N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives.

A practical synthesis of 1-bromo-2-amino-3-butene derivatives from homoallylic trichloroacetimidates was reported. Simply heating the mixture of substrates and N-bromoacetamide in DMF at 90 °C would give the desired products in moderate to excellent yields. The reaction may proceed through a domino bromo-cyclization and elimination pathway. The synthesis of 4,5-dihydrooxazoles from 1-bromo-2-amino-3-butene derivatives was also investigated.