Synthesis of non-anomeric C-glycosyl pyrazolidinone derivatives via visible-light photoredox catalysis

Author(s)

Goncalves, Renan. O. ; Oliveira, Pedro H. R. ; de Jesus, Iva S. ; Debia, Natali P. ; Ludtke, Diogo S. ; Paixao, Marcio W.

• Document type: Journal article
• Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 21, n. 27, p. 5-pg., 2023-06-14.

Abstract

C-Glycosyl compounds have gained considerable attention over the last few decades due to their high chemical stability and promising applications in drug discovery. Herein we disclose an operationally simple, metal-free, photocatalytic approach for the glycosylation of azomethine imines using 4-glycosyl-1,4-dihydropyridines (DHPs) as radical precursors. The protocol features mild reaction conditions, scalability, broad substrate scope, and good functional group tolerance. Moreover, the resulting pyrazolidinone moiety can be easily deprotected, acylated or reduced into a glycosyl & beta;-alanine analog. (AU)

• FAPESP's process: 21/06099-5 - Development of new photochemical methodologies for the synthesis of small molecule and biomolecule modifications
• Grantee: Márcio Weber Paixão
• Support Opportunities: Regular Research Grants