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Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones

  • Allyl, dimethylallyl and prenyl ethers derived from o-acyl-phenols 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.

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Author:Bernd SchmidtORCiDGND, Martin Riemer, Uwe SchildeORCiDGND
ISSN:1434-193X (print)
ISSN:1099-0690 (online)
Parent Title (English):European journal of organic chemistry
Place of publication:Weinheim
Document Type:Article
Year of first Publication:2015
Year of Completion:2015
Release Date:2017/03/27
Tag:Allylic compounds; Arenes; Michael addition; Microwave chemistry; Oxygen heterocycles; Rearrangement
First Page:7602
Last Page:7611
Funder:equal opportunities fund of the faculty of science
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert