Hypervalent iodine(III)-induced intramolecular cyclization of alpha-(aryl)alkyl-beta-dicarbonyl compounds: A convenient synthesis of benzannulated and spirobenzannulated compounds

Authors
Arisawa, M Ramesh, NG Nakajima, M Tohma, H Kita, Y
Citation
M. Arisawa et al., Hypervalent iodine(III)-induced intramolecular cyclization of alpha-(aryl)alkyl-beta-dicarbonyl compounds: A convenient synthesis of benzannulated and spirobenzannulated compounds, J ORG CHEM, 66(1), 2001, pp. 59-65
Citations number
63
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
1
Year of publication
2001
Pages
59 - 65
Database
ISI
SICI code
0022-3263(20010112)66:1<59:HIICOA>2.0.ZU;2-A
Abstract
A novel hypervalent iodine(III)-induced direct intramolecular cyclization o f alpha-(aryl)alkyl-beta -dicarbonyl compounds has been described. Both met a-and para-substituted phenol ether derivatives containing acyclic or cycli c 1,3-dicarbonyl moieties at the side chain undergo this reaction in a faci le manner. The reactions afford benzannulated and spirobenzannulated compou nds that are of biological importance. The reaction is found to be general, mild,: and high yielding. The mechanism: of the reaction has been shown to involve a cation radical intermediate.