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

Authors
Quideau, SP Pouysegu, L Avellan, AV Whelligan, DK Looney, MA
Citation
Sp. Quideau et al., Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation, TETRAHEDR L, 42(42), 2001, pp. 7393-7396
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
42
Year of publication
2001
Pages
7393 - 7396
Database
ISI
SICI code
0040-4039(20011015)42:42<7393:HIOAO2>2.0.ZU;2-X
Abstract
Nitrogen-tethered 2-methoxyphenols are conveniently dearomatized into synth etically useful orthoquinol acetates by treatment with phenyliodine(III) di acetate in methylene chloride at low temperature. Subsequent fluoride- or b ase-induce intramolecular nucleophilic addition reactions furnish indole an d quinoline derivatives. The potential of this methodology for the synthesi s or a functionalized lycorine-type alkaloid skeleton is introduced here. ( C) 2001 Elsevier Science Ltd. All rights reserved.