# Sustainable Photocatalytic Synthesis of Glitazones via Riboflavin Tetraacetate

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

PMC · DOI: 10.1021/acs.joc.5c01306 · The Journal of Organic Chemistry · 2025-07-05

## TL;DR

A new sustainable method uses light and a vitamin derivative to make antidiabetic drugs more efficiently.

## Contribution

A novel photocatalytic method for synthesizing glitazones without transition metals is introduced.

## Key findings

- The method uses riboflavin tetraacetate to catalyze the coupling of thiazolidinediones with radical precursors.
- The process is transition-metal-free and works under mild conditions with various functional groups.
- The protocol was successfully used to prepare pioglitazone in three steps.

## Abstract

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-(CH2)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.

## Linked entities

- **Chemicals:** riboflavin tetraacetate (PubChem CID 9915369), pioglitazone (PubChem CID 4829)

## Full-text entities

- **Chemicals:** Glitazones (MESH:D045162), pioglitazone (MESH:D000077205), Riboflavin Tetraacetate (MESH:C058357), carboxylic acids (MESH:D002264), (Het)Ar-(CH2)n-thiazolidinediones (-), metal (MESH:D008670)

## Full text

_Full body text omitted from this summary view._ Fetch the complete paper as Markdown: https://tomesphere.com/paper/PMC12281567/full.md

## Figures

7 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12281567/full.md

## References

25 references — full list in the complete paper: https://tomesphere.com/paper/PMC12281567/full.md

---
Source: https://tomesphere.com/paper/PMC12281567