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 KingdomRead the publication that featured this abstract
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.
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