59103-39-8

Upstream product

• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 100-44-7 benzyl chloride 
• 4981-92-4 1-benzylbenzimidazole 
• 36339-13-6 1,3-dibenzyl-1H-benzo[d]imidazol-3-ium chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 34840-27-2 2-[(Ethoxycarbonyl)amino]aniline 
• 28643-53-0 1,3-dihydro-1-(phenylmethyl)-2H-benzimidazol-2-one 
• 95-54-5 1,2-diamino-benzene 
• 108-88-3 toluene 

Relevant academic research and scientific papers

Iodine-catalyzed oxidative functionalization of purines with (thio)ethers or methylarenes for the synthesis of purin-8-one analogues

An efficient oxidative functionalization of purine-like substrates with (thio)ethers or methylarenes under mild conditions is described. Using I2as the catalyst, and TBHP as the oxidant, this protocol provides a valuable synthetic tool for the assembly of a wide range of 9-alkyl(benzyl)purin-8-one derivatives with high atom- and step-economy and exceptional functional group tolerance.

Mechanism studies of oxidation and hydrolysis of Cu(I)–NHC and Ag–NHC in solution under air

The decomposition of copper(I)–NHC and silver-NHC complexes in solution under air was studied. The Cu(I)–NHCs were oxidized into urea derivatives and hydrolysed into imidazoliums or benzimidazoliums. The decomposition of Ag–NHC with a saturated backbone led to ring-opening product, while the Ag–NHC with an unsaturated backbone led to imidazolium and Ag-bisNHC complex. The effects of steric property, hydrophilicity, and binding energy of NHC to O2 and H2O on the decomposition of Cu(I)–NHC were studied using theoretical calculations. Steric hindrance played an important role on the stability of Cu(I)–NHC. Pathways for the decomposition of Cu(I)–NHC and Ag–NHC were proposed.

Synthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air

A new synthetic method of urea derivatives using copper and air was developed. These mild conditions provided moderate to very good yields for 15 examples (53-93%), while low yields were obtained with sterically hindered substrates (3 examples). The reaction was found to go through an in situ generated copper-N-heterocyclic carbene, which was then oxidized into cyclic urea derivatives possessing alkyl, benzyl, aryl, hydroxy, Boc-protected, and tertiary amine groups.

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.

One-pot synthesis of 7,9-dialkylpurin-8-one analogues: Broad substrate scope

The one-pot and direct synthesis of 7,9-dialkylpurin-8-one analogues with broad substrate scope has been developed. This copper-catalyzed C-H oxidation reaction could avoid multistep synthesis of quaternary ammonium salts and expand the scope of halogenated alkanes. Moreover, benzimidazole derivatives are also applicable in the catalytic system.

NHCs-mediated benzoates formation directly from aromatic aldehydes and alkyl halides

A NHCs-mediated benzoates formation was developed by treatment of aromatic aldehydes with alkyl halides in the presence of oxygen. Corresponding benzoate derivatives were obtained in high yields up to 99%. The reaction mechanism was also discussed and a NHCs-mediated O-alkylation and subsequent oxidation process was proposed.

Synthesis of 2-imidazolones and 2-iminoimidazoles

Convenient methods for the direct conversion of imidazolium salts to the corresponding 2-imidazolone or 2-imino imidazole derivatives have been developed. Treatment of the salt with commercial bleach leads to effective oxidation at C2 and the formation of the corresponding imidazolone. Alternatively, treatment of the salt with an N-chloro amide affords the corresponding protected 2-amino derivative in good yield.

N-Bridged Heterocycles. Part 5. α,ω-Bis-(2-oxobenzimidazolinyl)-alkanes and -ethers as Selective Ligands for Group-1 and -2 Metals

A series of the title compounds (10), (12), and (13) and several analogues were synthesised from the readily available 1-isopropenylbenzimidazolin-2-one.Various substituents were attached to the unsubstituted nitrogen atoms of the benzimidazolinone moieties and the series of products obtained were tested for their complexing ability with group-1 and -2 metal-salts.The isolation of crystalline complexes, the solubilisation of the salts in chloroform by ligand, the i.r. carbonyl absorption shift, and the ion-transport ability of the ligand were examined as an index of complexation.Selective complexation, particularly for calcium, was noted in several cases.

Synthesis of 1-Alkyl and 1,3-Dialkyl-2-benzimidazolones from 1-Alkenyl-2-benzimidazolones using Phase-Transfer Catalysts Technique

A general synthetic route to 1-alkyl and 1,3-dialkyl-2-benzimidazolones from 1-alkenyl-2-benzimidazolenes using phase-transfer catalysis conditions is described.