title: Synthesis of tetrahydro-1,4-benzodiazepine-2-ones on hydrophilic polyamide SynPhase lanterns.
abstract: Solid-phase synthesis is greatly dependent on the solid support. Here, we report the use of a new hydrophilic grafted surface on SynPhase lanterns in solid-phase organic chemistry. A convenient and facile solid-phase synthesis of disubstituted 1,4-benzodiazepine-2-ones on polyamide SynPhase lanterns is described. The key step of the synthesis involved a reduction-cyclization of a nitroaryl methyl ester with a mixture of tin(II) chloride dihydrate and ammonium acetate in water and ethanol at elevated temperature to give the desired target compounds. A library of 21 disubstituted 1,4-benzodiazepine-2-ones was prepared.
authors.affiliation: Mimotopes Pty Ltd, 11 Duerdin Street, Clayton, Victoria 3168 Australia.
authors.forename: Zemin
authors.initials: Z
authors.lastname: Wu
authors.forename: Francesca
authors.initials: F
authors.lastname: Ercole
authors.forename: Michael
authors.initials: M
authors.lastname: FitzGerald
authors.forename: Senake
authors.initials: S
authors.lastname: Perera
authors.forename: Phil
authors.initials: P
authors.lastname: Riley
authors.forename: Rhonda
authors.initials: R
authors.lastname: Campbell
authors.forename: Yen
authors.initials: Y
authors.lastname: Pham
authors.forename: Philip
authors.initials: P
authors.lastname: Rea
authors.forename: Saman
authors.initials: S
authors.lastname: Sandanayake
authors.forename: Marc N
authors.initials: MN
authors.lastname: Mathieu
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Bray
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Ede
mesh_terms: D001570:Benzodiazepinones / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009757:Nylons / Q000138:chemical synthesis* / Q000737:chemistry; D011137:Polystyrenes / Q000737:chemistry
chemical_list: D001570:Benzodiazepinones; D007202:Indicators and Reagents; D009757:Nylons; D011137:Polystyrenes