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Davis–Beirut reaction inspired nitroso Diels–Alder reaction
- Source :
- Tetrahedron Lett
- Publication Year :
- 2021
- Publisher :
- Elsevier BV, 2021.
-
Abstract
- A Davis–Beirut reaction inspired nitroso Diels–Alder protocol is reported. The starting material for the procedure is a nitrophenyl moiety with the para position appropriately substituted with a 2°-amine (see 5) or 2°-alcohol (see 6). Deprotonation at the benzylic position followed by concomitant oxidation of the benzylic position and reduction of the nitro moiety delivers a nitrosophenyl intermediate, which subsequently undergoes a nitroso Diels–Alder reaction. This one-pot procedure delivers aryldihydro-1,2-oxazines in moderate yields.
- Subjects :
- inorganic chemicals
010405 organic chemistry
Chemistry
organic chemicals
fungi
Organic Chemistry
Nitroso
010402 general chemistry
01 natural sciences
Biochemistry
Medicinal chemistry
Article
0104 chemical sciences
Para position
chemistry.chemical_compound
Deprotonation
Drug Discovery
Nitro
Moiety
Davis–Beirut reaction
Diels–Alder reaction
Subjects
Details
- ISSN :
- 00404039
- Volume :
- 69
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi.dedup.....8b7a04be93ad1ac6b5b03947ac3c0578