Umpolung Strategy for α,α’‐Functionalization of Ketones with 2‐Aminothiophenols: Stereoselective Access to Spirobis(1,4‐benzothiazines)

T .B. Nguyen (1) , Pascal Retailleau

1 ICSN - Institut de Chimie des Substances Naturelles

Strong Brønsted acids were found to catalyze the oxidative condensation of 2-aminothiophenols with aryl alkyl ketones in DMSO to provide a wide range of complex 2-arylbenzothiazines. With acetophenones, dimeric 2arylbenzothiazines were formed. On the other hand, the reaction with propiophenones resulted in 2:1 adducts whereas 1:1 adducts were produced with isobutyrophenones, benzoylacetonitrile and ethyl benzoylacetate.

Mots clés: sulfur; 1; 4-benzothiazines; DMSO; redox condensation

Domaines: Chimie

T .B. Nguyen, Pascal Retailleau. Umpolung Strategy for α,α’‐Functionalization of Ketones with 2‐Aminothiophenols: Stereoselective Access to Spirobis(1,4‐benzothiazines). Advanced Synthesis and Catalysis, 2020, 362 (18), pp.3824-3829. ⟨10.1002/adsc.202000725⟩. ⟨hal-02993881⟩