Tetrahedron p. 6249 - 6262 (1989)
Update date:2022-08-03
Topics: Nucleophile Oxazoles Chemical Reaction Experimental conditions
Hassner, Alfred
Fischer,Bilha
An investigation of the reaction of variously substituted oxazoles 1a-1 with Br2 in methanol revealed the formation of non-aromatic addition products.In general the presence of an aromatic substituent at the 4-position of oxazoles or the presence of a 4-methyl group if the 2-substituent is also aliphatic favors formation of 2,5-dimethoxy-3-oxazolines 3, while an aromatic substituent at the 2-position favors formation of ring-opened amides 2 or 7 or of 4,5-dimethoxy-2-oxazolines 5.Valuable information about intermediates in these reaction can be obtained by following the bromination of 1 in CD3OD by 1H- and 13C-NMR.
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