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Photoredox-Catalyzed Radical Cascade Cyclization of N -Cyanamide Alkenes with N -Aminopyridinium Salts: Modular Synthesis of Polycyclic Quinazolinones

2025/11/04 by Zhiwei Xu, Yuting Leng, Mengda Song +2 · 3 citations
Chemistry · #Cascade #Cascade reaction #Catalytic C–H Functionalization Methods #Dual (grammatical number) #Modular design #Quinazolinone synthesis and applications #Radical Photochemical Reactions #Radical cyclization #Substrate (aquarium)

paper · doi:10.1021/acs.joc.5c02191

published in The Journal of Organic Chemistry 90(45), 16169-16174 (American Chemical Society)

openalex publication_date 2025/11/04 · openalex created_date 2025/11/05 · openalex updated_date 2026/08/06

Abstract

A photoredox-catalyzed strategy enables the dual N-centered radical cascade cyclization of N -cyanamide olefins with N -sulfon/benzoylaminopyridinium salts, efficiently constructing 48 amide-decorated 2,3-fused polycyclic quinazolinones in yields of up to 86%. This metal- and base-free protocol exhibits mild reaction conditions. Moreover, they are compatible with a variety of functional groups and can accommodate a range of substrate structures. Notably, the method’s practical utility is highlighted by successful gram-scale implementation and facile downstream derivatization.

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