Journal of Organic Chemistry p. 8449 - 8454 (1997)
Update date:2022-08-05
Topics:
Shilcrat, Susan C.
Mokhallalati, Mohamed K.
Fortunak, Joseph M. D.
Pridgen, Lendon N.
A new method is presented for the preparation of 1,2-disubstitued-1H-imidazole-5-carboxaldehydes by the reaction of N-monosubstituted amidines with 2-halo-3-alkoxy-2-propenals. The reaction is highly regioselective with ratios of 1,2,5:1,2,4-imidazolecarboxaldehydes ranging from 85:15 to 100: 0. This methodology could be extended with similar results to the synthesis of imidazole-5-nitriles by the reaction of 2-bromo-3-methoxy-2-propenenitrile with N-monosubstituted amidines.
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Doi:10.1039/c4nj02371d
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(1997)
