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Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-X Mode: Convenient Route to 3-Oxazolines.
- Source :
-
The Journal of organic chemistry [J Org Chem] 1996 May 31; Vol. 61 (11), pp. 3749-3752. - Publication Year :
- 1996
-
Abstract
- The mild base-promoted reaction of methyl 2-phenyl-1-azirine-3-acetate (1) with aldehydes and acetone provides a new and simple route to the 3-oxazolines 5, which are formed in good yields by the electrophilic trapping of an imino anion produced by C-N bond cleavage in the 1-azirine enolate intermediate 6. Chloranil oxidation of 5 containing an aromatic substituent at C-2 affords oxazoles 7, while reaction of 5 containing an aliphatic group at C-2 produces 5-methylene-3-oxazolines 8 and 5-spiro-2-oxazolines 9 in addition to 7.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 61
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 11667224
- Full Text :
- https://doi.org/10.1021/jo9518866