14813-85-5

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenyl-2,3-dihydro-1H-benzimidazole-2-one is used as a pharmaceutical agent for its potential anti-inflammatory properties, offering a new avenue for the treatment of inflammatory conditions by modulating the body's inflammatory response.
Used in Oncology:
In the field of oncology, PDBI is utilized as an anti-cancer agent, targeting various types of cancer cells. Its mechanism of action may involve the inhibition of cell proliferation and induction of apoptosis, making it a promising candidate for further research and development in cancer therapy.
Used in Microbiology:
1-Phenyl-2,3-dihydro-1H-benzimidazole-2-one is employed as an anti-microbial agent, effective against a range of microorganisms. Its potential use in combating bacterial and fungal infections highlights its versatility in the medical field.
Used in Drug Design and Development:
PDBI is used as a structural template in drug design and development due to its unique chemical properties and pharmacological effects. Its potential to be modified and optimized for specific therapeutic applications makes it a valuable asset in the creation of new drugs.

InChI:InChI=1/C13H10N2O/c16-13-14-11-8-4-5-9-12(11)15(13)10-6-2-1-3-7-10/h1-9H,(H,14,16)

Upstream product

• 100394-65-8 (2-anilino-phenyl)-urea 
• 102-07-8 bis(diphenyl)urea 
• 75-44-5 phosgene 
• 534-85-0 N-phenyl-1,2-benzenediamine 
• 79759-13-0 (2-Phenylamino-phenyl)-carbamic acid ethyl ester 
• 78162-51-3 1-(N-tert-Butylformimidoyl)-3-phenyl-2-benzimidazolinon 
• 67-66-3 chloroform 
• 1227476-15-4 Azobenzene 
• 86465-40-9 1-methoxy-3-phenyl-2-benzimidazolinone 
• 13114-91-5 1-(2-bromophenyl)-3-phenylurea 
• 622-44-6 phenylcarbonimidic dichloride 
• 95926-77-5 1-(2-Cyclohexen-1-yl)-1,4-dihydro-4-phenyl-5H-tetrazol-5-on 
• 1148017-10-0 C₁₈H₁₈N₂O₃ 
• 862891-89-2 1-benzyl-1-(2-chlorophenyl)-3-phenylurea 

Downstream Products

• 78162-50-2 1-Acetyl-3-phenyl-2-benzimidazolinon 
• 125030-82-2 1,3-dihydro-1-phenyl 3-(2-propynyl)-2H-benzimidazol-2-one 
• 23996-36-3 1-methyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 24547-45-3 2-chloro-1-phenyl-1H-benzo[d]imidazole 
• 79759-86-7 1-Methyl-3-phenyl-1,3-dihydro-benzoimidazole-2-thione 
• 83421-92-5 7-(2-oxo-3-phenyl-benzimidazolin-1-yl)-enanthic acid ethyl ester 
• 1148017-15-5 C₁₅H₁₃BrN₂O 
• 938470-08-7 C₄₁H₂₇N₇O₂ 
• 938469-99-9 C₄₅H₃₀N₆O₃ 

Relevant academic research and scientific papers

Direct Synthesis of N-Monosubstituted Benzimidazol-2-ones via Ph 3P-I 2-Mediated Reaction of Hydroxamic Acids

A facile approach for the synthesis of benzimidazolones via a Ph3P-I2 promoted reaction of hydroxamic acids is reported. Upon Lossen-type rearrangement of the O-activated hydroxamic acids, the in situ generated isocyanates undergo an intramolecular attack by ortho N-nucleophiles producing the cyclized products in good yields under mild conditions. The method allows the direct preparation of a single regioisomer of N-monosubstituted derivatives using readily accessible starting materials and low-cost reagents with broad substrate scope.

Benzimidazolone derivatives organic light emitting compound and organic electroluminescent device including the same

Provided is a benzo imidazolone derivative organic electroluminescent compound represented by chemical formula a. Chemical Formula a. The benzo imidazolone derivative organic light emitting compound is suitable for inclusion in an organic electroluminescent device. Both electrochemical stability and thermal stability can be satisfactorily met.

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.

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.

Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system

A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.

Chemoselective: N -arylation of aminobenzamides via copper catalysed Chan-Evans-Lam reactions

Chemoselective N-arylation of unprotected aminobenzamides was achieved via Cu-catalysed Chan-Evans-Lam cross-coupling with aryl boronic acids for the first time. Simple copper catalysts enable the selective arylation of amino groups in ortho/meta/para-aminobenzamides under open-flask conditions. The reactions were scalable and compatible with a wide range of functional groups.

Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates

A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.

Aryliminophosphoranes as Key Intermediates in the One-Pot Synthesis of 1-Aryl-1,3-dihydro-2H-benzimidazol-2-ones from N-Aryl-2-nitrosoanilines and Carbon Dioxide under Mild Metal-Free Conditions

A new and convenient protocol is presented for the synthesis of 1-arylbenzimidazol-2-ones by a one-pot reaction of N-aryl-2-nitrosoanilines using solid carbon dioxide as a source of the key carbonyl moiety. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The atom economy of the synthesis of the starting nitrosoanilines, accomplished by substitution of hydrogen, makes the entire synthesis of the target compounds environmentally friendly.

Synthesis and in silico evaluation of novel compounds for PET-based investigations of the norepinephrine transporter

Since the norepinephrine transporter (NET) is involved in a variety of diseases, the investigation of underlying dysregulation-mechanisms of the norepinephrine (NE) system is of major interest. Based on the previously described highly potent and selective NET ligand 1-(3-(methylamino)-1-phenylpropyl)-3-phenyl-1,3-dihydro-2H-benzimidaz- ol-2-one (Me@APPI), this paper aims at the development of several fluorinated methylaminebased analogs of this compound. The newly synthesized compounds were computationally evaluated for their interactions with the monoamine transporters and represent reference compounds for PET-based investigation of the NET.

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.