The First aza-Wittig Reaction Involving a non-Cumulated Sulfoxy Group

Karl Hemming, Christina Loukou, Sinem Elkatip, Robert K. Smalley

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

3-(Aryliminophosphoranyl)-5-phenyl-4-arylsulfoxy-isoxazoles undergo ring closure via an intramolecular aza-Wittig type reaction of an iminophosphorane onto a non-cumulated sulfoxide. The products obtained are isoxazolo[4,3-c]-2,1- benzothiazines, a hitherto unreported heterocyclic system. This is the first example of the construction of the sulfimide linkage (S=N) via a Wittig type process involving non-cumulated sulfoxides. The requisite iminophosphoranes were synthesised using the Staudinger reaction of an azide with triphenylphosphine. Other key steps include the regioselective addition of a carbanion to a nitrile oxide in the presence of an azide, and the synthesis and use of the little reported o-azidobenzonitrile oxide.

Original languageEnglish
Pages (from-to)101-105
Number of pages5
JournalSynlett
Issue number1
DOIs
Publication statusPublished - 5 Jan 2004

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