title: Synthesis of benzo[f]isoindole-4,9-diones.
abstract: A synthesis of benzo[f]isoindole-4,9-diones 1 is presented starting from the reaction of 2,3-bis(bromomethyl)-1,4-dimethoxynaphthalene 15 with primary amines affording 2,3-bis(aminomethyl)-1,4-dimethoxynaphthalenes 14, which could be converted by CAN-mediated oxidation in one step to benzo[f]isoindole-4,9-diones 1. An alternative synthesis of benzo[f]isoindole-4,9-diones 1 starts from 2,3-bis(bromomethyl)-1,4-naphthoquinone 9 via 2,3-dihydrobenzo[f]isoindoles 10 which spontaneously oxidize.
authors.affiliation: Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Sven
authors.initials: S
authors.lastname: Claessens
authors.forename: Jan
authors.initials: J
authors.lastname: Jacobs
authors.forename: Sam
authors.initials: S
authors.lastname: Van Aeken
authors.forename: Kourosch Abbaspour
authors.initials: KA
authors.lastname: Tehrani
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D001688:Biological Products / Q000737:chemistry; D054833:Isoindoles / Q000138:chemical synthesis*; D009281:Naphthalenes / Q000737:chemistry; D010084:Oxidation-Reduction; D011809:Quinones / Q000737:chemistry
chemical_list: D001688:Biological Products; D054833:Isoindoles; D009281:Naphthalenes; D011809:Quinones