title: N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China. zhgu@ustc.edu.cn.
authors.forename: Rui
authors.initials: R
authors.lastname: Zhu
authors.forename: Kai
authors.initials: K
authors.lastname: Yu
authors.forename: Zhenhua
authors.initials: Z
authors.lastname: Gu
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D003500:Cyclization; D004126:Dimethylformamide / Q000737:chemistry; D006358:Hot Temperature; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*
chemical_list: D000081:Acetamides; D000475:Alkenes; D062845:Chloroacetates; D010080:Oxazoles; C016272:N-bromoacetamide; D004126:Dimethylformamide; C009528:trichloroacetamide