2,3-Dihydro-1,2,6-thiadiazine 1-Oxides by Biginelli-Type Reactions with Sulfonimidamides under Mechanochemical Conditions
Felix Krauskopf, Khai‐Nghi Truong, Kari Rissanen, Carsten Bolm
Abstract
H-free sulfonimidamides provide 2,3-dihydro-1,2,6-thiadiazine 1-oxides in high yields. The couplings are performed in a planetary ball mill under solvent-free mechanochemical conditions. Acetic acid or ytterbium triflate are used as catalysts. A representative product was characterized by X-ray single crystal structure analysis revealing molecular details of the highly functionalized three-dimensional heterocycle. Further product modifications lead to additional structural scaffolds.
Topics & Concepts
TrifluoromethanesulfonateChemistryAcetic acidCatalysisBall millBiginelli reactionMechanochemistryCrystal structureOrganic chemistrySolventChemical engineeringEngineeringQuinazolinone synthesis and applicationsPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Characterization of Heterocyclic Compounds