Quinones are an important class of naturally occurring compounds, which demonstrate antimicrobial and anticancer activities. In view of their biological activity, especially the quinones bearing N-heterocyclic rings have elicited considerable interest. Tetrahydroisoquinoline-5,8-diones and isoquinoline-5,8-diones have been used as a structural template for the synthesis of naturally occurring potent antibiotics such as saframycins, lemonomycin and bostrycoidin. Also the isoindole analogues, such as bhimamycin C and bhimamycin D, display a wide range of biological effects.
Although the (tetrahydro)benzo[g]isoquinoline-5,10-diones and benzo[f]isoindole-4,9-diones have attracted considerable attention in literature, to date only a limited number of synthetic pathways was developed, and none of these addresses the construction of 2-substituted 1,2,3,4-tetrahydro-benz[g]isoquinoline-5,10-diones.
We developed a general synthetic strategy for these classes of compounds, which consists of the synthesis of a 1,4-naphthoquinone (or a 1,4-dimethoxynaphthalene in case of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones), containing a N-protected aminoalkyl group at C-3 and a leaving group at the C-2-methylene group. An intramolecular substitution, an optional N-alkylation and a subsequent oxidation afford the desired target compounds.
Original languageEnglish
Title of host publication17th International Conference on Organic Synthesis (ICOS-17), June 22-27, 2008 Daejeon (Korea)
Pages20
Number of pages1
Publication statusPublished - 22 Jun 2008
EventFinds and Results from the Swedish Cyprus Expedition: A Gender Perspective at the Medelhavsmuseet - Stockholm, Sweden
Duration: 21 Sep 200925 Sep 2009

Conference

ConferenceFinds and Results from the Swedish Cyprus Expedition: A Gender Perspective at the Medelhavsmuseet
CountrySweden
CityStockholm
Period21/09/0925/09/09

    Research areas

  • 2-azaanthraquinones, napthalene, ring closure, napthoquinone

ID: 1715300