Stereoselective Synthesis of Benzo[e][1,4]oxazino[4,3-a][1,4]diazepine-6,12-diones with Two Diversity Positions
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
- Klíčová slova
- benzodiazepine, morpholine, oxazine, solid-phase synthesis, stereoselective synthesis, triethylsilane,
- MeSH
- benzodiazepiny chemická syntéza chemie MeSH
- cyklizace MeSH
- katalýza MeSH
- molekulární struktura MeSH
- oxaziny chemická syntéza chemie MeSH
- stereoizomerie MeSH
- techniky kombinatorické chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- benzodiazepiny MeSH
- oxaziny 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
Citace poskytuje Crossref.org
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