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Acid Catalyzed Direct-Amidation–Dehydrocyclization of 2-Hydroxy-acetophenones to Benzoxazoles by a One-Pot Sustainable Synthesis

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Abstract

A series of 2-methyl-benzoxazoles have been synthesized starting from 2-hydroxy-acetophenones via a one-pot three steps reaction. Hydroxylamonium salt has been used as amidation agent. The reaction occurs with different anions, but the best results is achieved with hydroxylamonium hydrchloride. Despite the number of consecutive stages, the reaction is highly selective. Mild reaction conditions and various solvents can be used, but trifluoroacetic acid is the preferred. Almost, complete recovery of the trifluoroacetic acid can be achieved by vacuum distillation. The role of trifluoroacetic acid, as well as, of the hydroxylamonium salt suggests a cooperative effect leading to high selective formation of 2-methyl-benzoxazoles.

Graphical Abstract

One-pot TFA catalyzed synthesis of benzoxazoles starting from 2-hydroxyacetophenones.

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Acknowledgments

Financial support by Ca’ Foscari University of Venice is gratefully acknowledged (ADIR fund 2012). A special thank to Mr. Claudio Tortato for the helpful discussions.

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Authors and Affiliations

  1. Department of Molecular Science and Nanosystems, Ca’ Foscari University, 2137 Dorsoduro, 30123, Venice, Italy

    Elia Rancan, Giuseppe Quartarone, Lucio Ronchin & Andrea Vavasori

  2. Department of Environmental Science, Informatics and Statistics, Ca’ Foscari University, 2137 Dorsoduro, 30123, Venice, Italy

    Fabio Aricò

  3. Green Chemistry Group, 2137 Dorsoduro, 30123, Venice, Italy

    Elia Rancan, Fabio Aricò, Giuseppe Quartarone, Lucio Ronchin & Andrea Vavasori

Authors
  1. Elia Rancan
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  2. Fabio Aricò
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  3. Giuseppe Quartarone
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  4. Lucio Ronchin
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  5. Andrea Vavasori
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Corresponding author

Correspondence to Lucio Ronchin.

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Rancan, E., Aricò, F., Quartarone, G. et al. Acid Catalyzed Direct-Amidation–Dehydrocyclization of 2-Hydroxy-acetophenones to Benzoxazoles by a One-Pot Sustainable Synthesis. Catal Lett 145, 939–946 (2015). https://doi.org/10.1007/s10562-014-1466-3

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  • DOI: https://doi.org/10.1007/s10562-014-1466-3

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