Ring contraction of 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides: access to 4H-benzo[b][1,4]thiazine 1,1-dioxides
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25564930
DOI
10.1021/jo502713k
Knihovny.cz E-resources
- MeSH
- Benzodiazepinones chemistry MeSH
- Epoxy Compounds chemistry MeSH
- Nitrobenzenes chemistry MeSH
- Thiadiazines chemistry MeSH
- Thiazines chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 2-nitrobenzenesulfenyl chloride MeSH Browser
- Benzodiazepinones MeSH
- Epoxy Compounds MeSH
- Nitrobenzenes MeSH
- Thiadiazines MeSH
- Thiazines MeSH
We report an efficient synthesis of 4H-benzo[b][1,4]thiazine 1,1-dioxides via unprecedented ring contraction of 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides under mild conditions involving carbon-sulfur bond formation. 2,5-Dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides are easily accessible from commercially available building blocks, including Fmoc-protected amino acids, 2-nitrobenzenesulfonyl chlorides, and bromo ketones. Benzothiazine 1,1-dioxides represent pharmacologically relevant derivatives with biological, medicinal, and industrial applications.
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