1,2,6-Thiadiazine 1-Oxides: Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides.
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. peerReviewed
Synthesis of trifluoromethyl-substituted 1,2,6-thiadiazine 1-oxides from sulfonimidamides under mechanochemical conditions
TBS-protected or NH-sulfonimidamides react with β-alkoxyvinyl trifluoromethylketones under solvent-free mechanochemical conditions to give 3-trifluoromethyl-substituted three-dimensional 1,2,6-thiadiazine 1-oxides. C4-Functionalized products can be obtained by starting from cyclic enones and brominations of the initially formed heterocycles. The stability of the products was investigated by varying the pH value and storage under aerobic conditions.
CCDC 2109381: Experimental Crystal Structure Determination
Related Article: Marco Thomas Passia, Jan-Hendrik Sch��bel, Niklas Julian Lentelink, Khai-Nghi Truong, Kari Rissanen, Carsten Bolm|2021|Org.Biomol.Chem.|19|9470|doi:10.1039/D1OB01912K
CCDC 1985011: Experimental Crystal Structure Determination
Related Article: Jan-Hendrik Schöbel, Marco Thomas Passia, Nadja Anna Wolter, Rakesh Puttreddy, Kari Rissanen, Carsten Bolm|2020|Org.Lett.|22|2702|doi:10.1021/acs.orglett.0c00666
CCDC 2109331: Experimental Crystal Structure Determination
Related Article: Marco Thomas Passia, Jan-Hendrik Sch��bel, Niklas Julian Lentelink, Khai-Nghi Truong, Kari Rissanen, Carsten Bolm|2021|Org.Biomol.Chem.|19|9470|doi:10.1039/D1OB01912K