Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine 2,2-dioxides and 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

doi:10.1039/C9OB01657K

Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine 2,2-dioxides and 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

GlaxoSmithKline

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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 language	English
Pages (from-to)	9585-9604
Number of pages	20
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	44
Early online date	31 Oct 2019
DOIs	https://doi.org/10.1039/C9OB01657K
Publication status	Published - Nov 2019

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10.1039/C9OB01657KLicence: Unspecified

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Aiken, S., Anozie, K., De Azevedo, O., Cowan, L., Edgar, R., Gabbutt, C., Heron, B., Lawrence, P., Mills, A., Rice, C., Urquhart, M., & Zonidis, D. (2019). Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine 2,2-dioxides and 1,2-oxathiine 2,2-dioxides: Revisiting sulfene additions to enaminoketones. Organic and Biomolecular Chemistry, 17(44), 9585-9604. https://doi.org/10.1039/C9OB01657K

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title = "Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine 2,2-dioxides and 1,2-oxathiine 2,2-dioxides: Revisiting sulfene additions to enaminoketones",

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. ",

author = "Stuart Aiken and Kelechi Anozie and \{De Azevedo\}, Orlando and Lewis Cowan and Ross Edgar and Christopher Gabbutt and Bernard Heron and Pippa Lawrence and Abby Mills and Craig Rice and Mike Urquhart and Dimitrios Zonidis",

year = "2019",

month = nov,

doi = "10.1039/C9OB01657K",

language = "English",

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Aiken, S, Anozie, K, De Azevedo, O, Cowan, L, Edgar, R, Gabbutt, C , Heron, B, Lawrence, P, Mills, A, Rice, C, Urquhart, M & Zonidis, D 2019, 'Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine 2,2-dioxides and 1,2-oxathiine 2,2-dioxides: Revisiting sulfene additions to enaminoketones', Organic and Biomolecular Chemistry, vol. 17, no. 44, pp. 9585-9604. https://doi.org/10.1039/C9OB01657K

TY - JOUR

T1 - Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine 2,2-dioxides and 1,2-oxathiine 2,2-dioxides

T2 - Revisiting sulfene additions to enaminoketones

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

AU - Rice, Craig

AU - Urquhart, Mike

AU - Zonidis, Dimitrios

PY - 2019/11

Y1 - 2019/11

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/85074961739

U2 - 10.1039/C9OB01657K

DO - 10.1039/C9OB01657K

M3 - Article

SN - 1477-0520

VL - 17

SP - 9585

EP - 9604

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 44

ER -

Expedient synthesis of highly substituted 3,4-dihydro-1,2-oxathiine 2,2-dioxides and 1,2-oxathiine 2,2-dioxides: Revisiting sulfene additions to enaminoketones

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