Synthesis, Table of Contents Synthesis 2016; 48(01): 141-149DOI: 10.1055/s-0035-1560501 paper © Georg Thieme Verlag Stuttgart · New YorkSynthesis of Allyl- and Prenylcoumarins via Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination Authors Author Affiliations Bernd Schmidt* Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany Email: bernd.schmidt@uni-potsdam.de Martin Riemer Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam-Golm, Germany Email: bernd.schmidt@uni-potsdam.de Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract Allyl, dimethylallyl, crotyl, and prenyl ethers of various aromatic ortho-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 (2H-chromen-2-ones). Key words Key wordsaldehydes - coumarins - ketones - microwave irradiation - olefination - tandem reaction - ylides Full Text References References 1 Schmidt B, Riemer M, Schilde U. Synlett 2014; 25: 2943 2 Schmidt, B.; Riemer, M.; Schilde, U. Eur. J. Org. Chem. 2015, in press. 3 Cairns N, Harwood LM, Astles DP. J. Chem. Soc., Chem. Commun. 1986; 1264 4 Cairns N, Harwood LM, Astles DP. J. Chem. Soc., Perkin Trans. 1 1994; 3101 5 Mali RS, Sandhu PK, Manekar-Tilve A. J. Chem. Soc., Chem. Commun. 1994; 251 6 Mali RS, Sandhu PK. Synth. Commun. 1994; 24: 2883 7 Mali RS, Joshi PP. Synth. Commun. 2001; 31: 2753 8 Mali RS, Joshi PP, Sandhu PK, Manekar-Tilve A. J. Chem. Soc., Perkin Trans. 1 2002; 371 9 Boeck F, Blazejak M, Anneser MR, Hintermann L. Beilstein J. Org. Chem. 2012; 8: 1630 10 Guz NR, Lorenz P, Stermitz FR. 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Res. 2011; 26: 2107 Supplementary Material Supplementary Material Supporting Information (PDF)
