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Scheme 3. Cascade Process for the Formation of C-
Substituted Benzoisothiazole 5
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In conclusion, we have shown that a range of thiadiazoles can
be combined effectively with benzyne precursors to deliver the
corresponding 3-substituted benzoisothiazoles. In particular,
the use of 3-(dialkyl)amino-4-hydroxythiadiazoles allows the
selective formation of 3-(dialkyl)amino-substituted benzoiso-
thiazoles, with the formal loss of a molecule of cyanic acid as a
byproduct. Good variation of the benzyne precursor was
possible, allowing the efficient preparation of a broad range of
3-aminobenzoisothiazoles.
(10) Carrington, D. E. L.; Clarke, K.; Scrowston, R. M. J. Chem. Soc.
C 1971, 3903.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
Experimental procedures and full characterization for all
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank the EPSRC for support of this study.
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