Synthesis of benzothiadiazines, benzothiadiazepines, and benzothiadiazocines from intramolecular azide reactions and iodocyclisations

Nilesh Patel, Christopher S. Chambers, Karl Hemming

Research output: Contribution to journalArticle

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3043-3047
Number of pages5
JournalSynlett
Issue number18
Early online date9 Oct 2009
DOIs
Publication statusPublished - 21 Dec 2009

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