Synthesis of benzo[f]isoindole-4,9-diones.
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.
Claessens
Sven
S
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Jacobs
Jan
J
Van Aeken
Sam
S
Tehrani
Kourosch Abbaspour
KA
De Kimpe
Norbert
N
D001688:Biological Products / Q000737:chemistry; D054833:Isoindoles / Q000138:chemical synthesis*; D009281:Naphthalenes / Q000737:chemistry; D010084:Oxidation-Reduction; D011809:Quinones / Q000737:chemistry
D001688:Biological Products; D054833:Isoindoles; D009281:Naphthalenes; D011809:Quinones