Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow

• DOI: 10.1021/acs.orglett.8b03392
• Publication Date: 2018-11-27T13:00:48Z
• Authors: Johannes Schwan; Merlin Kleoff; Bence Hartmayer; Philipp Heretsch; Mathias Christmann
• Keywords: Aryne; Reaction conditions

A general strategy for the synthesis of 3,4-dioxygenated quinolin-2-one natural products is reported. The key step a regioselective insertion arynes into unsymmetric imides. When performed in continuous flow, reaction proceeds within minutes, while lower yields and longer times are observed batch. resulting N-acylated 2-aminobenzophenones were transformed to (±)-peniprequinolone, (±)-aflaquinolones E F, (±)-6-deoxyaflaquinolone E, (±)-quinolinones B, (±)-aniduquinolone C 1-3 steps.