1,2,6-Thiadiazine 1-Oxides: Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides
Jan‐Hendrik Schöbel, Marco T. Passia, Nadja Wolter, Rakesh Puttreddy, Kari Rissanen, Carsten Bolm
Abstract
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.
Topics & Concepts
ChemistryHalogenationRing (chemistry)CondensationDerivative (finance)PropargylSequence (biology)Medicinal chemistryStereochemistryOrganic chemistryCatalysisPhysicsEconomicsFinancial economicsBiochemistryThermodynamicsSynthesis and Catalytic ReactionsPhenothiazines and Benzothiazines Synthesis and ActivitiesSulfur-Based Synthesis Techniques