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.
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