- Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid
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Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from α-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We found that, due to the presence of the benzene ring at the C1-position of benzo[4,5]imidazo[1,2-a]pyridines which restricts intramolecular motion, as a new type of aggregation-induced emission (AIE) luminogen (AIEgen), they show very good solid-state fluorescence with quantum yields up to 88.80%. Importantly, the AIE performance of compound3bcan be useful to detect the nitroaromatic explosive picric acid (PA) with a detection limit and quenching constant of 42.5 nM and 7.27 × 104M?M, respectively.
- Yang, Kai,Luo, Shi-He,Chen, Si-Hong,Cao, Xi-Ying,Zhou, Yong-Jun,Lin, Yan-Lan,Huo, Yan-Ping,Wang, Zhao-Yang
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supporting information
p. 8133 - 8139
(2021/10/04)
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- Preparation method 2 -substituted benzimidazole derivative
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The invention belongs to the field of fine chemical product production, and particularly relates to 2 -substituted benzimidazole derivative preparation method which comprises the following steps: (1) taking O-phenylenediamine and aldehyde as raw materials, carrying out catalytic condensation, cyclization and oxidation reaction in a eutectic solvent. (2) Water is added to the reaction system, the separated product is filtered, and the eutectic solvent is recycled. (3) After recrystallization, a target product is obtained. The method has the advantages of simple operation process, easily available raw materials, low cost, high purity of the target product and no catalyst participation, can effectively prevent isomer formation, and is beneficial to large-scale production.
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Paragraph 0088-0093
(2021/11/10)
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- Rhodium catalyzed 2-alkyl-benzimidazoles synthesis from benzene-1,2-diamines and tertiary alkylamines as alkylating agents
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Substituted 2-alkyl-benzimidazoles were synthesized from benzene-1,2-diamine and tertiary amines as alkylating agent under polystyrene supported rhodium (Rh@PS) nanoparticles (NPs) catalyzed conditions. The heterogeneous rhodium catalyst was applied first time for the synthesis of 2-alkyl-benzimidazoles. The reaction followed through oxidation of alkylamines, transamination, and oxidative cyclisation with benzene-1,2-diamines for the corresponding products synthesis with good yields. The process is applicable for vast substrate scope, several functional groups are tolerable, and the Rh@PS catalyst is recyclable up to four cycles without significant loss in catalytic activity.
- Yamini,Sharma, Saurabh,Das, Pralay
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- Sustainable photocatalytic synthesis of benzimidazoles
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Among the 17 Sustainable Development Goals presented by the United Nations in 2015, great attention is devoted to the production of goods and chemicals by use of renewable raw materials, by recycling of products and by extensive use of renewable energy sources. In this context, photocatalysis attracted great attention for the possibility to exploit Solar light to promote the desired chemical reactions. Besides its use in degradation of pollutants and in the production of fuels, some efforts have been devoted in the development of photocatalytic processes for the synthesis of fine chemicals with high added-value. In this work, we investigated the sustainable photocatalytic synthesis of benzimidazole derivatives through a one-pot, tandem process starting from a nitro compound and ethanol. By a photocatalytic approach, ethanol is dehydrogenated producing the hydrogen required for reduction of nitro groups and the aldehyde required for cyclization and production of the benzimidazole unit. Co-doping of TiO2 with B and N is beneficial to increase the photocatalytic activity in H2 production from ethanol. The effect of various metal co-catalysts (Pt, Pd Ag, Cu) have been evaluated on H2 production rate and on selectivity in the synthesis of substituted benzimidazoles: Pt showed the highest selectivity in the desired products while Pd demonstrated a great activity for hydrodehalogenation, with potential interest for degradation of persistent pollutants.
- Montini, Tiziano,Gombac, Valentina,Delgado, Juan J.,Venezia, Anna Maria,Adami, Gianpiero,Fornasiero, Paolo
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- A benzimidazole and synthetic method of derivative thereof (by machine translation)
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The present invention provides a benzimidazole and its derivative synthesis method, the method through the imidazole chloride catalyzed O-phenylenediamine cyclized, realizes the multi-functional chain dibasic and imidazole and 2 - substituted benzimidazole synthesis, method is simple and economic, and the practicability is strong. This invention does not have any other catalyst or additive, synthetic method has good functional group tolerance and excellent yield and purity, reaction time is short, and does not need the harsh reaction conditions, is suitable for industrial production. (by machine translation)
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Paragraph 0045; 0047; 0052; 0053
(2019/02/10)
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- Supported Rhodium (Rh@PS) Catalyzed Benzimidazoles Synthesis Using Ethanol/Methanol as C2H3/CH Source
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An effective and stable polystyrene supported rhodium (Rh@PS) nano-catalyst has been synthesized by following reduction-deposition approach and applied for the selective benzimidazoles synthesis from 1,2-phenylenediamines and ethanol/methanol as C2H3/CH source. The ethanol/methanol in the presence of trace amounts of aerobic oxygen under Rh@PS catalysed condition, first participated in oxidation of alcohol followed by consecutive condensation, cyclization and hydrogen elimination reactions with 1,2-phenylenediamine gave the desired products in good yields. The Rh@PS catalyst in a single system performed both oxidation and reduction reactions in a selective/specific manner and applied for large substrate scope. Easy recovery, handling, stability, recyclability of the catalyst and less chance of metal contamination with the products are the added advantages of the process. (Figure presented.).
- Sharma, Saurabh,Sharma, Ajay,Yamini,Das, Pralay
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supporting information
p. 67 - 72
(2018/12/05)
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- Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives
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A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields.
- Gan, Zongjie,Tian, Qingqiang,Shang, Suqin,Luo, Wen,Dai, Zeshu,Wang, Huajun,Li, Dan,Wang, Xuetong,Yuan, Jianyong
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p. 7450 - 7456
(2018/11/27)
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- Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis
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An oxidant, base and metal free methodology has been developed for the synthesis of various 2-substituted and non-substituted benzazoles, quinazolines and quinazolinones using oxalic/malonic acids as an in situ carbon source. This methodology is applicable for a wide range of substituted o-phenylenediamine, o-aminothiophenol, o-aminophenol and o-aminobenzamide containing various functional groups and provides good to excellent yields of the corresponding product. Furthermore an easy workup procedure, high yield and easy isolation of products are key features of this methodology. The developed protocol is also applicable for the gram scale synthesis of benzimidazoles.
- Sharma, Saurabh,Bhattacherjee, Dhananjay,Das, Pralay
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supporting information
p. 1337 - 1342
(2018/03/06)
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- Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1
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The dCTPase pyrophosphatase 1 (dCTPase) regulates the intracellular nucleotide pool through hydrolytic degradation of canonical and noncanonical nucleotide triphosphates (dNTPs). dCTPase is highly expressed in multiple carcinomas and is associated with cancer cell stemness. Here we report on the development of the first potent and selective dCTPase inhibitors that enhance the cytotoxic effect of cytidine analogues in leukemia cells. Boronate 30 displays a promising in vitro ADME profile, including plasma and mouse microsomal half-lives, aqueous solubility, cell permeability and CYP inhibition, deeming it a suitable compound for in vivo studies.
- Llona-Minguez, Sabin,H?glund, Andreas,Jacques, Sylvain A.,Johansson, Lars,Calderón-Monta?o, José Manuel,Claesson, Magnus,Loseva, Olga,Valerie, Nicholas C. K.,Lundb?ck, Thomas,Piedrafita, Javier,Maga, Giovanni,Crespan, Emmanuele,Meijer, Laurent,Burgos Morón, Estefanía,Baranczewski, Pawel,Hagbj?rk, Ann-Louise,Svensson, Richard,Wiita, Elisee,Alml?f, Ingrid,Visnes, Torkild,Jeppsson, Fredrik,Sigmundsson, Kristmundur,Jensen, Annika Jenmalm,Artursson, Per,Jemth, Ann-Sofie,Stenmark, P?l,Warpman Berglund, Ulrika,Scobie, Martin,Helleday, Thomas
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p. 1140 - 1148
(2016/02/23)
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- Gadolinium (III) chloride catalyzed facile synthesis of 2-substituted benzimidazoles under solvent-free conditions
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A series of 2-substituted benzimidazoles have been prepared from o-diamines and 1,3-dicarbonyl compounds using Gadolinium chloride as a catalyst under solvent free condition in good yields. Gadolinium chloride has been demonstrated as a mild and efficient catalyst.
- Sathaiah,Venkat Lingaiah,Chandra Shekhar,Ravi Kumar,Raju,Shanthan Rao
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p. 953 - 957
(2015/08/19)
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- Benzimidazolium dyes and their use as fluorescent chemosensors
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The present invention is directed toward benzimidazolium dye compounds of formula (I) as follows: wherein, n is an integer from 2-10,m is an integer from 2-10,X1 and X2 are independently a halogen,Q is H or a resin, andR is (aromatic)o-(linker)p-with the linker being saturated or unsaturated C1-C5 hydrocarbons, each aromatic independently being a substituted or unsubstituted aromatic or heteroaromatic, o being 1 or 2, and p being 0 or 1. Methods of making and using these compounds are also disclosed.
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Page/Page column 12
(2014/05/20)
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- Activated alumina ball catalyzed expeditious synthesis of 2-alkylbenzimidazoles with special emphasis on susceptible side chains possessing amide functionality
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A solvent- and chromatography-free, non-hazardous green protocol for the synthesis of 2-alkylbenzimidazoles has been developed under neutral conditions with water as the only by-product. Activated alumina balls, which have been shown previously to assist in amidation reaction, also catalyze very successfully the condensation of benzene-1,2-diamines with carboxylic acids to produce the corresponding benzimidazoles. This methodology is also applicable to susceptible side chains possessing an amide functionality.
- Ghosh, Sabari,Hudrlik, Anne,Mukhopadhyay, Chhanda
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p. 1737 - 1748
(2014/01/17)
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- One-pot synthesis of benzimidazoles by simultaneous photocatalytic and catalytic reactions on Pt@TiO2 nanoparticles
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"Chemical Equation Presented" Dual platinum action: A one-pot catalytic synthesis of benzimidazoles from the photoirradiation of an alcohol solution containing an ortho-arylenediamine and Pt@TiO2 nanoparticles is described. This reaction proceeded by the platinumassisted photocatalytic oxidation of an alcohol and a catalytic dehydrogenation of the intermediates on the surface of platinum nanoparticles.
- Shiraishi, Yasuhiro,Sugano, Yoshitsune,Tanaka, Shunsuke,Hirai, Takayuki
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supporting information; experimental part
p. 1656 - 1660
(2010/06/16)
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- Combinatorial synthesis of benzimidazolium dyes and its diversity directed application toward GTP-selective fluorescent chemosensors
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Highly selective fluorescence turn-on GTP sensor, GTP Green, was discovered by a diversity directed sensor approach, combined by solid-phase combinatorial synthesis of a benzimidazolium library and high-throughput screening. Copyright
- Wang, Shenliang,Chang, Young-Tae
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p. 10380 - 10381
(2007/10/03)
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- Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.
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Compounds 1-18 have been synthesized and tested in vitro against the protozoa Giardia lamblia, Entamoeba histolytica and the helminth Trichinella spiralis. Inhibition of rat brain tubulin polymerization was also measured and compared for each compound. Results indicate that most of the compounds tested were more active as antiprotozoal agents than Metronidazole and Albendazole. None of the compounds was as active as Albendazole against T. spiralis. Although only compounds 3, 9 and 15 (2-methoxycarbonylamino derivatives) inhibited tubulin polymerization, these were not the most potent antiparasitic compounds.
- Valdez, Juan,Cedillo, Roberto,Hernandez-Campos, Alicia,Yepez, Lilian,Hernandez-Luis, Francisco,Navarrete-Vazquez, Gabriel,Tapia, Amparo,Cortes, Rafael,Hernandez, Manuel,Castillo, Rafael
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p. 2221 - 2224
(2007/10/03)
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- Phthalone derivatives utilizable as pigments
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Phthalones derived from benzimidazole can be represented by one of the following general formulas: STR1 in which A1 and A2 each represents an aliphatic, alicyclic, aromatic or heterocyclic radical, possibly substituted by one or more nonsolubilizing substituents, and each of the benzene nuclei B1 and B2 can bear one or two substituents selected from halogen atoms and the lower alkyl, lower alkoxy, nitro, acylamino and aryl groups or be coupled with another benzene nucleus. These phthalones are valuable pigments for textile printing and for coloring inks, lacquers, paints, varnishes and plastic materials.
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