DDQ-promoted synthesis of 2-benzoylbenzofurans and benzofuro[2,3- c ]pyridines using 2′-hydroxy ethyl cinnamate and phenacyl bromides
Abstract
]pyridines from 2'-hydroxyethyl cinnamate and phenacyl bromides. Mechanistic studies indicate that the CN radical, generated through the homolytic cleavage of the C-C bond of DDQ, served as a key intermediate in the reaction. DDQ-mediated single-electron transfer initiates the cascade process of radical addition, and 1-2 addition of DDQ promotes cyclization. A wide range of bicyclic and tricyclic ring systems of benzofuran and benzofuropyridine are obtained in this methodology with moderate to good yields. This transformation features a broad substrate scope, operates under organometallic catalyst-free conditions, utilises readily accessible starting materials, and demonstrates potential for scale-up. Additionally, it allows for the simultaneous formation of two new C-C and C-N bonds in a single operation.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Synthesis and bioactivity of alkaloids
Synthesis of Organic Compounds
Publication details
- Journal / source
- RSC Advances
- Publisher
- Royal Society of Chemistry (RSC)
- Volume
- 16
- Issue
- 4
- Pages
- 3129–3137
- Publication date
- 1 January 2026
- Language
- EN