cas 670-96-2, 2-Phenylimidazole | Articles data

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Nitrene-like Behaviour of Diazoazoles?
Treatment of 4,5-dicyano-2-diazoimidazole, 2-diazoimidazole, amd 3-diazopyrazole with 1,1-dimethoxyethene affords azolo-as-triazines (1c), (3c), and (8c), respectively; the involvement as intermediates of either aziridines (d), arising from a 'nitrene-like reaction' of diazoazoles, or azoalkenes (b) should be questioned at present.
Farras, Jaume,Vilarrasa, Jaume
p. 1127 - 1129
(1986)
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Palladium-catalyzed hydrodefluorination of fluoroarenes
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Brodney, Michael A.,Gair, Joseph J.,Giroux, Simon,Grey, Ronald L.
p. 131 - 146
(2021/06/18)

A sustainable approach towards the three-component synthesis of unsubstituted 1H-imidazoles in the water at ambient conditions
A green protocol for the synthesis of unsubstituted imidazoles has been demonstrated herein. The reaction is realized using commercially available lipase enzyme, porcine pancreas lipase (PPL) in water. The reaction conditions are selective and mild which helped to tolerate a wide variety of functional groups to give the desired products in good chemical yields. (Figure presented.).
Kapale, Suraj S.,Chaudhari, Hemchandra K.,Mali, Suraj N.,Takale, Balaram S.,Pawar, Hitesh
p. 712 - 716
(2020/05/22)

Base-promoted annulation of amidoximes with alkynes: Simple access to 2,4-disubstituted imidazoles
An efficient construction of imidazole ring by a Cs2CO3-promoied annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synehetic ropte with high atom-utilieation for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Intornal alkynes can also undetgo the annulation to give 2,4,5-trisubstituted imidazoles.
Hua, Ruimao,Iqbal, Muhammad Asif,Lu, Le,Mehmood, Hina
(2020/09/17)

Deprotection of N-tert-Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition–Elimination with 3-Methoxypropylamine
Continued pursuit of functionalized soft-N-donor complexant scaffolds with favorable solubility and kinetics profiles applicable for the separation of the trivalent minor actinides from the lanthanides has attracted significant interest over the last three decades. Recent work from this laboratory resulted in the production of various N-Boc protected [1,2,4]triazinyl-pyridin-2-yl indole Lewis basic procomplexants which necessitated the removal of the indole N-Boc protecting group prior to evaluation of complexant efficacy in separations assays. Traditional deprotection strategies involving trifluoroacetic and other protic and Lewis acids proved unsuccessful in removal of the recalcitrant indole-N-Boc protecting group necessitating the development of a new strategy for deprotection of this complexant class. A serendipitous result facilitated utilization of 3-methoxypropylamine as a mild deprotecting agent for various N-Boc protected heteroarenes via a proposed addition–elimination mechanism. Method development, application to various heteroarenes including indoles, 1,2-indazoles, 1,2-pyrazoles, and related derivatives, a ten-fold scale-up reaction, and experimental evaluation of a preliminary mechanistic hypothesis are reported herein.
Carrick, Jesse D.,Gulledge, Zachary Z.
supporting information

(2020/03/24)

Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring
Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).
Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min
supporting information
p. 3110 - 3115
(2020/07/04)

Rh/TiO2-Photocatalyzed Acceptorless Dehydrogenation of N-Heterocycles upon Visible-Light Illumination
TiO2 is an effective and extensively employed photocatalyst, but its practical use in visible-light-mediated organic synthesis is mainly hindered by its wide band gap energy. Herein, we have discovered that Rh-photodeposited TiO2 nanoparticles selectively dehydrogenate N-heterocyclic amines with the concomitant generation of molecular hydrogen gas in an inert atmosphere under visible light (λmax = 453 nm) illumination at room temperature. Initially, a visible-light-sensitive surface complex is formed between the N-heterocycle and TiO2. The acceptorless dehydrogenation of N-heterocycles is initiated by direct electron transfer from the HOMO energy level of the amine via the conduction band of TiO2 to the Rh nanoparticle. The reaction condition was optimized by examining different photodeposited noble metals on the surface of TiO2 and solvents, finding that Rh0 is the most efficient cocatalyst, and 2-propanol is the optimal solvent. Structurally diverse N-heterocycles such as tetrahydroquinolines, tetrahydroisoquinolines, indolines, and others bearing electron-deficient as well as electron-rich substituents underwent the dehydrogenation in good to excellent yields. The amount of released hydrogen gas evinces that only the N-heterocyclic amines are oxidized rather than the dispersant. This developed method demonstrates how UV-active TiO2 can be employed in visible-light-induced synthetic dehydrogenation of amines and simultaneous hydrogen storage applications.
Bahnemann, Detlef W.,Balayeva, Narmina O.,Dillert, Ralf,Mamiyev, Zamin,Zheng, Nan
p. 5542 - 5553
(2020/08/25)

Imidazole diarylethene switches: An alternative to acid-gated photochromism
We prepared five diarylethenes containing 2-aryl-imidazole as the ethene bridge (L1-L5), and introduced response sites in imidazole rather than in the traditional appended aryl units to regulate their photochromism and thermal stability under acid stimulus. The results show that we can change the thermal stability from P- to T-type, and prevent their photoactivity by acidification, and it is clarified that the stronger the acid or the more acid added, the faster the decay rate of the diarylethene photostability. Furthermore, the prohibited photoactivity could be restored by neutralization with an equimolar amount of base.
Jiang, Yue,Li, Meng-Lian,Xiong, Kang-Tai,Xu, Hai-Bing,Zeng, Ming-Hua
supporting information
p. 8061 - 8067
(2020/06/10)

Visible-Light-Mediated Photocatalytic Aerobic Dehydrogenation of N-heterocycles by Surface-Grafted TiO2 and 4-amino-TEMPO
Herein, the visible-light-induced dehydrogenation of N-heterocycles such as tetrahydroquinolines, tetrahydroisoquinolines, and indolines in O2-containing suspensions of a commercially available titanium dioxide photocatalyst yielding the corresponding heteroarenes is presented. 4-Amino-2,2,6,6-tetramethylpipiridinyloxyl (4-amino-TEMPO) was found to exhibit a beneficial role, as it increased the yield and improved the selectivity of the dehydrogenation reaction. Both the selectivity and the yield are further enhanced by grafting 0.1 wt % of Ni(II) ions onto the TiO2 surface. It is proposed that the basic reactant adsorbs at Lewis acid sites present at the TiO2 surface. The dehydrogenation reaction is initiated by visible-light excitation of the resulting surface complex and a subsequent single-electron transfer from the excited N-heterocycle via the conduction band of TiO2 to O2. Ni(II) ions possibly serve as an electron transfer bridge between the conduction band of TiO2 and O2, while the TEMPO derivative is assumed to act as a selective redox mediator involved in reactions of the generated reactive oxygen species.
Balayeva, Narmina O.,Zheng, Nan,Dillert, Ralf,Bahnemann, Detlef W.
p. 10694 - 10704
(2019/11/14)

Palladium catalyzed hydrodefluorination of fluoro-(hetero)arenes
Palladium catalyzed hydrodefluorination was developed for fine-tuning the properties of fluoro-(hetero)aromatic compounds. The robust reaction can be set up in air, requires only commercially available components, and tolerates a variety of heterocycles and functionalities relevant to drug discovery. Given the prevalence of fluorine incorporation around metabolic hotspots, the corresponding deuterodefluorination reaction may prove useful for converting fluorinated libraries to deuterated analogues to suppress the oxidative metabolism by kinetic isotope effects.
Gair, Joseph J.,Grey, Ronald L.,Giroux, Simon,Brodney, Michael A.
supporting information
p. 2482 - 2487
(2019/04/10)

An Angle on MK2 Inhibition—Optimization and Evaluation of Prevention of Activation Inhibitors
The mitogen-activated protein kinase p38α pathway has been an attractive target for the treatment of inflammatory conditions such as rheumatoid arthritis. While a number of p38α inhibitors have been taken to the clinic, they have been limited by their efficacy and toxicological profile. A lead identification program was initiated to selectively target prevention of activation (PoA) of mitogen-activated protein kinase-activated protein kinase 2 (MK2) rather than mitogen- and stress-activated protein kinase 1 (MSK1), both immediate downstream substrates of p38α, to improve the efficacy/safety profile over direct p38α inhibition. Starting with a series of pyrazole amide PoA MK2 inhibitor leads, and guided by structural chemistry and rational design, a highly selective imidazole 9 (2-(3′-(2-amino-2-oxoethyl)-[1,1′-biphenyl]-3-yl)-N-(5-(N,N-dimethylsulfamoyl)-2-methylphenyl)-1-propyl-1H-imidazole-5-carboxamide) and the orally bioavailable imidazole 18 (3-methyl-N-(2-methyl-5-sulfamoylphenyl)-2-(o-tolyl)imidazole-4-carboxamide) were discovered. The PoA concept was further evaluated by protein immunoblotting, which showed that the optimized PoA MK2 compounds, despite their biochemical selectivity against MSK1 phosphorylation, behaved similarly to p38 inhibitors in cellular signaling. This study highlights the importance of selective tool compounds in untangling complex signaling pathways, and although 9 and 18 were not differentiated from p38α inhibitors in a cellular context, they are still useful tools for further research directed to understand the role of MK2 in the p38α signaling pathway.
Hedstr?m, Ulf,Norberg, Monica,Evertsson, Emma,Lever, Sarah R.,Munck af Rosensch?ld, Magnus,L?nn, Hans,Bold, Peter,K?ck, Helena,Berntsson, Pia,Vinblad, Johanna,Liu, Jianming,Welinder, Anette,Karlsson, Johan,Snijder, Arjan,Pardali, Katerina,Andersson, Ulf,Davis, Andrew M.,Mogemark, Mickael
supporting information
p. 1701 - 1709
(2019/08/21)

LIGHT-EMITTING MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, ORGANIC ELECTROLUMINESCENT DEVICE USING SAME, AND MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE
The present invention relates to a novel compound which has the effect of regulating emission wavelengths and has excellent luminescence efficiency; a production method of the novel compound; and an organic electroluminescence device comprising the novel compound. Accordingly, an organic electroluminescence device using a novel pyrene derivative of the present invention may have significantly improved luminescence efficiency and lifetime.COPYRIGHT KIPO 2019
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Paragraph 0147-0149

(2019/05/25)

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer
Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.
Huang, Yuan-Qiong,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min
supporting information
p. 2065 - 2069
(2018/01/27)

Oxidation Catalysis by an Aerobically Generated Dess–Martin Periodinane Analogue
Hypervalent iodine(V) reagents, such as Dess–Martin periodinane (DMP) and 2-iodoxybenzoic acid (IBX), are broadly useful oxidants in chemical synthesis. Development of strategies to generate these reagents from dioxygen (O2) would immediately enable use of O2 as a terminal oxidant in a broad array of substrate oxidation reactions. Recently we disclosed the aerobic synthesis of I(III) reagents by intercepting reactive oxidants generated during aldehyde autoxidation. In this work, aerobic oxidation of iodobenzenes is coupled with disproportionation of the initially generated I(III) compounds to generate I(V) reagents. The aerobically generated I(V) reagents exhibit substrate oxidation chemistry analogous to that of DMP. The developed aerobic generation of I(V) has enabled the first application of I(V) intermediates in aerobic oxidation catalysis.
Maity, Asim,Hyun, Sung-Min,Wortman, Alan K.,Powers, David C.
supporting information
p. 7205 - 7209
(2018/05/29)

Design, synthesis, structure-activity relationships study and X-ray crystallography of 3-substituted-indolin-2-one-5-carboxamide derivatives as PAK4 inhibitors
We have previously described the identification of indolin-2-one-5-carboxamides as potent PAK4 inhibitors. This study expands the structure-activity relationships on our original series by presenting several modifications in the lead compounds, 2 and 3. A series of novel derivatives was designed, synthesized, and evaluated in biochemical and cellular assay. Most of this series displayed nanomolar biochemical activity and potent antiproliferative activity against A549 and HCT116 cells. The representative compound 10a exhibited excellent enzyme inhibition (PAK4 IC50 = 25 nM) and cellular potency (A549 IC50 = 0.58 μM, HCT116 IC50 = 0.095 μM). An X-ray structure of compound 10a bound to PAK4 was obtained. Crystallographic analysis confirmed predictions from molecular modeling and helped refine SAR results. In addition, Compound 10a displayed focused multi-targeted kinase inhibition, good calculated drug-likeness properties. Further profiling of compound 10a revealed it showed weak inhibitory activity against various isoforms of human cytochrome P450.
Guo, Jing,Zhao, Fan,Yin, Wenbo,Zhu, Mingyue,Hao, Chenzhou,Pang, Yu,Wu, Tianxiao,Wang, Jian,Zhao, Dongmei,Li, Haitao,Cheng, Maosheng
p. 197 - 209
(2018/06/12)

Selective aryl radical transfers into N-heteroaromatics from diaryliodonoium salts with trimethoxybenzene auxiliary
We have found that a series of trimethoxybenzene-based diaryliodonium(III) salts I (ArI+Ar’X-, where Ar = various aryl groups, Ar’ = 2,4,6-trimethoxyphenyl, X- = counterion) can exclusively cause Ar-transfers during the base-induced radical couplings with N-heteroaromatic compounds 1 by working the trimethoxybenzene ring (Ar’) as an inert coupling auxiliary. By the treatment with N-heteroaromatics 1 as the solvent, the metal-free arylations utilizing the specific salts I initiated by solid NaOH upon heating selectively produced the corresponding biaryls 2 in good yields without the formation of the trimethoxybenzene (Ar’) coupling product.
Dohi, Toshifumi,Ueda, Shohei,Hirai, Akiko,Kojima, Yusuke,Morimoto, Koji,Kita, Yasuyuki
p. 1272 - 1284
(2019/11/14)

Carbon-catalyzed Dehydrogenation of Indolines: Detection of Active Intermediate and Exploration of High-performance Catalyst
Metal-free oxidation of indoline using molecular oxygen as an oxidant was investigated. Among various carbon-based catalysts, we found that reduced graphene oxide (rGO) was the most active. Superoxide radical was formed in the course of the reaction. Although graphene oxide (GO) did not function as a catalyst, rGO could be recycled at least 5 times without any structural change.
Morimoto, Naoki,Takeuchi, Yasuo,Nishina, Yuta
supporting information
p. 21 - 23
(2016/01/20)

Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus
We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 μM) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated.
Dong, Jianghong,Chen, Shengwei,Li, Runfeng,Cui, Wei,Jiang, Haiming,Ling, Yixia,Yang, Zifeng,Hu, Wenhui
p. 605 - 615
(2015/12/30)

2-phenyl imidazole of preparation method (by machine translation)
The invention relates to a 2-phenyl imidazole of preparation method, in particular to a pure ammonia, benzald and glyoxal aqueous solution as a raw material, in the micro-pressure lower, pneumatic-liquid-liquid phase method, synthesis of 2-phenyl imidazole. In the gas-liquid-liquid phase synthesis device in an aqueous solution of formaldehyde and biformyl adds the benzene ; on the control temperature, under water, ammonia gas; continue to control the temperature is omitted, control micro-pressure, reaction 12 hours; reaction finishes, evaporate water, cooling, crystallization, filtration, dried to get the product. Because the pneumatic-liquid-liquid phase synthesis device, [...], the contact area of the aqueous phase and organic phase and, that the gas absorption and chemical reaction speed, make the liquid ammonia can be in the low cost atmospheric pressure directly involved in the reaction in the reactor, reduces the energy consumption of the water evaporation after the reaction; also there is no need to add a phase transfer catalyst, reduces the difficulty of the subsequent separation process. (by machine translation)
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Paragraph 0019

(2016/12/26)

Fe3O4/SiO2/(CH2)3N+Me3Br3- core-shell nanoparticles: A novel catalyst for the solvent-free synthesis of five- and six-membered heterocycles
Functionalized magnetic core-shell nanoparticles [Fe3O4/SiO2/(CH2)3N+Me3Br3-] are prepared by co-precipitation method, characterized by transmission electron microscopy, FT-IR, X-ray diffraction, and vibrating sample magnetometer. The catalytic activity of these nanoparticles was tested in the syntheses of imidazole, benzothiazole, and perimidine derivatives, under solvent-free conditions. The catalyst was readily recycled by the use of an external magnetic field and could be reused five times without significant loss of activity or mass.
Farrokhi, Azita,Ghodrati, Keivan,Yavari, Issa
p. 41 - 46
(2015/02/19)

Deprotection of N-benzylbenzimidazoles and N-benzylimidazoles with triethylsilane and Pd/C
The benzyl group is a protecting group for benzimidazoles and imidazoles that can survive acidic, basic, oxidizing, and reducing conditions. Deprotection, however, can require vigorous and potentially non-chemoselective methods. The triethylsilane–Pd/C reduction system is an exceptionally mild, convenient, and efficient method for deprotecting N-benzylbenzimidazoles that are unsubstituted at the 2- and 4-positions as well as suitably substituted N-benzylimidazoles.
Graham, Thomas H.
supporting information
p. 2688 - 2690
(2017/11/14)

Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon
Dehydrogenation of (partially) saturated heterocycles provides an important route to heteroaromatic compounds. A heterogeneous cobalt oxide catalyst, previously employed for aerobic oxidation of alcohols and amines, is shown to be effective for aerobic dehydrogenation of various 1,2,3,4-tetrahydroquinolines to the corresponding quinolines. The reactions proceed in good yields under mild conditions. Other N-heterocycles are also successfully oxidized to their aromatic counterparts.
Iosub, Andrei V.,Stahl, Shannon S.
p. 4404 - 4407
(2015/09/28)

Pd-catalyzed desulfitative and denitrogenative Suzuki-type reaction of arylsulfonyl hydrazides
A palladium-catalyzed desulfitative-denitrogenative coupling of arylsulfonyl hydrazides and arylboronic acids with the assistance of catalytic ligands is described. The reaction showed very good selectivity and tolerated a wide range of functionalities without the aid of expensive copper- or silver-based stoichiometric co-oxidants. We have successfully applied this new cross-coupling reaction to the synthesis of terphenyls and OTBN.
Zhong, Shuangling,Sun, Chenggang,Dou, Sen,Liu, Wencong
p. 27029 - 27033
(2015/03/30)

Reevaluation of the 2-nitrobenzyl protecting group for nitrogen containing compounds: An application of flow photochemistry
Photochemistry under continuous flow conditions has many potential benefits for photochemical reactions that are problematic in batch. The 2-nitrobenzyl moiety is a photolabile protecting group for nitrogen. However, N-deprotection is generally impractical and, therefore, has not been extensively adopted. This Letter reports significant improvements in the N-deprotection of the 2-nitrobenzyl group through the application of continuous flow photolysis. This procedure was applied to a variety of substrates including indoles, indazoles, pyrazoles and secondary amines. Significant improvement in yield, reaction time and scalability was observed under continuous flow conditions.
Wendell, Chloe I.,Boyd, Michael J.
supporting information
p. 897 - 899
(2015/02/05)

One-pot Synthesis of Polysubstituted Imidazoles Catalyzed by an Ionic liquid
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Maleki, Behrooz,Kahoo, Golnoosh Esmailian,Tayebee, Reza
p. 461 - 472
(2015/11/09)

COMPOUNDS FOR TREATMENT OF CANCER
The present invention relates to pharmaceutical compositions for treating cancer comprising BRAF inhibitors, (e.g. vemurafenib) and/or MEK inhibitor, (e.g. trametinib, RO5068760), in combination with anti-tubulin compounds of the invention or other known tubulin inhibitors, and using such compositions for treating cancer such as melanoma, drug-resistant cancer, and cancer metastasis.
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Paragraph 00223; 00246

(2014/09/29)

Multi-wall carbon nanotube supported manganese(III) porphyrin: An efficient and reusable catalyst for oxidation of 2-imidazolines with sodium periodate
The oxidation of 2-substituted imidazolines with sodium periodate catalyzed by tetrakis(p-aminophenyl)-porphyrinatomanganese(III) chloride, [Mn(TNH 2PP)Cl], supported on functionalized multi-wall carbon nanotubes is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by this catalytic system. When the same reaction was subjected to ultrasonic irradiation, the reaction times were reduced significantly and the product yields were increased. This catalyst could be reused several times without significant loss of activity. The effects of reaction parameters such catalyst amount, choice of solvent, and the effects of ultrasonic irradiation on the catalytic activity have been investigated.
Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Rezaei, Simindokht
p. 1 - 5
(2013/08/24)

Copper-catalyzed N -arylation of 2-imidazolines with aryl iodides
The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, ligand-free conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.
Davis, Owen A.,Hughes, Matthew,Bull, James A.
supporting information
p. 3470 - 3475
(2013/06/26)

Ligand modification of cyclometalated ruthenium complexes in the aerobic oxidative dehydrogenation of imidazolines
New cyclometalated ruthenium(III) complexes bearing 2-phenylpyridine derivatives were synthesized and characterized. Chemical modification of the cyclometalating ligand affected its σ-donor character and resulted in regulation of the redox potential of the ruthenium metal center, which was elucidated by X-ray crystallography and cyclic voltammetry. The increase in the electron-donating ability of the cyclometalating ligand improved the catalytic activity of the ruthenium complexes in the aerobic oxidative dehydrogenation of 2-phenylimidazoline, and enabled the catalytic dehydrogenation of 2-phenylimidazoline in air at room temperature. The effect of the ligand structure on the catalytic activity was also elucidated by density functional theory (DFT) calculations and titration experiments.
Aiki, Shota,Kijima, Yuhei,Kuwabara, Junpei,Taketoshi, Ayako,Koizumi, Take-Aki,Akine, Shigehisa,Kanbara, Takaki
p. 812 - 816
(2013/07/25)

A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step
The indole alkaloid α-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group.
Griffiths-Jones, Charlotte M.,Knight, David W.
experimental part
p. 8515 - 8528
(2011/11/29)

Rapid and efficient biomimetic oxidation of 2-imidazolines to their corresponding imidazoles with NaIO4 catalyzed by Mn(salophen)Cl
Rapid and efficient oxidation of 2-substituted imidazolines with sodium periodate is reported. The Mn(III)-salophen/NaIO4 catalytic system efficiently converted 2-imidazolines to their corresponding imidazoles at room temperature in 2: 1, CH3CN/H2O mixture.
Kargar, Hadi
experimental part
p. 863 - 866
(2011/06/25)

Dehydrogenation of 2-imidazolines with sodium periodate catalyzed by manganese(III) tetraphenylporphyrin
In the present work, dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride, [Mn(TPP)Cl], is reported. A wide variety of 2-imidazolines efficiently converted to their corresponding imidazoles by [Mn(TPP)Cl]/NaIO4 catalytic system at room temperature in 1:2, CH3CN/H2O mixture. The effect of reaction parameters such as kind of solvent and catalyst amount was also investigated.
Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Nameni, Iman
experimental part
p. 2146 - 2148
(2011/04/24)

Oxidation of 2-imidazolines to 2-imidazoles with sodium periodate catalyzed by polystyrene-bound manganese(III) porphyrin
In the present work, the dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride supported on polystyrene-bound imidazole, [Mn(TPP)Cl@PSI] is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by the [Mn(TPP)Cl@PSI]/NaIO4 catalytic system in a 1:2 CH3CN/H2O mixture under agitation with magnetic stirring. Ultrasonic irradiation enhanced the catalytic activity of this catalyst in the oxidation of 2-imidazolines and this led to shorter reaction times and higher product yields. This catalyst could be reused several times without significant loss of its catalytic activity.
Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Naghipour, Mahmood
experimental part
p. 1463 - 1468
(2011/06/27)

Aerobic oxidative coupling of amines by carbon nitride photocatalysis with visible light
Coupling on sunshine: A simple and efficient synthesis of benzoxazoles, benzimidazoles, and benzothiazoles is realized through a one-pot preparation driven by a photocatalytic cascade reaction. Carbon nitride and visible light are employed to achieve this metal-free aerobic oxidation of amines to imines (see scheme; mpg-C3N4=mesoporous graphite carbon nitride). Copyright
Su, Fangzheng,Mathew, Smitha C.,Moehlmann, Lennart,Antonietti, Markus,Wang, Xinchen,Blechert, Siegfried
supporting information; experimental part
p. 657 - 660
(2011/03/19)

COMPOUNDS FOR TREATMENT OF CANCER
The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.
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Paragraph 0041; 00356

(2011/10/03)

Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones
A series of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones (111) were synthesized and screened for their antimicrobial and antimycobacterial activities. Further, a series of [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones (1220) reported in our earlier study was also screened for their antimycobacterial activity. The antimycobacterial activity results indicated that [2-(4-Nitro-phenyl)-imidazol- 1-yl]-pyridin-3-yl-methanone (8, minimum inhibitory concentration [MIC]=3.13 g) was equipotent as standard drug ciprofloxacin and [2-(4-Nitro-phenyl)- benzimidazol-1-yl]-pyridin-3-yl-methanone (16, MIC=1.56 g) was equipotent as standard drug ethambutol. The results of antimicrobial screening demonstrated that 2-[1-(Pyridine-3-carbonyl)-1H-imidazol-2-yl]-benzoic acid (compound 11, MIC=0.002 g) was two times more effective than standard drug ciprofloxacin (MIC=0.004 g) against tested bacterial strains and [2-(2,5-Dimethyl-phenyl)- imidazol-1-yl]-pyridin-3-yl-methanone (compound 3, MIC=0.005 g) was equipotent to the reference compound, fluconazole against tested fungal strains.
Narasimhan, Balasubramanian,Sharma, Deepika,Kumar, Pradeep,Yogeeswari, Perumal,Sriram, Dharmarajan
experimental part
p. 720 - 727
(2012/04/04)

PATTERNED FINE PARTICLE FILM STRUCTURES
A patterned fine particle film structure includes a fine particle layer including fine particles arranged and bound to a surface of a substrate coated with a patterned film including a first film compound having a first functional group. The fine particles are coated with films including a first coupling agent having a first coupling reactive group that undergoes a coupling reaction with the first functional group to form a bond. The fine particle layer is bound by a bond formed through a coupling reaction. In an embodiment, fine particles coated with films of a film compound that reacts with the first coupling reactive group and the fine particles are alternately bound to the substrate.
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(2010/06/19)

A convenient procedure for preparing hetarylamides and their analogs by dehydrogenation of the corresponding imidazoles
Conditions of aromatization of 2-(2-hetaryl)imidazolines and their analogs with various dehydrogenating agents were examined. A new catalytic system, Pd/C-diphenyl oxide, was studied, and the optimal catalyst:imidazoline ratio ensuring formation of 2-substituted imidazoles in high yield was found.
Aleksandrov,El'Chaninov
experimental part
p. 1024 - 1026
(2011/01/05)

Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents
A series of 2-aryl-4-benzoyl-imidazoles (ABI) was synthesized as a result of structural modifications based on the previous set of 2-aryl-imidazole-4- carboxylic amide (AICA) derivatives and 4-substituted methoxylbenzoyl-aryl- thiazoles (SMART). The average IC50 of the most active compound (5da) was 15.7 nM. ABI analogues have substantially improved aqueous solubility (48.9 μg/mL for 5ga vs 0.909 μg/mL for SMART-1, 0.137 μg/mL for paclitaxel, and 1.04 μg/mL for combretastatin A4). Mechanism of action studies indicate that the anticancer activity of ABI analogues is through inhibition of tubulin polymerization by interacting with the colchicine binding site. Unlike paclitaxel and colchicine, the ABI compounds were equally potent against multidrug resistant cancer cells and the sensitive parental melanoma cancer cells. In vivo results indicated that 5cb was more effective than DTIC in inhibiting melanoma xenograph tumor growth. Our results suggest that the novel ABI compounds may be developed to effectively treat drug-resistant tumors.
Chen, Jianjun,Wang, Zhao,Li, Chien-Ming,Lu, Yan,Vaddady, Pavan K.,Meibohm, Bernd,Dalton, James T.,Miller, Duane D.,Li, Wei
experimental part
p. 7414 - 7427
(2011/02/23)

Highly active heterogeneous palladium catalyst for the suzuki reaction of heteroaryl chlorides
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Jung, Ji-Young,Taher, Abu,Hossain, Shahin,Jin, Myung-Jong
experimental part
p. 3010 - 3012
(2012/04/17)

Highly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides
Silica gel-supported β-ketoiminatophosphane-Pd complex (Pd@SiO 2) was shown to be a highly active and long-lived catalyst for aqueous Suzuki, Stille and Sonogashira coupling reactions of heteroaryl chlorides. A wide range of heteroaryl chlorides could be efficiently coupled with different nucleophilic partners in the presence of only 0.5 mol% catalyst and under mild conditions. This is one of the most powerful heterogeneous catalysts for the couplings of diverse heteroaryl chlorides. Furthermore, the catalyst could be reused with almost consistent activity. The Royal Society of Chemistry 2010.
Lee, Dong-Hwan,Jung, Ji-Young,Jin, Myung-Jong
experimental part
p. 2024 - 2029
(2011/02/22)

Expanded heterogeneous Suzuki-Miyaura coupling reactions of aryl and heteroaryl chlorides under mild conditions
A mesoporous LTA zeolite (MP-LTA)-supported palladium catalyst was developed for the highly efficient Suzuki-Miyaura reaction of aryl and heteroaryl chlorides. The couplings of various aryl chlorides with arylboronic acids in aqueous ethanol were efficiently achieved in the presence of 1.0 mol% of the catalyst. Furthermore, the scope of this catalyst was extended to the coupling of heteroaryl chlorides. Regardless of the substituents, all of the coupling reactions were very clean and highly efficient under mild heating. It shows that our catalyst is one of the most powerful heterogeneous catalysts for the coupling of a wide range of aryl and heteroaryl chlorides. The catalyst could be repetitively used at least 10 times without a significant loss of its catalytic activity. Compared to mesoporous SBA-15 and MCM-41 materials, the MP-LTA support proved to be very stable and robust to prevent degradation upon reuse.
Lee, Dong-Hwan,Choi, Minkee,Yu, Byung-Woo,Ryoo, Ryong,Taher, Abu,Hossain, Shahin,Jin, Myung-Jong
supporting information; experimental part
p. 2912 - 2920
(2010/04/01)

Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives
In the present study, we have synthesized 2-(substituted phenyl)-1H-imidazole (1-12) and (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanone (13-26) analogues and screened them for their antimicrobial activity against Gram positive, Gram negative and fungal species. The results of antibacterial study indicated that compounds 15, 17 and 24 showed appreciable antibacterial activity and compound 26 emerged as the most potential antifungal agent. The results of SAR studies indicated that the presence of electron withdrawing groups is necessary for the antimicrobial activity of the synthesized compounds. The results of the present study indicated that compounds 15, 17 and 24 might be of interest for the identification of new antimicrobial molecules as their antibacterial activity is equivalent to the standard drug norfloxacin. Further, the antiviral screening of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13-26) against a panel of viral strains indicated that compounds 16 and 19 can be selected as lead compounds for the development of novel antiviral agents.
Sharma, Deepika,Narasimhan, Balasubramanian,Kumar, Pradeep,Judge, Vikramjeet,Narang, Rakesh,De Clercq, Erik,Balzarini, Jan
experimental part
p. 2347 - 2353
(2009/12/03)

Direct Oxidative Conversion of Benzoyl Chlorides to 2-Imidazoles Using Heteropolyacids
The reaction of benzoyl chlorides with ethylenediamine in the presence of catalytic amounts of Keggin-type heteropolyacids led to oxidative conversion of benzoyl chlorides to the corresponding 2-imidazoles in good yields.
Sadjadi, Samaheh,Heravi, Majid M.,Poormohammad, Nargess,Oskooie, Hossein A.,Beheshtiha, Yahya. Sh.,Bamoharram, Fatemeh F.
experimental part
p. 3119 - 3125
(2009/12/01)

A green N-detosylation of indoles and related heterocycles using phase transfer catalysis
A practical method for the N-detosylation of indoles and related heterocycles with KOH in THF and water in the presence of a phase transfer catalyst is described. Using a nonalcoholic solvent, this method prevents the formation of toxic alkyl p-toluene-sulfonate and consequently eliminates the formation of even traces of N-alkyl byproduct. This green method is particularly useful for indoles bearing electron-withdrawing groups and for azaindoles.
Liu, Yugang,Shen, Lichun,Prashad, Mahavir,Tibbatts, Jessica,Repic, Oljan,Blacklock, Thomas J.
p. 778 - 780
(2013/01/03)

Metal-free oxidative dehydrogenation of imidazolines and pyrazolines using silica-adsorbed peroxymonosulfate under aprotic and almost neutral conditions
Oxidative dehydrogenation of 1,3,5-trisubstituted pyrazolines and 2-substituted imidazolines to their corresponding pyrazoles and imidazoles is carried out effectively by treatment with benzyltriphenylphosphonium peroxymonosulfate as an oxidant silica-adsorbed under aprotic and almost neutral conditions.
Adibi,Hajipour,Jafari
experimental part
p. 802 - 806
(2009/04/06)

Palladium(0)-catalyzed, copper(I)-mediated coupling of boronic acids with cyclic thioamides. Selective carbon-carbon bond formation for the functionalization of heterocycles
(Chemical Equation Presented) The palladium-catalyzed cross-coupling of cyclic thioamides with arylboronic acids in the presence of stoichiometric amounts of a copper(I) cofactor is described. The desulfitative carbon-carbon cross-coupling protocol is performed under neutral conditions and can be applied to a range of heterocyclic structures with embedded thioamide fragments. Successful carbon-carbon cross-coupling is independent of the ring size, aromaticity/nonaromaticity, the presence of additional heteroatoms, or other functional groups in the starting thioamide structure. Employing controlled microwave irradiation at 100°C, most cross-couplings can be completed within 2 h and proceed in high yields. An advantage of using thioamides as starting materials is die fact that the system can be tuned to an alternative carbon-sulfur cross-coupling pathway by changing to stoichiometric copper(II) under oxidative conditions. Both types of thioamide cross-couplings are orthogonal to the traditional base-catalyzed Suzuki-Miyaura cross-coupling of aryl halides with boronic acids.
Prokopcova, Hana,Kappe, C. Oliver
p. 4440 - 4448
(2008/02/05)

Desulfitative carbon-carbon cross-coupling of thioamide fragments with boronic acids
A novel and general carbon-carbon cross-coupling reaction between cyclic thioamides and boronic acids is described. The reaction is catalytic in palladium(O) and requires stoichiometric amounts of a copper(I) carboxylate as metal cofactor. The mode of cross-coupling in the reaction of cyclic thioamides with boronic acids is easily tunable between carbon-carbon and carbon-sulfur cross-coupling. While the catalytic palladium(O)/ copper(I) system provides carbon-carbon bond formation with extrusion of sulfur, stoichiometric quantities of copper(II) under air mediate carbon-sulfur bond formation.
Prokopcova, Hana,Kappe, C. Oliver
p. 448 - 452
(2008/02/08)

Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides
The Pd- and Cu-mediated reaction of a large variety of π-electron sufficient heteroarenes, which include free (NH)-imidazoles, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions provides regioselectively the required 2-arylheterocycle derivatives in high yields. 2-Aryl-1-phenyl-1H-imidazoles can also be prepared by a one-pot domino HALEX and Pd- and Cu-mediated arylation reactions of 1-phenyl-1H-imidazole with activated and unactivated aryl bromides under base-free and ligandless conditions. The protocol for the synthesis of 2-arylazoles involving the use of aryl iodides has been found to be suitable for the efficient preparation of three bioactive compounds and a key intermediate in the synthesis of a heparanase inhibitor.
Bellina, Fabio,Calandri, Chiara,Cauteruccio, Silvia,Rossi, Renzo
p. 1970 - 1980
(2007/10/03)

An efficient synthesis of 2-arylimidazoles by oxidation of 2-arylimidazolines using activated carbon-O2 system and its application to palladium-catalyzed Mizoroki-Heck reaction
Oxidative conversion of 2-substituted imidazoline (dihydroimidazole) to the corresponding imidazole was achieved by an activated carbon-O2 system. Also, the 2-arylimidazolines and 2-arylimidazoles have been found to work as simple ligands in the palladium-catalyzed Mizoroki-Heck reaction.
Haneda, Satoshi,Okui, Ayaka,Ueba, Chigusa,Hayashi, Masahiko
p. 2414 - 2417
(2007/10/03)

Synthesis of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles from 1,2-amino alcohols
A highly versatile method for the preparation of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles was developed by using the cyclocondensation reaction of a 1,2-dicarbonyl compound, an aldehyde, a 1,2-amino alcohol, and ammonium acetate.
Matsuoka, Yuki,Ishida, Yasuhiro,Sasaki, Daisuke,Saigo, Kazuhiko
p. 8199 - 8206
(2007/10/03)