Fabio Lima - A Multistep Flow Process for the Synthesis of Highly Functionalized Benzoxazoles

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  Publication Details (including relevant citation   information):

  DOI : 10.1021/ol402706a

  Published on Web 10/22/2013


  Vol. 15, No. 21


  Jörg Sedelmeier, Fabio Lima, Alain Litzler, Benjamin Martin and   Francesco Venturoni


  An efficient and scalable transformation of 3-halo-N-acyl   anilines to the corresponding benzoxazoles within a continuous   flow reactor is reported. This transformation proceeds via   base-mediated deprotonation, ortho-lithiation, and intramolecular   cyclization to provide unstable lithiated benzoxazole moieties.   The subsequent in-line electrophilic quench results in the   formation of substituted benzoxazoles in high yield and quality.   Continuous flow technology allowed for accurate temperature   control and immediate in-line quench while minimizing the hold-up   time for the unstable lithiated intermediates thereby minimizing   associated byproduct formation.

  Address (URL): http://pubs.acs.org/doi/abs/10.1021%2Fol402706a