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.
Sustainable Photocatalytic Synthesis of Glitazones via Riboflavin Tetraacetate
Rezzi, Sarah JanePrimo
;Koten, Marco;Di Martino, Rita Maria Concetta;Pirali, Tracey
;
2025-01-01
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.File in questo prodotto:
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