46818-46-6

Upstream product

• 1632-83-3 1-Methylbenzimidazole 
• 882-33-7 diphenyldisulfane 
• 591-50-4 iodobenzene 
• 2360-22-7 1-methyl-1H-benzimidazole-2-thiol 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 108-98-5 thiophenol 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 

Downstream Products

• 33158-52-0 1-benzyl-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 1849-01-0 1-methyl-2-benzimidazolone 

Relevant academic research and scientific papers

Lewis acid / Base-free Strategy for the Synthesis of 2-Arylthio and Selenyl Benzothiazole / Thiazole and Imidazole

A Cu(II)-catalyzed Csp2-Se and Csp2-Sulfur bond formation was achieved with moderate to good yields without the aid of Lewis acid and base. The reaction is compatible with a wide range of heterocycles such as benzothiazole, thiazole, and imidazole. Also, this typical protocol is found to be active in thio-selenation via S-H activation. Additionally, we proposed a plausible mechanistic pathway involving Cu(III) putative intermediate.

Ligand-Free CuI-Catalyzed Chemoselective S-Arylation of 2-Mercaptobenzimidazole with Aryl Iodides

A practical and efficient strategy for the chemoselective C-S cross-coupling of 2-mercaptobenzimidazole derivatives with a range of substituted aryl iodides is described. Under the optimized conditions of 5 mol% CuI and 100 °C, a variety of S-arylated products were obtained in good to excellent yields (up to 92 %) without the need for assisting ligands.

Aromatic homolytic substitution using solid phase synthesis

Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.

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.