7730-40-7Relevant academic research and scientific papers
Synthesis of 1-alkyl-2-(trifluoromethyl)azetidines and their regiospecific ring opening toward diverse α-(trifluoromethyl)amines via intermediate azetidinium salts
Kenis, Sara,D'Hooghe, Matthias,Verniest, Guido,Dang Thi, Tuyet Anh,Pham The, Chinh,Van Nguyen, Tuyen,De Kimpe, Norbert
, p. 5982 - 5992 (2012/09/21)
A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl) azetidines as a new class of constrained azaheterocycles was developed starting from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.
