1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1<i>H</i>-benzo [<i>d</i>] imidazole-2-amine

Abstract

The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and 13C-NMR spectroscopy.

Keywords

• natural products
• synthesis
• NMR spectroscopy
• condensation
• 2-aminoimidazole