The synthesis of benzothiadiazines, benzothiadiazepines and benzothiadiazocines from intramolecular azide reactions and iodocyclisations

Patel, Nilesh, Chambers, Christopher Steven and Hemming, Karl (2009) The synthesis of benzothiadiazines, benzothiadiazepines and benzothiadiazocines from intramolecular azide reactions and iodocyclisations. Synlett, 2009 (18). pp. 3043-3047. ISSN 09365214

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Abstract

N-Homoallyl-substituted (2-aminoaryl)sulfonamides undergo intramolecular iodocyclisation to furnish aziridine-fused 1,2,6-benzothiadiazocines. The identical aziridine-fused 1,2,6-benzothiadiazocines were also available from an intramolecular azide to alkene 1,3-diploar cycloaddition involving the corresponding N-homoallylic (2-azidoaryl)sulfonamides in boiling carbon tetrachloride. The use of boiling DMF as solvent for the same reaction gave pyrrolo-fused benzothiadiazines. Intramolecular azide-alkene cycloadditions also allowed access to aziridine-fused pyrrolobenzothiadiazepines and pyrrolobenzodiazepines

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