Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 3, Pages 1795-1801Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502713k
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Funding
- Department of Chemistry and Biochemistry, University of Notre Dame
- Czech Science Foundation (GACR) [P207/12/0473]
- European Social Fund [CZ.1.07/2.4.00/31.0130, CZ.1.07/2.3.00/30.0060]
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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 carbonsulfur 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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