Mannich-Type Addition Reactions between Lithium Derivatives of Benzo[ d] thiazoles and N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimine: Convenient Generalized Synthesis of Bis( benzothiazole)s

This study describes the anomalous outcome of the Mannich-type reaction of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine and Li derivatives of benzo[d]thiazoles, which offers a convenient and generalized method for the synthesis of biologically relevant (E)-1,2-bis(2-benzothiazolyl)ethanes. The mechanism, scope, and scalability of this new reaction are discussed.