Highly Stereoselective Ugi/Pictet-Spengler Sequence

Discovering novel synthetic routes for rigid nitrogen-containing polyheterocycles using sustainable, atom-economical,and efficient (= short) synthetic pathways is of high interest in organic chemistry. Here, we describe an operationally simple andshort synthesis of the privileged scaffold dihydropyrrolo[1,2-a]pyrazine-dione from readily accessible starting materials. The alkaloid-type polycyclic scaffold with potential bioactivity was achieved by a multicomponent reaction (MCR)-based protocol via a Ugi four-component reaction and Pictet-Spengler sequence under different conditions, yielding a diverse library of products.

Automated summary

This paper describes a simple and short synthesis method for the privileged scaffold dihydropyrrolo[1,2-a]pyrazine-dione, a compound with potential bioactivity, using readily accessible starting materials and a multicomponent reaction-based protocol.