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

Fingerprint

sulfoxide
Azides
Oxides
Sulfoxides
Isoxazoles
Nitriles
triphenylphosphine

Cite this

Hemming, Karl ; Loukou, Christina ; Elkatip, Sinem ; Smalley, Robert K. / The First aza-Wittig Reaction Involving a non-Cumulated Sulfoxy Group. In: Synlett. 2004 ; No. 1. pp. 101-105.
@article{a2c8d8b0961642448893632932bebfed,
title = "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. 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.",
keywords = "1,3-dipolar cycloadditions, 2,1-benzothiazine, Aza-Wittig reaction, Sulfimide, Sulfoxides",
author = "Karl Hemming and Christina Loukou and Sinem Elkatip and Smalley, {Robert K.}",
year = "2004",
month = "1",
day = "5",
doi = "10.1055/s-2003-43352",
language = "English",
pages = "101--105",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "1",

}

The First aza-Wittig Reaction Involving a non-Cumulated Sulfoxy Group. / Hemming, Karl; Loukou, Christina; Elkatip, Sinem; Smalley, Robert K.

In: Synlett, No. 1, 05.01.2004, p. 101-105.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The First aza-Wittig Reaction Involving a non-Cumulated Sulfoxy Group

AU - Hemming, Karl

AU - Loukou, Christina

AU - Elkatip, Sinem

AU - Smalley, Robert K.

PY - 2004/1/5

Y1 - 2004/1/5

N2 - 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.

AB - 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.

KW - 1,3-dipolar cycloadditions

KW - 2,1-benzothiazine

KW - Aza-Wittig reaction

KW - Sulfimide

KW - Sulfoxides

UR - http://www.scopus.com/inward/record.url?scp=0346970813&partnerID=8YFLogxK

U2 - 10.1055/s-2003-43352

DO - 10.1055/s-2003-43352

M3 - Article

SP - 101

EP - 105

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 1

ER -