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

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Girard, Y; Hamel, P; Thérien, M; Springer, JP; Hirshfield, J

Published Date

  • September 1, 1987

Published In

Volume / Issue

  • 52 / 18

Start / End Page

  • 4000 - 4006

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00227a012

Citation Source

  • Scopus