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CC BY ND NC 4.0 · SynOpen 2018; 02(02): 0105-0113
DOI: 10.1055/s-0036-1591977
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One-pot Synthesis of 2-Substituted 4H-Chromeno[3,4-d]oxazol-4-ones from 4-Hydroxy-3-nitrocoumarin and Acids in the Presence of Triphenylphosphine and Phosphorus Pentoxide under Microwave Irradiation

Authors

  • T. D. Balalas

    a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece   Email: klitinas@chem.auth.gr

  • G. Stratidis

    a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece   Email: klitinas@chem.auth.gr

  • D. Papatheodorou

    a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece   Email: klitinas@chem.auth.gr

  • E.-E. Vlachou

    a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece   Email: klitinas@chem.auth.gr

  • C. Gabriel

    b   Center for Research of the Structure of Matter, Magnetic Resonance Laboratory, Department of Chemical Engineering, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece

  • D. J. Hadjipavlou-Litina

    c   Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece

  • K. E. Litinas*

    a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece   Email: klitinas@chem.auth.gr
Further Information

Publication History

Received: 31 January 2018

Accepted after revision: 13 March 2018

Publication Date:
17 April 2018 (online)

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Graphical Abstract

Abstract

2-Substituted 4H-chromeno[3,4-d]oxazol-4-ones are prepared from 4-hydroxy-3-nitrocoumarin and acids by one-pot reaction in the presence of PPh3 and P2O5 under microwave irradiation or by one-pot two-step reactions in the presence of Pd/C and hydrogen and then P2O5 under microwave irradiation. The fused oxazolocoumarins were also synthesized from 3-amido-4-hydroxycoumarins and P2O5 under microwave irradiation. The 3-amido-4-hydroxycoumarins are obtained almost quantitatively from 4-hydroxy-3-nitrocoumarin, acids and PPh3 under microwave irradiation, or in the presence of Pd/C and H2 on heating. Preliminary biological tests indicate significant inhibition of soybean lipoxygenase and antilipid peroxidation for both oxazolocoumarins and o-hydroxyamidocoumarins.

Key words

oxazolocoumarins - PPh3 - reduction - phosphorus pentoxide - microwaves - Pd/C

Supporting Information