First Synthesis of Sulfoxides and Sulfones in the 3H-Phenothiazin-3-one and 5H-Benzo[a ]phenothiazin-5-one Ring Systems. Addition Reactions with Nucleophiles
We report the first synthesis of sulfoxides and sulfones in the 3H-phenothiazin-3-one and 5H-benzo[a]-phenothiazin-5-one ring systems. The pronounced reactivity of the parent compounds 2a, 2b, 4a, and 4b does not allow their isolation, but they can be conveniently trapped, as various types of adducts, with nucleophiles such as water, alcohols, and amines. The monoadduct 16b of 3-oxo-3H-phenothiazine 5,5-dioxide with n-propylamine rearranges into a derivative of the novel oxazolo[5,4-c]phenothiazine ring system (17). © 1987, American Chemical Society. All rights reserved.
Girard, Y; Hamel, P; Thérien, M; Springer, JP; Hirshfield, J
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