1,2,6-Thiadiazine 1-Oxides : Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides
Schöbel, Jan-Hendrik; Passia, Marco Thomas; Wolter, Nadja Anna; Puttreddy, Rakesh; Rissanen, Kari; Bolm, Carsten (2020). 1,2,6-Thiadiazine 1-Oxides : Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides. Organic Letters, 12 (7), 2702-2706. DOI: 10.1021/acs.orglett.0c00666
Published inOrganic Letters
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Unprecedented three-dimensional 1,2,6-thiadiazine 1-oxides have been prepared by an aza-Michael-addition/cyclization/condensation reaction sequence starting from sulfonimidamides and propargyl ketones. The products have been further functionalized by standard cross-coupling reactions, selective bromination of the heterocyclic ring, and conversion into a β-hydroxy substituted derivative. A representative product was characterized by single-crystal X-ray structure analysis.