Synthesis of 2-Heptyl-1-hydroxy-4(1H)-quinolone - Unexpected Rearrangement of 4-(Alkoxycarbonyloxy)quinoline N-Oxides to 1-(Alkoxycarbonyloxy)-4(1H)-quinolones

Anna Woschek; Marek Mahout; Kurt Mereiter; Friedrich Hammerschmidt

doi:10.1055/s-2007-966020

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Synthesis of 2-Heptyl-1-hydroxy-4(1H)-quinolone - Unexpected Rearrangement of 4-(Alkoxycarbonyloxy)quinoline N-Oxides to 1-(Alkoxycarbonyloxy)-4(1H)-quinolones

Anna Woschek^a, Marek Mahout^a, Kurt Mereiter^b, Friedrich Hammerschmidt*^a
^a Institut für Organische Chemie, Universität Wien, Währingerstraße 38, 1090 Vienna, Austria
Fax: +43(1)427795231; e-Mail: friedrich.hammerschmidt@univie.ac.at;
^b Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, 1060 Vienna, Austria

Abstract

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Abstract

2-Heptyl-4(1H)-quinolone was converted in two steps into the 4-ethoxycarbonyloxy-, 4-(tert-butoxycarbonyloxy)-, and 4-(dimethylaminocarbonyloxy)quinoline N-oxides. While the former two rearranged to the corresponding 1-(alkoxycarbonyloxy)-4(1H)-quinolones at room temperature, the latter was stable, even at 140 °C in refluxing xylenes. Basic hydrolysis of these compounds furnished 2-heptyl-1-hydroxy-4(1H)-quinolone.

Key words

acylations - heterocycles - quinolines - rearrangements - oxidations

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CCDC 616835-616836 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data.requecst/cif.