Base‐Mediated N‐Arylation for the Synthesis of 9H‐Pyrrolo[1,2‐a]indol‐9‐ones and 10H‐Indolo[1,2‐a]indol‐10‐ones

Abstract

Treatment of 2‐bromoaryl pyrrole/indol‐2‐yl ketones with cesium carbonate in DMF resulted in the formation of 9H‐pyrrolo[1,2‐a]indol‐9‐ones and 10H‐indolo[1,2‐a]indol‐10‐ones in moderate to excellent isolated yields.

Synthesis and Applications of 9H‐Pyrrolo[1,2‐a]indole and 9H‐Pyrrolo[1,2‐a]indol‐9‐one Derivatives

“…Recently, a transition metal‐free synthetic strategy was developed by Song (Scheme ) . Using (2‐bromophenyl)(1 H ‐pyrrol‐2‐yl)methanone substrates 145 , some flurazones 146 were isolated in moderate to excellent yields, with the use of cesium carbonate (11 examples, 46–98 % yield).…”

Copper-Catalyzed Synthesis of 3-Aryl-9H-imidazo[1,5-a]indol-9-ones Using Oxygen as the Sole Oxidant

“…Other frequently used practical methods include cyclocarbonylation and transition-metal-catalyzed intramolecular N -arylation . In recent years, fluorazone synthesis via intramolecular N -arylation of 2-bromoaryl pyrrole/indol-2-yl ketones under transition-metal-free conditions has also been realized . However, as compared the well-developed fluorazone synthesis, the development of the synthesis of 9 H -imidazo­[1,5- a ]­indol-9-ones in which an imidazole moiety is present is still in its infancy.…”