Synthesis of Benzothiazinones from Benzoyl Thiocarbamates: Application to Clinical Candidates for Tuberculosis Treatment

    • William Connorsa
    • Ryan DeKortea
    • Simon C. C. Lucasb
    • Ariamala Gopalsamyb
    • Robert E Zieglera
    • aAstraZeneca Pharmaceuticals LP, Medicinal Chemistry, United States
    • bAstraZeneca Pharmaceuticals LP, Hit Discovery, United Kingdom

    Benzothiazinones are a structural motif found in biologically active compounds, such as the clinical candidates BTZ-043 and Macozinone for the treatment of tuberculosis. We describe a robust, two-step method to synthesize 2-amino-substituted benzothiazinones from benzoyl thiocarbamates, which were prepared in a one-pot procedure from benzoyl chlorides. The intramolecular cyclization and ethoxy displacement steps were also amenable to adoption in continuous flow as exemplified by select substrates.

    Read the publication that featured this abstract

    Get in touch

    For more information on flow chemistry systems and services please use the contact methods below.

    Call us on +44 (0)1284 728659 or Email us