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

By Nilesh Patel, Christopher Steven Chambers and Karl Hemming

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 pyrrolobenzodiazepine

Topics: Q1, QD
Publisher: Georg Thieme Verlag
Year: 2009
OAI identifier: oai:eprints.hud.ac.uk:6198
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