title: A new strategy for the synthesis of 1,4-benzodiazepine derivatives based on the tandem N-alkylation-ring opening-cyclization reactions of methyl 1-arylaziridine-2-carboxylates with N-[2-bromomethyl(phenyl)]trifluoroacetamides.
abstract: A new method for the synthesis of novel 1,4-benzodiazepine derivatives has been established from a one-pot reaction of methyl 1-arylaziridine-2-carboxylates with N-[2-bromomethyl(aryl)]trifluoroacetamides. The reaction proceeds through the N-benzylation and highly regioselective ring-opening reaction of aziridine by bromide anion followed by Et3N-mediated intramolecular nucleophilic displacement of the bromide by the amide nitrogen. The easy availability of starting materials, simple and convenient synthetic procedure, and formation of functionalized 1,4-benzodiazepine scaffold ready for further chemical manipulations render this strategy useful in synthetic and medicinal chemistry.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China.
authors.forename: Jin-Yuan
authors.initials: JY
authors.lastname: Wang
authors.forename: Xue-Fei
authors.initials: XF
authors.lastname: Guo
authors.forename: De-Xiang
authors.initials: DX
authors.lastname: Wang
authors.forename: Zhi-Tang
authors.initials: ZT
authors.lastname: Huang
authors.forename: Mei-Xiang
authors.initials: MX
authors.lastname: Wang
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000478:Alkylation; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D003500:Cyclization
chemical_list: D000081:Acetamides; D002264:Carboxylic Acids; D001569:Benzodiazepines; C468549:Bz-423