Rearrangement of 5-O-prenyl flavones: a regioselective access to 6-C-(1,1-dimethylallyl)- and 8-C-(3,3-dimethylallyl)-flavones

Authors
Daskiewicz, JB Bayet, C Barron, D
Citation
Jb. Daskiewicz et al., Rearrangement of 5-O-prenyl flavones: a regioselective access to 6-C-(1,1-dimethylallyl)- and 8-C-(3,3-dimethylallyl)-flavones, TETRAHEDR L, 42(41), 2001, pp. 7241-7244
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
41
Year of publication
2001
Pages
7241 - 7244
Database
ISI
SICI code
0040-4039(20011008)42:41<7241:RO5FAR>2.0.ZU;2-Z
Abstract
Regioselective control of the Claisen rearrangement of 7-MEM-5-prenyl chrys in was achieved by microwave irradiation. The nature of the products was in fluenced by the irradiation power and the type of solvent. Irradiation at 7 50 W in N,N-diethylaniline specifically yielded the 8-(3,3-dimethylallyl) p ara-rearranged product while refluxing in N,N-diethylbutylamine gave select ive access to the 6-(1,1-dimethylallyl) ortho-rearranged compound. (C) 2001 Elsevier Science Ltd. All rights reserved.