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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

Publication ,  Journal Article
Girard, Y; Hamel, P; Thérien, M; Springer, JP; Hirshfield, J
Published in: Journal of Organic Chemistry
September 1, 1987

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.

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Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

September 1, 1987

Volume

52

Issue

18

Start / End Page

4000 / 4006

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

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Girard, Y., Hamel, P., Thérien, M., Springer, J. P., & Hirshfield, J. (1987). 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 of Organic Chemistry, 52(18), 4000–4006. https://doi.org/10.1021/jo00227a012
Girard, Y., P. Hamel, M. Thérien, J. P. Springer, and J. Hirshfield. “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 of Organic Chemistry 52, no. 18 (September 1, 1987): 4000–4006. https://doi.org/10.1021/jo00227a012.
Girard Y, Hamel P, Thérien M, Springer JP, Hirshfield J. 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 of Organic Chemistry. 1987 Sep 1;52(18):4000–6.
Girard, Y., et al. “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 of Organic Chemistry, vol. 52, no. 18, Sept. 1987, pp. 4000–06. Scopus, doi:10.1021/jo00227a012.
Girard Y, Hamel P, Thérien M, Springer JP, Hirshfield J. 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 of Organic Chemistry. 1987 Sep 1;52(18):4000–4006.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

September 1, 1987

Volume

52

Issue

18

Start / End Page

4000 / 4006

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry