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Synthesis of 3-amino-1,2,4-benzothiadi- azine 1,1-dioxides via a tandem aza-Wittig/heterocumulene annulation
Authors:Blackburn Christopher  Achab Abe  Elder Amy  Ghosh Shomir  Guo Jianping  Harriman Geraldine  Jones Matthew
Institution:Department of Medicinal Chemistry, Millennium Pharmaceuticals, 35 Landsdowne Street, Cambridge, Massachusetts 02139, USA. chris.blackburn@mpi.com
Abstract:reaction: see text] Reaction of o-azidobenzenesulfonamides with polymer-supported triphenylphosphine affords the corresponding iminophosphoranes. Subsequent reaction with isocyanates gives 3-amino-1,2,4-benzothiadiazine 1,1-dioxides in high yields and purities. The reaction has been successfully applied to the synthesis of derivatives with various substituents at the 2- and 3-positions and in the benzenoid ring.
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