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.
Author details: | Bernd SchmidtORCiDGND, Martin Riemer, Uwe SchildeORCiDGND |
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DOI: | https://doi.org/10.1002/ejoc.201501151 |
ISSN: | 1434-193X |
ISSN: | 1099-0690 |
Title of parent work (English): | European journal of organic chemistry |
Publisher: | Wiley-VCH |
Place of publishing: | Weinheim |
Publication type: | Article |
Language: | English |
Year of first publication: | 2015 |
Publication year: | 2015 |
Release date: | 2017/03/27 |
Tag: | Allylic compounds; Arenes; Michael addition; Microwave chemistry; Oxygen heterocycles; Rearrangement |
Issue: | 34 |
Number of pages: | 10 |
First page: | 7602 |
Last Page: | 7611 |
Funding institution: | equal opportunities fund of the faculty of science |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
Peer review: | Referiert |