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Reaction of ortho-ortho-dimethylphenacyl-halides with formamide. Formation of 4(5)-(ortho-ortho-dimethylbenzoyl)imidazoles

, : Reaction of ortho-ortho-dimethylphenacyl-halides with formamide. Formation of 4(5)-(ortho-ortho-dimethylbenzoyl)imidazoles. Il Farmaco; Edizione Scientifica 33(5): 364-381

Reaction of 2,3,5,6-tetramethylphenacyl halides with formamide did not produce the expected 4(5)-(2,3,5,6-tetramethylphenyl)imidazole, but 4(5)-(2,3,5,6-tetramethylbenzoyl)imidazole (VII) was isolated as the major product together with 5-(2,3,5,6-tetramethylphenyl)oxazole (III), alpha-formylamino-2,3,5,6-tetramethylacetophenone (IV) and alpha-chloro-beta-amino-vinyl 2,3,5,6-tetramethylphenyl ketone (IX) as by-products. The corresponding mesitylene derivatives gave analogous results, whereas 4(5)-(2-methylphenyl)imidazole was obtained from 2-methylphenacyl bromide as expected according to the Bredereck's reaction. The structure of the isolated compounds were elucidated by element analysis, mass, I.R., U.V. and N.M.R. spectra, and by chemical reactivity.


PMID: 738454

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