A new method for the synthesis of highly substituted pyrroles and application to the synthesis of fluorescing dyes and expanded porphyrins

Pyrroles are nitrogen containing heterocyclic compounds that are applied in medicinal and material chemistry. Progress in this area of research is hampered by the complicated synthetic pathways that often are needed to obtain these heterocycles. In this project, we aim to devise an effective and high yielding synthesis of substituted pyrroles from readily available starting materials such as enolizable ketones and 2-aminoalcohols. The reaction will not involve expensive or toxic catalysts or reagents and be generallly applicable, for instance to bioactive natural products, affording libraries of novel compounds that can be tested for their biological activities. Another application is in the conversion of these alfa-unsubstituted pyrroles to highly fluorescent BODIPY and BOPHY dyes, or in the synthesis of unique expanded porphyrins that are difficult or impractical to prepare using the classical pathways.

Keywords:expanded porphyrins, multicomponent reactions, fluorescent dyes, pyrroles, synthetic methodology

Disciplines:(Bio)molecular modelling and design