Stereoselective Synthesis of Benzo[e][1,4]oxazino[4,3-a][1,4]diazepine-6,12-diones with Two Diversity Positions
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- benzodiazepine, morpholine, oxazine, solid-phase synthesis, stereoselective synthesis, triethylsilane,
- MeSH
- Benzodiazepines chemical synthesis chemistry MeSH
- Cyclization MeSH
- Catalysis MeSH
- Molecular Structure MeSH
- Oxazines chemical synthesis chemistry MeSH
- Stereoisomerism MeSH
- Combinatorial Chemistry Techniques MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Benzodiazepines MeSH
- Oxazines MeSH
Herein, we report a stereoselective formation of tetrahydro-6H-benzo[e][1,4]oxazino[4,3-a][1,4]diazepine-6,12(11H)-diones. Their preparation consisted in solid-phase synthesis of linear intermediates starting from polymer-supported Ser(tBu)-OH. Using various 2-nitrobenzoic acids and bromoketones, the key intermediates were obtained in five steps and subjected to trifluoroacetic acid-mediated cleavage from the resin, followed by stereoselective reduction with triethylsilane. Subsequent catalytic hydrogenation of the nitro group and cyclization yielded the target compounds with full retention of the C12a stereocenter configuration.
Department of Organic Chemistry Faculty of Science Palacký University 771 46 Olomouc Czech Republic
JEOL Resonance Inc Musashino 3 1 2 Akishima Tokyo 196 8558 Japan
References provided by Crossref.org
Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine
