Synthesis of Allyl- and Prenylcoumarins via Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination

2015/10/20 by Bernd Schmidt, Martin Riemer
Agricultural and Biological Sciences · Medicine · #Fungal Plant Pathogen Control #Plant chemical constituents analysis #Synthesis of Organic Compounds

paper · doi:10.1055/s-0035-1560501

Abstract

Allyl, dimethylallyl, crotyl, and prenyl ethers of various aromatic <i>ortho</i>-hydroxy carbonyl compounds undergo a tandem sequence of Claisen rearrangement, carbonyl olefination, and cyclization upon microwave irradiation in the presence of a stabilized ylide. The products are multiply substituted 6- or 8-allylated or prenylated coumarins (2<i>H</i>-chromen-2-ones).

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