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Oxydehydrogenative aromatization of fused 3-aminopyran-2-ones on carbon surfaces: a simple approach towards 3-amino-5-hydroxycoumarin derivatives

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Abstract

Aromatization of selected 3-acylamino-5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones, yielding the corresponding 3-acylamino-5-hydroxycoumarins, was achieved by dehydrogenation with molecular oxygen in the presence of activated carbon. The use of nonpolar solvents and high temperatures was crucial for attaining satisfactory conversions. The 3-benzoylamino-5,6,7,8-tetrahydrocoumarin without a 5-keto group and the 8-oxo analogue as well as the 5-oxo-5,6,7,8-tetrahydrocoumarins containing a free 3-amino group were less efficiently aromatized.

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Acknowledgments

We thank the Ministry of Higher Education, Science, and Technology of the Republic of Slovenia and the Slovenian Research Agency for financial support (P1-0230-0103). Dr. D. Žigon (Center for Mass Spectroscopy, “Jožef Stefan” Institute, Ljubljana, Slovenia) is gratefully acknowledged for the mass measurements. This work was partly supported with the infrastructure of the EN-FIST Centre of Excellence, Trg Osvobodilne fronte 13, SI-1000 Ljubljana, Slovenia. We also thank L. Žnideršič for laboratory assistance.

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Authors and Affiliations

  1. Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000, Ljubljana, Slovenia

    Bogdan Štefane & Franc Požgan

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  1. Bogdan Štefane
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  2. Franc Požgan
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Correspondence to Franc Požgan.

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Štefane, B., Požgan, F. Oxydehydrogenative aromatization of fused 3-aminopyran-2-ones on carbon surfaces: a simple approach towards 3-amino-5-hydroxycoumarin derivatives. Monatsh Chem 145, 1329–1335 (2014). https://doi.org/10.1007/s00706-014-1227-4

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  • DOI: https://doi.org/10.1007/s00706-014-1227-4

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