title: One-Pot Procedure for the Synthesis of 1,5-Benzodiazepines from N-Allyl-2-bromoanilines.
abstract: A new one-pot procedure that includes an initial titanium-catalyzed intermolecular hydroaminoalkylation of N-allyl-2-bromoanilines with N-methylanilines and a subsequent intramolecular Buchwald-Hartwig amination directly gives access to pharmacologically relevant 1,5-benzodiazepines. The process takes advantage of the excellent regioselectivity of the initial hydroaminoalkylation performed in the presence of a titanium mono(formamidinate) catalyst and the fact that the exclusively formed branched hydroaminoalkylation products can only undergo palladium-catalyzed cyclization to 1,5-benzodiazepines.
authors.affiliation: Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26111, Oldenburg, Germany.
authors.forename: Marco
authors.initials: M
authors.lastname: Weers
authors.affiliation: Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26111, Oldenburg, Germany.
authors.forename: Lars H
authors.initials: LH
authors.lastname: Lühning
authors.affiliation: Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26111, Oldenburg, Germany.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Lührs
authors.affiliation: Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26111, Oldenburg, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Brahms
authors.affiliation: Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26111, Oldenburg, Germany.
authors.forename: Sven
authors.initials: S
authors.lastname: Doye
keywords: amination; amines; benzodiazepines; palladium; titanium