85589-36-2

Usage

Uses

Used in Pharmaceutical Industry:
2-(2,2-diphenylcyclopropyl)-1H-imidazole is used as a metabolite in the context of Cibenzoline, an antiarrhythmic drug, for the treatment of cardiac arrhythmias. Its presence and study contribute to understanding the drug's metabolism and potential effects on the cardiovascular system.

InChI:InChI=1/C18H16N2/c1-3-7-14(8-4-1)18(15-9-5-2-6-10-15)13-16(18)17-19-11-12-20-17/h1-12,16H,13H2,(H,19,20)

Upstream product

• 53267-01-9 cifenline 

Relevant academic research and scientific papers

Novel process for the synthesis of class I antiarrhythmic agent (±)-cibenzoline and its analogs

Synthesis of (±)-cibenzoline and its analogs has been achieved by a simple sequence of reactions. The diaryl cyanoolefin intermediate 3 could be prepared by Knoevenagel condensation of benzophenone with ethylcyanoacetate to form the tetra-substituted olefin intermediate 2 followed by Krapcho deethoxycarbonylation or from β-hydroxynitrile intermediate 2' followed by the elimination of hydroxyl group respectively. The 2,2- diphenylcyclopropanecarbonitrile 4 was synthesized from intermediate 3 by cyclopropanation, which was converted to (±)-2-(2,2-diphenylcyclopropyl)- 2-imidazoline 5 by reaction with ethylenediamine in the presence of a catalytic amount of sulfur. Moreover, the obtained 2-imidazolines were smoothly oxidized to the corresponding imidazoles 6 in good to moderate yields. Copyright Taylor & Francis Group, LLC.