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

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. Th...

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Bibliographic Details
Published in:Synlett 2004-01, Vol.2004 (1), p.101-105
Main Authors: Hemming, Karl, Loukou, Christina, Elkatip, Sinem, Smalley, Robert K.
Format: Article
Language:English
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-43352