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One-pot synthesis of 2-aminobenzoxazole derivatives using acetic acid as an electrolyte under electrochemical conditions

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Abstract

In this work, we have developed an electrochemical method to prepare 2-aminobenzoxazole by using acetic acid as an electrolyte. The key benefits of this method are being cleaner reaction pattern with minimum impurity formation, no metal catalyst used, high atom economy, robust, scalable and having a broad substrate scope. Previously, electrochemical conversions were reported with the addition of a supporting electrolyte such as tetrabutyl ammoniumbromide, sodium iodide and lithium perchlorate, but in this conversion we have removed the use of all supporting electrolytes and we have used acetic acid, which plays a dual role of opening the benzoxazole moiety and works as an electrolyte. All these electrochemical conversions were done on a electrochemical reactor prepared through a 5v mobile charger having a output current density of 0.35A.cm−2. Various pharmaceutically relevant secondary amines are coupled with benzoxazole in high yield by using this set-up. All the conversions were done at room temperature and total conversion observed in 6 h. The scale of the conversion ranges from milligram to gram. Active intermediate of Suvorexant, a medicine for insomnia, was prepared by using this method.

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All the experimental procedure, 1H NMR, CMR and LCMS data are available with the supporting information.

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Acknowledgements

We would like to thank Shri M M Patel Institute of Science and Research, Department of Chemistry, Kadi Sarva Vishwavidlaya, for providing their intellectual, technical and logistical support throughout the research work.

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Authors and Affiliations

  1. Department of Chemistry, Shri MM Patel Institute of Sciences and Research, Kadi Sarva Vishwavidyalaya, Gandhinagar, Gujarat, 382024, India

    Tanay Ghoshal & Tarun M. Patel

Authors
  1. Tanay Ghoshal
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  2. Tarun M. Patel
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Contributions

TG is the main author and he collected, analysed, conceived and wrote the first draft. TP reviewed the draft and gave additional inputs to improve the scientific rigour required. Both authors read and approved the final draft for publication.

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Correspondence to Tarun M. Patel.

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Ghoshal, T., Patel, T.M. One-pot synthesis of 2-aminobenzoxazole derivatives using acetic acid as an electrolyte under electrochemical conditions. J IRAN CHEM SOC 18, 2241–2248 (2021). https://doi.org/10.1007/s13738-021-02184-1

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