Modification of Pyrrolo[2,1-a]isoquinolines and Polysubstituted Pyrroles via Methylenation with Acetyl Chloride and Dimethylsulfoxide

A convenient synthesis of methylene-bridged pyrrolo[2,1-a]isoquinolines has been developed. Treatment of pyrroloisoquinolines with acetyl chloride and dimethylsulfoxide (DMSO) at ambient temperature afforded bispyrroloisoquinolylmethanes in 17-85% yields. This reaction system can also be expanded to the synthesis of bispyrrolylmethanes (34-94% yields). Easy chemical transformation of methylene-bridged pyrroloisoquinoline provided an unsymmetric acid and amide possessing a privileged framework.

Automated summary

A convenient synthesis method for methylene-bridged pyrrolo[2,1-a]isoquinolines has been developed, yielding bispyrroloisoquinolylmethanes and bispyrrolylmethanes in good yields. This synthesis method also allows for easy chemical transformation of the methylene-bridged pyrroloisoquinoline, providing unsymmetric acids and amides with a privileged framework.