Premium
Tandem Claisen Rearrangement/6‐ endo Cyclization Approach to Allylated and Prenylated Chromones
Author(s) -
Schmidt Bernd,
Riemer Martin,
Schilde Uwe
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501151
Subject(s) - chemistry , chromone , claisen rearrangement , tandem , prenylation , cope rearrangement , stereochemistry , microwave irradiation , sequence (biology) , organic chemistry , catalysis , enzyme , biochemistry , materials science , composite material
Allyl, dimethylallyl and prenyl ethers derived from o ‐acylphenols reacted upon microwave irradiation to form C ‐allylated or ‐prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6‐ endo ‐ trig or 6‐ endo ‐ dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6‐prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.