2-Alkoxyarenol-derived orthoquinols in carbon-oxygen, carbon-nitrogen and carbon-carbon bond-forming reactions

Authors
Quideau, S Pouysegu, L Oxoby, M Looney, MA
Citation
S. Quideau et al., 2-Alkoxyarenol-derived orthoquinols in carbon-oxygen, carbon-nitrogen and carbon-carbon bond-forming reactions, TETRAHEDRON, 57(2), 2001, pp. 319-329
Citations number
74
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
2
Year of publication
2001
Pages
319 - 329
Database
ISI
SICI code
0040-4020(20010107)57:2<319:2OICCA>2.0.ZU;2-R
Abstract
Silylated oxygen- and nitrogen-tethered orthoquinol acetates, generated by phenyliodine(III) diacetoxy-mediated oxidative acetoxylation of 2-alkoxyphe nols in CH2Cl2 can be used to furnish regioselectively benzannulated hetero cycles. Oxidative activation of 2-alkoxynaphthols with non-nucleophilic phe nyliodine(III) bis(trifluoroacetoxy) in the presence of carbon nucleophiles , including oxidation sensitive silyl enol ethers, constitute a potentially valuable route to naturally occurring vicinally oxygenated benz[a]anthrace ne motifs. (C) 2000 Elsevier Science Ltd. All rights reserved.