cas 615-16-7, 2-Hydroxybenzimidazole | Articles data

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Synthesis of bis(2-imino-1,3-dimethylbenzimidazoline)s via reactions of a solvothermally prepared benzimidazolium chloride and diamines
The first solvothermal preparation of benzimidazolium chloride for the synthesis of bis(2-imino-1,3-dimethylbenzimidazoline) derivatives from readily available diamines is reported, including an optimized preparation of previously reported solvothermal synthesis of the benzimidazolium intermediate. Several primary diamines including both aliphatic and aromatic linkers were converted to the corresponding bis(guanidine)s in moderate to good yield.
Zuo, Shengli,Zhang, Fan,Liu, Jianjun,Zuo, Ang
(2021)
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Preparation of 2(3H)-benzimidazolone and its derivative under aqueous condition as a potential agent for antidiabetic compounds
A focused library of 2(3H)-benzimidazolone and its derivatives has been synthesized in an attempt to identify their antidiabetic potential. All the products have been synthesized under aqueous conditions in lesser time with better yield and purity. A new effective and convenient method for in situ synthesis of five member heterocyclic ring by reaction of phenylene diamine with urea in solvent phase. All the synthesized compounds were characterized by modern spectroscopic techniques.
Abbas, Muhammad Azhar,Hameed, Shahid,Kressler, Joerg
p. 509 - 511
(2013)
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Indium(III)-Catalyzed Synthesis of Primary Carbamates and N-Substituted Ureas
An indium triflate-catalyzed synthesis of primary carbamates from alcohols and urea as an ecofriendly carbonyl source has been developed. Various linear, branched, and cyclic alcohols were converted into the corresponding carbamates in good to excellent yields. This method also provided access to N-substituted ureas by carbamoylation of amines. All the products were obtained by simple filtration or crystallization, without the need for chromatographic purification. Mechanistic investigations suggest that the carbamoylation reaction proceeds through activation of urea by O-coordination with indium, followed by nucleophilic attack by the alcohol or amine on the carbonyl center of urea. The inexpensive and easily available starting materials and catalyst, the short reaction times, and the ease of product isolation highlight the inherent practicality of the developed method.
Jain, Isha,Malik, Payal
supporting information
p. 93 - 97
(2021/11/26)

PrVO4/SnD NPs as a Nanocatalyst for Carbon Dioxide Fixation to Synthesis Benzimidazoles and 2-Oxazolidinones
Recently CO2 stabilization has received a great deal of attention because of its probable applications as a rich C1 resource and the synthesis of several fine chemicals can be accomplished through this stabilization. In this study, Sn(IV) doping dendritic fibrous nanosilica (SnD) supported PrVO4 nanoparticles as a catalyst (PrVO4/SnD) was synthesized by a in-situ procedure. The SnD with the ratios of Si/Sn in a variety of 6 to 40 were acquired through direct hydrothermal synthesis (DHS), and PrVO4 NPs on the surfaces of SnD were reduced in-situ. X-Ray diffraction (XRD), Scanning electron microscope (SEM), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), and X-ray energy dispersive spectroscopy (EDS) were deployed for identifying the PrVO4/SnD. It is potentially a highly dynamic catalyst in the stabilization of CO2 for the production of 2-oxazolidinones and benzimidazoles. In addition, the catalyst is very easy to recycle and reuse without significant loss of active site Cu metal. Graphic Abstract: PrVO4/SnD NPs as a nanocatalyst for carbon dioxide fixation to synthesis benzimidazoles and 2-oxazolidinones. [Figure not available: see fulltext.]
He, Zemin,Yu, Ping,Zhao, Yuzhen,Zhang, Huimin,Zhang, Yongming,Kang, Xiaoxi,Zhang, Haiquan,Sadeghzadeh, Seyed Mohsen
p. 1623 - 1632
(2020/10/19)

CdSnO3/SnD NPs as a Nanocatalyst for Carbonylation of o-Phenylenediamine with CO2
In order to carbonize o-phenylenediamine with CO2, an effective approach was used with UV light irradiation by Sn(IV) doping DFNS (SnD) supported CdSnO3 as a catalyst (CdSnO3/SnD). In this catalyst, SnD with the ratios of Si/Sn in the range of 6 to 50 were obtained using the Direct Hydrothermal Synthesis (DHS), and the nanoparticles of CdSnO3 on the surfaces of SnD were reduced in situ. Scanning Electron Microscope (SEM), X-ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FT-IR), X-ray Energy Dispersive Spectroscopy (EDS), and Transmission Electron Microscopy (TEM) were utilized for characterizing CdSnO3/SnD. It was found that CdSnO3/SnD nanostructures could be used for synthesizing o-phenylenediamines due to their effective and novel catalytic behavior through the reaction between o-phenylenediamines and CO2. Graphic Abstract: [Figure not available: see fulltext.]
Liu, Can,Sadeghzadeh, Seyed Mohsen
p. 2807 - 2815
(2021/02/05)

Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis
Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.
Adamson, Christopher,Kajino, Hidetoshi,Kanai, Motomu,Kawashima, Shigehiro A.,Yamatsugu, Kenzo
supporting information
p. 14976 - 14980
(2021/09/29)

Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2
Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.
Maciejewska, Agnieszka Monika,Paprocki, Daniel,Poznański, Jaros?aw,Speina, El?bieta,Winiewska‐szajewska, Maria
supporting information

(2021/06/09)

Cytotoxic Ruthenium(II) Complexes of Pyrazolylbenzimidazole Ligands That Inhibit VEGFR2 Phosphorylation
Eight new ruthenium(II) complexes of N,N-chelating pyrazolylbenzimidazole ligands of the general formula [RuII(p-cym)(L)X]+ [where the ligand L is 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole (L1) substituted at the 4 position of the pyrazole ring by Cl (L2), Br (L3), or I (L4) and X = Cl- and I-] were synthesized and characterized using various analytical techniques. Complexes 1 and 3 were also characterized by single-crystal X-ray crystallography, and they crystallized as a monoclinic crystal system in space groups P21/n and P21/c, respectively. The complexes display good solution stability at physiological pH 7.4. The iodido-coordinated pyrazolylbenzimidazole ruthenium(II) p-cymene complexes (2, 4, 6, and 8) are more resistant toward hydrolysis and have less tendency to form monoaquated complexes in comparison to their chlorido analogues (1, 3, 5, and 7). The halido-substituted 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole ligands, designed as organic-directing molecules, inhibit vascular endothelial growth factor receptor 2 (VEGFR2) phosphorylation. In addition, the ruthenium(II) complexes display a potential to bind to DNA bases. The cytotoxicity profile of the complexes (IC50 ca. 9-12 μM for 4-8) against the triple-negative breast cancer cells (MDA-MB-231) show that most of the complexes are efficient. The lipophilicity and cellular accumulation data of the complexes show a good correlation with the cytotoxicity profile of 1-8. The representative complexes 3 and 7 demonstrate the capability of arresting the cell cycle in the G2/M phase and induce apoptosis. The inhibition of VEGFR2 phosphorylation with the representative ligands L2 and L4 and the corresponding metal complexes 3 and 7 in vitro shows that the organic-directing ligands and their complexes inhibit VEGFR2 phosphorylation. Besides, L2, L4, 3, and 7 inhibit the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2) and proto-oncogene tyrosine-protein kinase (Src), capable of acting downstream of VEGFR2 as well as independently. Compounds L2, L4, 3, and 7 have a lesser effect on ERK1/2 and more prominently affect Src phosphorylation. We extended the study for L2 and 3 in the Tg(fli1:gfp) zebrafish model and found that L2 is more effective in vivo compared to 3 in inhibiting angiogenesis.
Acharya, Moulinath,Chakraborty, Ayan,Chakraborty, Manas Pratim,Das, Rahul,Koley, Tuhin Subhra,Mukherjee, Arindam,Purkait, Kallol,Roy, Shantanu Saha,Roy, Souryadip
p. 18379 - 18394
(2021/12/01)

Design, Synthesis, Cytotoxicity, and Molecular Docking Studies of New Benzimidazole Hybrids as Possible Anticancer Agents
In the course of efforts to develop new anticancer agents, benzimidazole-based morpholine, thiomorpholine, and piperazine hybrid compounds were designed and synthesized. The structures of the synthesized compounds were confirmed by Proton nuclear magnetic resonance, Carbon-13 NMR, and mass spectroscopy. The title compounds were screened for cytotoxicity against breast and lung cancer cell lines. Compound 6c was found most active against lung cancer cell line with IC50 value of 2.11 μM and compound 10c was found most active against breast cancer cell line with IC50 of 2.23 μM. The molecular docking analysis was also carried out to explore binding pattern of compound with the target protein. All synthesized compounds showed excellent binding affinity toward target protein. Therefore, these findings will be helpful in future drug design of more potent anticancer agents.
Mishra, Shashank Shekher,Sharma, C. S.
p. 21 - 29
(2021/08/12)

Method for preparing carbonyl heterocyclic compound
The invention provides a method for preparing a carbonyl heterocyclic compound, wherein Lewis base and hydrosilane are used as accelerators and can efficiently enable an ortho-substituted aniline compound to react with normal-pressure CO2 to generate corresponding carbonyl heterocyclic compounds containing different functional groups under mild conditions (100 DEG C, digital). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of CO, high-pressure CO2 and noble metal catalysts is avoided, the intermediate isocyanate does not need to be purified and separated, the pure product can be obtained only through simple suction filtration and separation after the reaction is finished, and the synthetic method is efficient and universal, is suitable for preparing a series of benzimidazolone, benzoxazolone and benzothiazolone compounds and has high industrial application value.
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Paragraph 0036-0040

(2020/03/25)

Application of sea urchin-shaped cobalt-based photocatalyst in synthesis of benzoazacycle by converting CO2
The invention relates to the technical field of photocatalysis, in particular to application of a sea urchin-shaped cobalt-based photocatalyst to synthesis of benzoazacycle by converting CO2. A complex is of a sea urchin-shaped microsphere structure, which is composed of an organic ligand L and cobalt nitrate hexahydrate and is formed by arranging a plurality of nano needle-shaped complex crystals. The main body of the organic ligand L is p-aminobenzoic acid; the application comprises the following steps: introducing CO2 into a solution containing o-phenylenediamine compounds, carrying out carbonylation reaction and cyclization with o-phenylenediamine compounds under the action of the urchin-shaped cobalt-based catalyst to generate the benzoazacycle compounds. The sea urchin-shaped microsphere structure cobalt-based catalyst formed by the obtained nano needle-shaped complex crystal has a very large specific surface area and high photocatalytic efficiency; when the photocatalyst is adopted to catalyze and activate CO2, the reaction for synthesizing the benzoazacycle by converting CO2 can be carried out at room temperature, so that the energy consumption is greatly reduced, and the cost is reduced.
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Paragraph 0029-0049

(2020/11/22)

Towards the inhibition of protein–protein interactions (PPIs) in STAT3: Insights into a new class of benzothiadiazole derivatives
Signal transducer and activator of transcription 3 (STAT3) is a validated anticancer target due to the relationship between its constitutive activation and malignant tumors. Through a virtual screening approach on the STAT3-SH2 domain, 5,6-dimethyl-1H,3H-2,1,3-benzothiadiazole-2,2-dioxide (1) was identified as a potential STAT3 inhibitor. Some benzothiadiazole derivatives were synthesized by employing a versatile methodology, and they were tested by an AlphaScreen-based assay. Among them, benzosulfamide 1 showed a significant activity with an IC50 = 15.8 ± 0.6 μM as a direct STAT3 inhibitor. Notably, we discovered that compound 1 was also able to interact with cysteine residues located around the SH2 domain. By applying mass spectrometry, liquid chromatography, NMR, and UV spectroscopy, an in-depth investigation was carried out, shedding light on its intriguing and unexpected mechanism of interaction.
Asai, Akira,Colombo, Diego,Gelain, Arianna,Gilardoni, Ettore,Meneghetti, Fiorella,Mori, Matteo,Parkinson, Gary,Pedretti, Alessandro,Regazzoni, Luca,Villa, Stefania
(2020/08/28)

Synthesis of benzimidazolones by immobilized gold nanoparticles on chitosan extracted from shrimp shells supported on fibrous phosphosilicate
Here we demonstrate the synthesis of benzimidazolones from o-phenylenediamines and carbon dioxide in the presence of gold nanoparticles supported on a composite material based on microcrystalline chitosan from shrimp shells and fibrous phosphosilicate (CS-FPS/Au). The results showed that the gold nanoparticles were stable with the P, N and O atoms of CS-FPS. The morphology and structure of FPS leads to a higher catalytic activity. The CS-FPS/Au NPs were thoroughly characterized using TEM, FESEM, TGA, FTIR, and BET.
Zahedifar, Mahboobeh,Es-Haghi, Ali,Zhiani, Rahele,Sadeghzadeh, Seyed Mohsen
p. 6494 - 6501
(2019/03/14)

Design and Synthesis of Poly(ADP-ribose) Polymerase Inhibitors: Impact of Adenosine Pocket-Binding Motif Appendage to the 3-Oxo-2,3-dihydrobenzofuran-7-carboxamide on Potency and Selectivity
Poly(adenosine 5′-diphosphate-ribose) polymerase (PARP) inhibitors are a class of anticancer drugs that block the catalytic activity of PARP proteins. Optimization of our lead compound 1 ((Z)-2-benzylidene-3-oxo-2,3-dihydrobenzofuran-7-carboxamide; PARP-1 IC50 = 434 nM) led to a tetrazolyl analogue (51, IC50 = 35 nM) with improved inhibition. Isosteric replacement of the tetrazole ring with a carboxyl group (60, IC50 = 68 nM) gave a promising new lead, which was subsequently optimized to obtain analogues with potent PARP-1 IC50 values (4-197 nM). PARP enzyme profiling revealed that the majority of compounds are selective toward PARP-2 with IC50 values comparable to clinical inhibitors. X-ray crystal structures of the key inhibitors bound to PARP-1 illustrated the mode of interaction with analogue appendages extending toward the PARP-1 adenosine-binding pocket. Compound 81, an isoform-selective PARP-1/-2 (IC50 = 30 nM/2 nM) inhibitor, demonstrated selective cytotoxic effect toward breast cancer gene 1 (BRCA1)-deficient cells compared to isogenic BRCA1-proficient cells.
Velagapudi, Uday Kiran,Langelier, Marie-France,Delgado-Martin, Cristina,Diolaiti, Morgan E.,Bakker, Sietske,Ashworth, Alan,Patel, Bhargav A.,Shao, Xuwei,Pascal, John M.,Talele, Tanaji T.
p. 5330 - 5357
(2019/06/07)

Substituted benzimidazoles as modulators of Ras signaling
Benzimidazole compounds that increase the rate of SOS-mediated nucleotide exchange on Ras by binding to a functionally relevant, chemically tractable pocket on the SOS protein, as part of the Ras:SOS:Ras complex.
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Page/Page column 103-104

(2019/12/25)

Chemical synthesis method for 2-hydroxybenzimidazole
The invention discloses a chemical synthesis method for 2-hydroxybenzimidazole. The method comprises the following steps: S1, preparing raw materials and instruments, wherein the raw materials comprise sodium hydrogen sulfite, purified water, aldehyde, o-phenylenediamine, ethanol and TLC (Thin-Layer Chromatography) (spectrum tomography), and the instruments comprise an X4 microscopic melting pointapparatus, a thermometer, a nuclear magnetic resonance spectrometer, an infrared spectrometer and an elemental analyzer; and S2, synthesizing hydroxy sulfonate, namely dissolving 0.1083 mol of sodiumhydrogen sulfite into 14 mL of purified water, stirring for 30 minutes, adding 0.1063 mol of benzaldehyde, stirring and reacting for 0.15 hour, performing suction filtration, washing with 10 mL of purified water, and collecting the white solid a1. The benzaldehyde is reacted with the o-phenylenediamine, the reaction can be completed within 2 hours, the yield is 80% or higher, and due to the reaction between the intermediate hydroxy sulfonate and the o-phenylenediamine, the reaction time is maintained, so that the adhesion of the solid product is spherically dispersed, and the yield is improved.
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Paragraph 0012

(2019/02/26)

An Improved Synthesis of Urea Derivatives from N -Acylbenzotriazole via Curtius Rearrangement
The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N -acyl, and cyclic ureas in good yields from N -acylbenzotriazoles by treating the latter with various amines in the presence of TMSN 3 /Et 3 N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.
Agrahari, Anand K.,Singh, Anoop S.,Singh, Sumit K.,Tiwari, Vinod K.,Yadav, Mangal S.
p. 3443 - 3450
(2019/09/07)

Protonation and Anion Binding Properties of Aromatic Bis-Urea Derivatives—Comprehending the Proton Transfer
A series of aromatic bis-urea derivatives was prepared and their proton dissociation, as well as anion binding properties in DMSO were investigated. To this end, UV/Vis and 1H NMR spectroscopies and computational methods were employed. The synt
Bari?i?, Dajana,Cindro, Nikola,Kulcsár, Marina Juriba?i?,Tireli, Martina,U?arevi?, Krunoslav,Bregovi?, Nikola,Tomi?i?, Vladislav
p. 4695 - 4706
(2019/03/13)

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source
A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.
Qi, Xinxin,Zhou, Rong,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
supporting information
p. 5161 - 5164
(2019/01/25)

Synthesis of Novel Structurally Diverse N-Mono- and N,N′-Disubstituted Benzimidazol-2-one Derivatives by the Alkylations of 1,3-Dihydro-2H-benzimidazol-2-one with Some Alkyl Halides under Transfer Catalysis Conditions
A series of N-mono- and N,N′-disubstituted benzimidazol-2-one derivatives optionally substituted on both secondary amine functionalities were prepared with excellent yields by reacting 1,3-dihydro-2H-benzimidazol-2-one in one and two steps respectively with various alkyl halides under phase transfer catalytic conditions. One of the synthesized N,N-disubstituted benzimidazol-2-one derivatives underwent a regiospecific 1,3-dipolar cycloaddition reaction at its side allyl substituent with the in situ generated 4-chloro benzonitrile N-oxide from 4-chlorobenzaldoxime to afford in good yield the corresponding N,N′-disubstituted derivative incorporating the 2,5-dihydro-isoxazole nucleus in one of the side chain. All the new compounds were fully characterized by their physical and spectroscopic data.
Rohand, Taoufik,Sopbué Fondjo, Emmanuel
p. 2309 - 2314
(2018/09/10)

Method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2
The present invention relates to a method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2. According to the present invention, an inexpensive and easily-available sulfur-containing metal salt compound is first used as an activation catalyst for CO2, and a reaction raw material and CO2 are converted into a corresponding target compound at a low reaction temperature under a low CO2 pressure; and the method has high atomic economy, can reduce the generation of by-products, meets the standards of environmental friendliness and environmentally friendly chemistry, and is the effective way capable of completely utilizing CO2 as the renewable resource, developing new energy and achieving the beneficial cycle of carbon in nature.
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Paragraph 0054; 0055; 0056

(2018/09/12)

Discovery and Structure-Based Optimization of Benzimidazole-Derived Activators of SOS1-Mediated Nucleotide Exchange on RAS
Son of sevenless homologue 1 (SOS1) is a guanine nucleotide exchange factor that catalyzes the exchange of GDP for GTP on RAS. In its active form, GTP-bound RAS is responsible for numerous critical cellular processes. Aberrant RAS activity is involved in ～30% of all human cancers; hence, SOS1 is an attractive therapeutic target for its role in modulating RAS activation. Here, we describe a new series of benzimidazole-derived SOS1 agonists. Using structure-guided design, we discovered small molecules that increase nucleotide exchange on RAS in vitro at submicromolar concentrations, bind to SOS1 with low double-digit nanomolar affinity, rapidly enhance cellular RAS-GTP levels, and invoke biphasic signaling changes in phosphorylation of ERK 1/2. These compounds represent the most potent series of SOS1 agonists reported to date.
Hodges, Timothy R.,Abbott, Jason R.,Little, Andrew J.,Sarkar, Dhruba,Salovich, James M.,Howes, Jennifer E.,Akan, Denis T.,Sai, Jiqing,Arnold, Allison L.,Browning, Carrie,Burns, Michael C.,Sobolik, Tammy,Sun, Qi,Beesetty, Yugandhar,Coker, Jesse A.,Scharn, Dirk,Stadtmueller, Heinz,Rossanese, Olivia W.,Phan, Jason,Waterson, Alex G.,McConnell, Darryl B.,Fesik, Stephen W.
p. 8875 - 8894
(2018/10/09)

Synthesis and characterization benzimidazole ring by using O-phenylinediamine with different compounds and using mannich reaction for preparation of some derivatives
The research includes synthesis and characterization Benzimidazole rings by using different compounds such as Urea, Thiourea and Carboxylic acid by reactant with O-phenylinediamine, then substitution hydrogen atom with present on nitrogen atom by reactant with primary and secondary amines according to Mannich reaction. Compounds was organized by using F.T.I.R and HNMR spectroscopy.
Kadhim, Abdullah Jawad
p. 473 - 481
(2018/03/21)

Stoichiometric Reactions of CO2 and Indium-Silylamides and Catalytic Synthesis of Ureas
The indium compounds In(N(SiMe3)2)2Cl?THF (2) and In(N(SiMe3)2)Cl2?(THF)n (3) were shown to react with CO2 to give [(Me3Si)2N)InX(μ-OSiMe3)]2 (X=N(SiMe3)2 4, Cl 5). 0.05–2.0 mol % of the species 3 acts as a pre-catalyst for the conversion of aryl and alkyl silylamines under CO2 (2–3 atm) to give the corresponding ureas in 70–99 % yields. A proposed mechanism is supported by experimental and computational data.
Xu, Maotong,Jupp, Andrew R.,Stephan, Douglas W.
supporting information
p. 14277 - 14281
(2017/10/31)

Sulfated polyborate-catalyzed efficient and expeditious synthesis of (un)symmetrical ureas and benzimidazolones
The excellent catalytic potential of sulfated polyborate is utilized in the synthesis of (un)symmetrical ureas and benzimidazolones by heating amines or substituted OPDA and urea or N-phenylureas under a solvent-free condition at 120 °C is described. The key advantages of the present protocol are phosgene-free, and other hazardous reagents or organic solvent free, high reaction rates and yields, simple workup procedure, and recyclability of the catalyst.
Rekunge, Deelip S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
supporting information
p. 4304 - 4307
(2017/10/12)

From Cells to Mice to Target: Characterization of NEU-1053 (SB-443342) and Its Analogues for Treatment of Human African Trypanosomiasis
Human African trypanosomiasis is a neglected tropical disease that is lethal if left untreated. Existing therapeutics have limited efficacy and severe associated toxicities. 2-(2-(((3-((1H-Benzo[d]imidazol-2-yl)amino)propyl)amino)methyl)-4,6-dichloro-1H-indol-1-yl)ethan-1-ol (NEU-1053) has recently been identified from a high-throughput screen of >42,000 compounds as a highly potent and fast-acting trypanocidal agent capable of curing a bloodstream infection of Trypanosoma brucei in mice. We have designed a library of analogues to probe the structure-activity relationship and improve the predicted central nervous system (CNS) exposure of NEU-1053. We report the activity of these inhibitors of T. brucei, the efficacy of NEU-1053 in a murine CNS model of infection, and identification of the target of NEU-1053 via X-ray crystallography.
Devine, William G.,Diaz-Gonzalez, Rosario,Ceballos-Perez, Gloria,Rojas, Domingo,Satoh, Takashi,Tear, Westley,Ranade, Ranae M.,Barros-álvarez, Ximena,Hol, Wim G. J.,Buckner, Frederick S.,Navarro, Miguel,Pollastri, Michael P.
p. 225 - 236
(2017/04/21)

Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene
A novel and efficient PhI(OAc)2-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF3·Et2O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials.
Zhang, Huaiyuan,Huang, Danfeng,Wang, Ke-Hu,Li, Jun,Su, Yingpeng,Hu, Yulai
p. 1600 - 1609
(2017/02/10)

Azole-Anion-Based Aprotic Ionic Liquids: Functional Solvents for Atmospheric CO2 Transformation into Various Heterocyclic Compounds
The chemical transformation of atmospheric CO2 is of great significance yet still poses a great challenge. Herein, azole-anion-based aprotic ionic liquids (ILs) were synthesized by the deprotonation of weak proton donors (e.g., 2-methylimidazole, 4-methylimidazole, and 2,4-dimethylimidazole) with tetrabutylphosphonium hydroxide, [Bu4P][OH]. We found that these ILs, such as [Bu4P][2-MIm], could activate atmospheric CO2 through the formation of carbamates. The resultant carbamate intermediates could further react with various types of substrate, including propargylic alcohols, 2-aminobenzonitriles, ortho-phenylenediamines, and 2-aminothiophenol, thereby producing α-alkylidene cyclic carbonates, quinazoline-2,4(1 H,3 H)-diones, benzimidazolones, and benzothiazoline, respectively, in moderate-to-good yields. Thus, we have achieved the transformation of CO2 at atmospheric pressure, and we expect this method to open up new routes for the synthesis of various oxygen-containing heterocyclic compounds under metal-free conditions.
Zhao, Yanfei,Wu, Yunyan,Yuan, Guangfeng,Hao, Leiduan,Gao, Xiang,Yang, Zhenzhen,Yu, Bo,Zhang, Hongye,Liu, Zhimin
p. 2735 - 2740
(2016/10/11)

Discovery of a Selective Aurora A Kinase Inhibitor by Virtual Screening
Here we report the discovery of a selective inhibitor of Aurora A, a key regulator of cell division and potential anticancer target. We used the atom category extended ligand overlap score (xLOS), a 3D ligand-based virtual screening method recently developed in our group, to select 437 shape and pharmacophore analogs of reference kinase inhibitors. Biochemical screening uncovered two inhibitor series with scaffolds unprecedented among kinase inhibitors. One of them was successfully optimized by structure-based design to a potent Aurora A inhibitor (IC50 = 2 nM) with very high kinome selectivity for Aurora kinases. This inhibitor locks Aurora A in an inactive conformation and disrupts binding to its activator protein TPX2, which impairs Aurora A localization at the mitotic spindle and induces cell division defects. This phenotype can be rescued by inhibitor-resistant Aurora A mutants. The inhibitor furthermore does not induce Aurora B specific effects in cells.
Kilchmann, Falco,Marcaida, Maria J.,Kotak, Sachin,Schick, Thomas,Boss, Silvan D.,Awale, Mahendra,G?nczy, Pierre,Reymond, Jean-Louis
p. 7188 - 7211
(2016/09/09)

HEPATITIS B VIRAL ASSEMBLY EFFECTORS
Novel assembly effector compounds having a therapeutic effect against hepatitis B viral (HBV) infection are disclosed. Assembly effector molecules described herein can lead to defective viral assembly and also may affect other viral activities associated with chronic HBV infection. Also disclosed is a process to synthesize disclosed compounds, method of treatment of HBV by administration of disclosed compounds, and use of these compounds in the manufacture of medicaments against HBV.
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Paragraph 00212

(2016/10/31)

Ball milling assisted solvent and catalyst free synthesis of benzimidazoles and their derivatives
Benzoic acid and o-phenylenediamine efficiently reacted under the green solvent-free Ball Milling method. Several reaction parameters were investigated such as rotation frequency; milling balls weight and milling time. The optimum reaction condition was milling with 56.6 g weight of balls at 20 Hz frequency for one hour milling time. The study was extended for synthesis of a series of benzimidazol-2-one or benzimidazol-2-thione using different aldehydes; carboxylic acids; urea; thiourea or ammonium thiocyanate with o-phenylenediamine. Moreover; the alkylation of benzimidazolone or benzimidazolthione using ethyl chloroacetate was also studied.
El-Sayed, Taghreed H.,Aboelnaga, Asmaa,Hagar, Mohamed
(2016/09/23)

An easy one-step synthesis of imidazolin-2-ones from phthalic anhydrides and their antioxidant evaluation
Treatment of phthalic anhydride derivatives with trimethylsilyl azide affords benzimidazolin-2-ones in 45-91% yield, which is the result of two consecutive Curtius reactions. Within the series obtained, 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one showed highest antioxidant activity.
López, Héctor S.,Enciso, José E.,Ochoa-Terán, Adrián,Velazquez, Juan I.,Sarmiento, Juan I.
p. 69 - 71
(2016/02/12)

Conjugates of degraded and oxidized hydroxyethyl starch and sulfonylureas: Synthesis, characterization, and in vivo antidiabetic activity
Orally administered drugs usually face the problem of low water solubility, low permeability, and less retention in bloodstream leading to unsatisfactory pharmacokinetic pro file of drugs. Polymer conjugation has attracted increasing interest in the pharmaceutical industry for delivering such low molecular weight (Mw) drugs as well as some complex compounds. In the present work, degraded and oxidized hydroxyethyl starch (HES), a highly biocompatible semisynthetic biopolymer, was used as a drug carrier to overcome the solubility and permeability problems. The HES was coupled with synthesized N-arylsulfonylbenzimidazolones, a class of sulfonylurea derivatives, by creating an amide linkage between the two species. The coupled products were characterized using GPC, FT-IR, 1H NMR, and 13C NMR spectroscopy. The experiments established the viability of covalent coupling between the biopolymer and N-arylsulfonylbenzimidazolones. The coupled products were screened for their in vivo antidiabetic potential on male albino rats. The coupling of sulfonylurea derivatives with HES resulted in a marked increase of the hypoglycemic activity of all the compounds. 2,3-Dihydro-3-(4-nitrobenzensulfonyl)-2-oxo-1H-benzimidazole coupled to HES10100 was found most potent with a 67% reduction in blood glucose level of the rats as compared to 41% reduction produced by tolbutamide and 38% by metformin. (Chemical Equation Presented).
Abbas, Muhammad Azhar,Hameed, Shahid,Farman, Muhammad,Kressler, J?rg,Mahmood, Nasir
p. 120 - 127
(2015/01/30)

Facile Synthesis of Benzo[ d ]azol-2(3 H)-ones Using 2-Phenoxycarbonyl-4,5-dichloropyridazin-3(2 H)-one as Green CO Source
Developing eco-friendly, stable, and easy-to-handle acyl sources is of great importance in synthetic and green chemistry. This study describes the synthesis of benzo[d]azol-2(3H)-ones such as benzo[d]thiazol-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, and benzo[d]imidazol-2(3H)-ones using 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one in one pot. The reaction reported is carried out under neutral or acidic conditions in the presence of zinc or sodium bicarbonate to give the corresponding heterocycles in good to excellent yields. The reaction uses a solid stable carbonyl source that is a recyclable functional-group carrier, pyridazin-3(2H)-one.
Ryu, Ki Eun,Kim, Bo Ram,Sung, Gi Hyeon,Yoon, Hyo Jae,Yoon, Yong-Jin
supporting information
p. 1985 - 1990
(2015/09/01)

Scope of chemical fixation of carbon dioxide catalyzed by a bifunctional monomeric tungstate
The tungsten-oxo moiety in a simple monomeric tungstate, TBA 2[WO4] (I, TBA = tetra-n-butylammonium), showed bifunctional activation of both CO2 and 1,2-phenylenediamine (1a). It was confirmed by 1H, 13C, and 183W NMR spectroscopies that adducts I-1a and I-(CO2)n (n = 1 and 2) were formed by the reactions of I with 1a and CO2, respectively. These adducts played important roles in formation of the corresponding carbamic acid intermediates. The present bifunctionality could be applied to chemical fixation of CO2 even at atmospheric pressure with various kinds of structurally diverse aryl diamines, primary monoamines, propargylic alcohols, and propargylic amines into cyclic urea derivatives, 1,3-disubstituted urea derivatives, cyclic carbonates, and cyclic carbamates, respectively.
Kamata, Keigo,Kimura, Toshihiro,Sunaba, Hanako,Mizuno, Noritaka
p. 160 - 166
(2014/03/21)

Lanthanide-catalyzed cyclocarbonylation and cyclothiocarbonylation: A facile synthesis of benzannulated 1,3-diheteroatom five- and six-membered heterocycles
La[N(SiMe3)2]3 proves to be an efficient catalyst system for the cyclocarbonylation of 1,2-disubstituted benzenes with isocyanates. In this approach, aryl/alkyl isocyanates react with o-phenylenediamine, o-aminophenol, o-aminothiophenol, catechols and anilines ortho-substituted by CH2NH2 and CONH2 to form, respectively, the corresponding benzimidazolones, benzoxazolones, benzothiazolones, benzodioxolones, 3,4-dihydroquinazolin-2(1H)-one, and quinazolinediones. These results represent the first example of lanthanide-catalyzed carbonylation. This methodology is also applicable for the preparation of various benzannulated 1,3-diheteroatom cyclic thioketones starting from aryl/alkyl isothiocyanates or CS2 in good to excellent yields. Based on the results of experiments performed using an o-aminobenzamido dianion lanthanide complex, a general mechanism, involving the tandem reaction of two lanthanide-ligand bonds with one heterocumulene molecule, is proposed as well.
Jing, Yufeng,Liu, Ruiting,Lin, Yanghui,Zhou, Xigeng
p. 1117 - 1125
(2014/08/18)

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs
A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.
Nakao, Syuhei,Mabuchi, Miyuki,Shimizu, Tadashi,Itoh, Yoshihiro,Takeuchi, Yuko,Ueda, Masahiro,Mizuno, Hiroaki,Shigi, Naoko,Ohshio, Ikumi,Jinguji, Kentaro,Ueda, Yuko,Yamamoto, Masatatsu,Furukawa, Tatsuhiko,Aoki, Shunji,Tsujikawa, Kazutake,Tanaka, Akito
supporting information
p. 1071 - 1074
(2014/03/21)

Benzoic acid-catalyzed transamidation reactions of carboxamides, phthalimide, ureas and thioamide with amines
An efficient and simple method for the transamidation of carboxamides, phthalimide, ureas and thioamide with amines catalyzed by commercially available benzoic acid under metal-free conditions is described. Furthermore, to the best of our knowledge, this is the first report about the transamidation of an aromatic thioamide with amines.
Wu, Ji-Wei,Wu, Ya-Dong,Dai, Jian-Jun,Xu, Hua-Jian
supporting information
p. 2429 - 2436
(2014/09/30)

DBU-based ionic-liquid-catalyzed carbonylation of o-phenylenediamines with CO2 to 2-benzimidazolones under solvent-free conditions
Herein, a new route was presented to synthesize 2-benzimidazolones via the carbonylation of o-phenylenediamines with CO2 catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-based ionic liquids under solvent-free conditions. DBU acetate ([DBUH][OAc]) displayed high efficiency for catalyzing the reactions of CO2 with o-phenylenediamines, and a series of benzimidazolones were obtained in high yields. It was demonstrated that [DBUH][OAc] could serve as a bifunctional catalyst for these reactions with the cation activating CO2 and the anion activating o-phenylenediamines. This protocol provides an effective and environmentally friendly alternative route for production of benzimidazolones, and extends the chemical utilization of CO2 in organic synthesis as well.
Yu, Bo,Zhang, Hongye,Zhao, Yanfei,Chen, Sha,Xu, Jilei,Hao, Leiduan,Liu, Zhimin
p. 2076 - 2082
(2013/09/24)

Cyclization of o-phenylenediamines by CO2 in the presence of H2 for the synthesis of benzimidazoles
The cyclization of o-phenylenediamines by CO2 in the presence of H2 was presented to directly synthesize benzimidazoles, and a series of benzimidazoles were obtained in excellent yields using RuCl 2(dppe)2 as the catalyst.
Yu, Bo,Zhang, Hongye,Zhao, Yanfei,Chen, Sha,Xu, Jilei,Huang, Changliang,Liu, Zhimin
supporting information
p. 95 - 99
(2013/02/25)

2+: A colorimetric molecular "light switch" and powerful stabilizer for G-quadruplex DNA
A new ruthenium complex, [Ru(bpy)2dppz-idzo]2+ (bpy = 2,2′-bipyridine, dppz-idzo = dipyrido-[3,2-a:2′,3′-c] phenazine-imidazolone), was synthesized and characterized. The luminescent titrations showed that the Ru-complex exhibited an outstanding "light switch" effect with an emission enhancement factor of about 300 in the presence of G-quadruplex DNA in a K+ solution. This remarkable "light switch" behavior can even be observed by the naked eye under irradiation with UV light. To get an insight into the "light switch" mechanism, quantum-chemical calculations were performed based on the DFT/TDDFT/PCM method at the B3LYP/6-31G* level. Furthermore, the CD titrations and thermal melting experiments indicated that [Ru(bpy) 2dppz-idzo]2+ could not only induce the formation of an antiparallel G-quadruplex structure in the absence of monocations, but also has the ability to stabilize the G-quadruplex architecture, implying potential applications in anticancer therapeutics. Both the "light switch" effect and the structure stabilization ability of [Ru(bpy)2dppz-idzo] 2+ were found to be superior to the well-known DNA molecular "light switch" [Ru(bpy)2dppz]2+. Finally, a "sandwich-like" binding model was proposed on the basis of molecular docking simulations.
Yao, Jun-Liang,Gao, Xing,Sun, Wenliang,Shi, Shuo,Yao, Tian-Ming
p. 5661 - 5672
(2013/06/05)

Cyclic thiourea/urea functionalized triphenylamine-based dyes for high-performance dye-sensitized solar cells
Six cyclic thiourea/urea functionalized triphenylamine-based dyes (AZ1-AZ6) containing 2-cyanoacrylic acid as an acceptor and various linkers (phenyl, biphenyl, and bithiophene) were synthesized. They exhibited high photovoltaic performance owing to an improved short-circuit photocurrent density (J sc) and open-circuit voltage (Voc). Among them, AZ6 bearing a cyclic thiourea group and bithiophene linker showed the highest power conversion efficiency (PCE) up to 7.29%, which was comparable to that of N719 (PCE = 7.36%).
Wu, Zhisheng,An, Zhongwei,Chen, Xinbing,Chen, Pei
supporting information
p. 1456 - 1459
(2013/07/05)

Synthesis, radical scavenging activity and structure-activity relationship of uric acid analogs
Uric acid (UA) is known to play an important role as an endogenous antioxidant. However, its insolubility in the serum is a risk for hyperuricemia. We assume that UA is an equivalent to hydroquinone or p-aminophenol, which can be oxidized to quinone/quinoimine and thus acts as a radical scavenger. Based on this hypothesis, a series of UA analogs was designed and synthesized. In the chemical radical scavenging assay, active compounds were considered as hydroquinone or p-aminophenol equivalents. A highly functionalized UA structure is not essential to have radical scavenging activity. Potent active 5-hydroxyindolinones (1a, 2a, and 3a) showed sufficient activity with high solubility and low cytotoxicity.
Yasuda, Daisuke,Takahashi, Kyoko,Kakinoki, Tomohiro,Tanaka, Yoko,Ohe, Tomoyuki,Nakamura, Shigeo,Mashino, Tadahiko
p. 527 - 529
(2013/06/04)

A green and simple synthesis of N-substituted-2-mercaptobenzimidazoles
A green and simple synthesis of N-alkyl-2-mercaptobenzimidazoles 5 (R= CH3, C2H5, CH2Ph) under, different conditions has been developed from N-alkyl-2-chlorobenzimidazole (i.e. CH 3, C2H5, CH2Ph) 4 by reaction with thiourea by physical grinding or by using green solvents like ethanol, PEG-600, etc. or by using micro-wave irradiation technique. Copyright
Rao, S Srinivas,Dubey,Kumari, Y Bharathi
p. 1210 - 1213
(2013/10/08)

Hydroxylamine as an oxygen nucleophile: Substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides
Benzothiazole-2-sulfonamides react with an excess of hydroxylamine in aqueous solutions to form 2-hydroxybenzothiazole, sulfur dioxide, and the corresponding amine. Mechanistic studies that employ a combination of structure-reactivity relationships, oxygen labeling experiments, and (in)direct detection of intermediates and products reveal that the reaction proceeds via oxygen attack, and that oxygen incorporated in the 2-hydroxybenzothiazole product derives from hydroxylamine. The reaction, which is performed under mild conditions, can be used as a deprotection method for cleavage of benzothiazole-2-sulfonyl-protected amino acids.
Kamps, Jos J. A. G.,Belle, Roman,Mecinovi?, Jasmin
p. 1103 - 1108
(2013/03/28)

Slow, spontaneous degradation of lansoprazole, omeprazole and pantoprazole tablets: Isolation and structural characterization of the toxic antioxidants 3H-benzimidazole-2-thiones
The spontaneous degradation of lansoprazole, omeprazole and pantoprazole tablets upon long-term and forced storage conditions was determined by high performance liquid chromatography (HPLC). The more abundant products could be isolated by liquid chromatography and their molecular weights determined by Mass Spectrometry (MS). Their structures, established according to their spectroscopic data, were compared to those of either the literature or of authentic samples. Thus lansoprazole led mainly to a mixture of 3H-benzimidazole-2-thione (2a) and 3H-benzimidazole-2-one (2c), omeprazole mainly to a mixture of 5-methoxy-3H-benzimidazole-2-thione (1a) and 2-hydroxymethyl-3, 5-dimethyl- 4-methoxypyridine (1b), and pantoprazole, to 5-difluoromethoxy-3H-benzimidazole-2-thione (3a) and 2-hydroxymethyl-3, 4-dimethoxypyridine (3b). Although some of the degradation products had already been observed under different conditions, the detection of benzimidazole-2- thiones is unprecedented and their involvement as possible physiological, yet toxic antioxidants must be emphasized. Plausible, unified mechanisms for the formation of the different degradation products observed herein and in previous papers from the literature are suggested.
Rajab,Touma,Rudler,Afonso,Seuleiman
p. 749 - 754
(2013/10/08)

A bifunctional tungstate catalyst for chemical fixation of CO2 at atmospheric pressure
No pressure: A simple monomeric tungstate, [WO4]2-, serves as a highly efficient homogeneous catalyst for various transformations of CO2 at atmospheric pressure. The tungsten-oxo moiety activates CO2 and the substrate simultaneously. The catalyst system is high yielding and applicable to a wide range of substrates such as amines (see scheme), 2-aminobenzonitriles, and propargylic alcohols. Copyright
Kimura, Toshihiro,Kamata, Keigo,Mizuno, Noritaka
supporting information; experimental part
p. 6700 - 6703
(2012/08/28)

Efficient copper(II)-catalyzed transamidation of non-activated primary carboxamides and ureas with amines
Amid(e) them all: Primary carboxamides and ureas react with aromatic and aliphatic amines in the presence of a copper catalyst to give a wide range of functionalized amides (see scheme). Copyright
Zhang, Min,Imm, Sebastian,Baehn, Sebastian,Neubert, Lorenz,Neumann, Helfried,Beller, Matthias
supporting information; experimental part
p. 3905 - 3909
(2012/06/04)

A practical one-step synthesis of 1,2-oxazoline derivatives from unprotected sugars and its application to chemoenzymatic β-N- acetylglucosaminidation of disialo-oligosaccharide
A facile and practical method for synthesis of sugar oxazolines (=dihydrooxazoles) from the corresponding N-acetyl-2-amino sugars has been developed by using 2-chloro-1,3-dimethyl-1H-benzimidazol-3-ium chloride (CDMBI) as a dehydrative condensing agent. The intramolecular dehydrative reaction between the 2-acetamido group and the anomeric OH group of unprotected N-acetyl-2-amino sugars took place smoothly in H2O, leading to the formation of a 1,2-oxazoline (=4,5-dihydrooxazole) moiety in good yield. Since the reaction proceeds in H2O without using any protecting groups, the resulting oxazolines can be utilized as effective glycosyl donors for the subsequent enzymatic glycosylation. We have successfully demonstrated a highly efficient chemoenzymatic transglycosylation of a disialo-oligosaccharide moiety to p-nitrophenyl N-acetylglucosaminide catalyzed by a mutant endo-N-acetylglucosaminidase without isolating disialo-oligosaccharide oxazoline as synthetic intermediate. Copyright
Noguchi, Masato,Fujieda, Tsukasa,Huang, Wei Chun,Ishihara, Masaki,Kobayashi, Atsushi,Shoda, Shin-Ichiro
p. 1928 - 1936
(2013/01/15)

Highly efficient synthesis of ureas and carbamates from amides by iodosylbenzene-induced hofmann rearrangement
A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method. A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. By using this method, heterocyclic products can be easily obtained in excellent yield. Ureidopeptides can also be prepared in good yield by this procedure. Copyright
Liu, Peng,Wang, Zhiming,Hu, Xianming
experimental part
p. 1994 - 2000
(2012/05/05)