Rhodium-Catalyzed Direct Arylation of Furopyridine: Synthesis and the Cardiac Effects of Dictamnine Derivatives

Herein is reported a Rh-2(OAc)(4)/IMes . HCl system that promotes the chemoselective installation of aryl groups at the 2-position of furo[2,3-b]pyridine (53-94% yields). The method is applicable to the direct modification of the natural furoquinoline alkaloid dictamnine. The cardiac effects of the fluorinated analogues improved, compared to dictamnine at 160 mu g/mL. Preliminary mechanism of action studies indicate that the effects might be related to epinephrine alpha receptors, M-receptor, and calcium channel receptor.

Automated summary

A Rh-2(OAc)(4)/IMes . HCl system is reported in this study, which enables the chemoselective installation of aryl groups at the 2-position of furo[2,3-b]pyridine with yields ranging from 53% to 94%. The modified furoquinoline alkaloid dictamnine shows improved cardiac effects compared to the natural compound, possibly through interactions with epinephrine alpha receptors, M-receptors, and calcium channel receptors.