Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives

Abstract

A novel and efficient synthesis of N-substituted dipyrrolo[1,2-a:2',1'-c]pyrazine derivatives has been developed. The synthetic strategy relies on the synthesisof 4',5'-dihydro-1H,3'H-2,2'-bipyrrole, followed by the reaction with propargyl bromide. Various substituents were introduced to the alkyne functionality using the Sonogashira coupling reaction. Aromatization of the dihydropyrrole ring followed by an intramolecular cyclization reaction between the alkyne functionality and the pyrrole nitrogen atom was catalyzed by Pd/C at high temperature to furnish the desired dipyrrolo-pyrazine skeleton. (C) 2019 Elsevier Ltd.