33158-52-0

Upstream product

• 1632-83-3 1-Methylbenzimidazole 
• 108-88-3 toluene 
• 620-05-3 iodomethylbenzene 
• 4981-92-4 1-benzylbenzimidazole 
• 74-88-4 methyl iodide 
• 56463-13-9 1-benzyl-3-methyl-1H-benzimidazol-3-ium iodide 
• 46818-46-6 1-methyl-1H-benzo[d]imidazol-2-yl phenyl sulfide 

Downstream Products

• 1849-01-0 1-methyl-2-benzimidazolone 

Relevant academic research and scientific papers

TEMPO-Mediated Synthesis of N-(Fluoroalkyl)imidazolones via Reaction of Imidazoles with Iodofluoroacetate

We report a TEMPO-mediated oxidative copper-catalyzed synthesis of N-(fluoroalkyl)imidazolones via the radical addition of imidazoles with iodofluoroacetate. A possible key intermediate involving TEMPO was observed by ESI-MS. We also found that aerobic ox

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.

Metal-free C(sp2)-H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination

The direct C2-H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2-H oxidation, imination, and amination of azoles. Significantly, these reactions proceed under mild conditions with high to excellent yields, are scalable to large quantity and exhibit a broad substrate scope. Interestingly, this direct C2-H imination method allowed us to access various pharmacologically active N6-alkyl or N6-aryl substituted benzimidazoquinazolinone scaffolds through intramolecular C-H imination in a sequential one-pot reaction.

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.

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.

Synthesis of a regio-isomer of kealiiquinone, a marine benzimidazole alkaloid

Treatment of 1,3-dialkyl-2-(phenylthio)benzimidazolium salts 3 and 1,3-dialkyl-2-phenylthio-1H-imidazolium salts 7 with aq. K2CO3 gives 1,3-dialky1-1,3-dihydrobenzimidazol-2-ones 4 and 1,3-dialkyl-1,3-dihydroimidazol-2-ones 8, respectively, in 22-94% yield. A regio-isomer 17 of kealiiquinone, a marine benzimidazole alkaloid, where the 4-methoxyphenyl group at the 4-position migrates to the 9-position, is synthesized by application of the reaction. Cytotoxity of 17 and kealiiquinone against 39 human cancer cells is evaluated. They have weak activity but a unique mechanism of action.