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

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-oxa...

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Published in:Organic & biomolecular chemistry 2019-11, Vol.17 (44), p.9585-964
Main Authors: Aiken, Stuart, Anozie, Kelechi, de Azevedo, Orlando D. C. C, Cowen, Lewis, Edgar, Ross J. L, Gabbutt, Christopher D, Heron, B. Mark, Lawrence, Philippa A, Mills, Abby J, Rice, Craig R, Urquhart, Mike W. J, Zonidis, Dimitrios
Format: Article
Language:English
Subjects:
Crystallography
Dioxides
Substitutes
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Summary: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. The addition of sulfenes to substituted enaminoketones, followed by a facile Cope elimination, provides efficient access to a diverse series of 1,2-oxathiine 2,2-dioxides.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01657k