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Synfacts 2006(2): 0174-0174  
DOI: 10.1055/s-2005-921763
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Amino-1,2,4-benzothiadiazine 1,1-Dioxides

Contributor(s): Yasuhiro Uozumi, Atsushi Ohtaka
C. Blackburn*, A. Achab, A. Elder, S. Ghosh, J. Guo, G. Harriman, M. Jones
Millennium Pharmaceuticals, Cambridge, USA
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Publikationsdatum:
23. Januar 2006 (online)

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Significance

The authors have reported the preparation of 3-amino-1,2,4-benzothiadiazine 1,1-dioxides from polymer-supported iminophosphoranes and isocyanates. Thus, the reactions of o-azidobenzenesulfonamides 1 with polymer-supported triphenylphosphine were performed in dichloromethane under mild conditions to give polymer-supported iminophosphoranes 2. Treatment of 2 with isocyanates afforded 3-amino-1,2,4-benzothiadiazine 1,1-dioxides 3 in moderate to good yields.