Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation

✍ Scribed by Stéphane Quideau; Laurent Pouységu; Anne-Virginie Avellan; Daniel K Whelligan; Matthew A Looney

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 100 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01514-3

✦ Synopsis

Nitrogen-tethered 2-methoxyphenols are conveniently dearomatized into synthetically useful orthoquinol acetates by treatment with phenyliodine(III) diacetate in methylene chloride at low temperature. Subsequent fluoride-or base-induced intramolecular nucleophilic addition reactions furnish indole and quinoline derivatives. The potential of this methodology for the synthesis of a functionalized lycorine-type alkaloid skeleton is introduced here.