihydrothiazolobenzimidazoles
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5,6-Dimethoxy- (IIIa) and 4,7-dimethoxy-2-mercaptobenzimidazoles (IIIb), obtained by the successive reactions involving nitration of dimethoxybenzenes (Ia,b), reduction of the o-dinitrobenzenes (IIa,b) with Raney nickel and hydrazine hydrate followed by t
- Narayan, Sat,Kumar, Vinod,Pujari, H. K.
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p. 267 - 270
(2007/10/02)
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