Details

Autor(en) / Beteiligte

• Zhou, Bigui
• Yuan, Zhiwei
• Yu, Jingxun
• Luan, Xinjun

Titel

Dearomatization/Deiodination of o‑Iodophenolic Compounds with α,β-Unsaturated Imines for Accessing Benzofuran Derivatives

Ist Teil von

• Organic letters, 2022-01, Vol.24 (3), p.837-841

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A dearomatization/deiodination/rearomatization strategy for the [3 + 2] cyclization of o-iodophenolic substrates with α,β-unsaturated imines to construct various dihydrobenzofuran-related skeletons has been established. Tolerance to different functional groups has been tested. Mechanistic studies revealed that this domino reaction was possibly realized by the deiodination and tautomerization of the key dearomatized intermediate to generate a free phenolic O radical. Moreover, an anticancer agent 4 and an α-glucosidase inhibitor 5 with high bioactivities were successfully synthesized using this novel protocol.