Work

Sustainable Photocatalytic Synthesis of Glitazones via Riboflavin Tetraacetate

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A more sustainable and versatile method to access antidiabetic glitazones is demanded. Herein, we report the unprecedented photocatalytic coupling of N -protected methylene thiazolidinediones with radical precursors (organoborates or carboxylic acids) under riboflavin tetraacetate catalysis. The methodology accepts various functional groups and affords (Het)Ar-(CH 2 ) n -thiazolidinediones by transition-metal-free organic photoredox catalysis under mild conditions. The applicability of the developed protocol is showcased by the three-step preparation of the antidiabetic pioglitazone drug.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c01306

Authors: Sarah Jane Rezzi, Marco Koten, Rita Maria Concetta Di Martino, Gianluca Papeo, Tracey Pirali, Marina Caldarelli

Institutions: Università degli Studi del Piemonte Orientale “Amedeo Avogadro”, Nerviano Medical Sciences

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Associazione Italiana per la Ricerca sul Cancro, Ministero dell'Università e della Ricerca