Expedient Synthesis of highly Substituted 1,2-Oxathiine 2,2-dioxides

Revisiting sulfene additions to enaminoketones

Stuart Aiken, Kelechi Anozie, Orlando De Azevedo, Lewis Cowan, Ross Edgar, Christopher Gabbutt, Bernard Heron, Pippa Lawrence, Abby Mills, Craig Rice, Mike Urquhart, Dimitrios Zonidis

Research output: Contribution to journalArticle

Abstract

Diversely substituted 1,2-oxathiine 2,2-dioxides, including 3,5,6-triaryl-, 3,6-diaryl-, 3,5-diaryl-, 5,6-diaryl- and selected fused heterocyclic analogues, have been efficiently obtained by the application of a mild Cope elimination of a 4-amino moiety from the requisite 4-amino-3,4-dihydro-1,2-oxathiine 2,2-dioxides, which themselves were readily obtained by the addition of sulfenes to enaminoketones.
Original languageEnglish
JournalOrganic and Biomolecular Chemistry
Early online date31 Oct 2019
DOIs
Publication statusE-pub ahead of print - 31 Oct 2019

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Oxathiins
dioxides
synthesis
elimination
analogs
sulfaperine

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Aiken, Stuart ; Anozie, Kelechi ; De Azevedo, Orlando ; Cowan, Lewis ; Edgar, Ross ; Gabbutt, Christopher ; Heron, Bernard ; Lawrence, Pippa ; Mills, Abby ; Rice, Craig ; Urquhart, Mike ; Zonidis, Dimitrios. / Expedient Synthesis of highly Substituted 1,2-Oxathiine 2,2-dioxides : Revisiting sulfene additions to enaminoketones. In: Organic and Biomolecular Chemistry. 2019.
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abstract = "Diversely substituted 1,2-oxathiine 2,2-dioxides, including 3,5,6-triaryl-, 3,6-diaryl-, 3,5-diaryl-, 5,6-diaryl- and selected fused heterocyclic analogues, have been efficiently obtained by the application of a mild Cope elimination of a 4-amino moiety from the requisite 4-amino-3,4-dihydro-1,2-oxathiine 2,2-dioxides, which themselves were readily obtained by the addition of sulfenes to enaminoketones.",
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Expedient Synthesis of highly Substituted 1,2-Oxathiine 2,2-dioxides : Revisiting sulfene additions to enaminoketones. / Aiken, Stuart; Anozie, Kelechi; De Azevedo, Orlando; Cowan, Lewis; Edgar, Ross; Gabbutt, Christopher; Heron, Bernard; Lawrence, Pippa; Mills, Abby; Rice, Craig; Urquhart, Mike; Zonidis, Dimitrios.

In: Organic and Biomolecular Chemistry, 31.10.2019.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Expedient Synthesis of highly Substituted 1,2-Oxathiine 2,2-dioxides

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AU - Aiken, Stuart

AU - Anozie, Kelechi

AU - De Azevedo, Orlando

AU - Cowan, Lewis

AU - Edgar, Ross

AU - Gabbutt, Christopher

AU - Heron, Bernard

AU - Lawrence, Pippa

AU - Mills, Abby

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AU - Urquhart, Mike

AU - Zonidis, Dimitrios

PY - 2019/10/31

Y1 - 2019/10/31

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AB - Diversely substituted 1,2-oxathiine 2,2-dioxides, including 3,5,6-triaryl-, 3,6-diaryl-, 3,5-diaryl-, 5,6-diaryl- and selected fused heterocyclic analogues, have been efficiently obtained by the application of a mild Cope elimination of a 4-amino moiety from the requisite 4-amino-3,4-dihydro-1,2-oxathiine 2,2-dioxides, which themselves were readily obtained by the addition of sulfenes to enaminoketones.

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