Standard

A novel synthesis of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones, 2-aza-anthraquinones and benzo[f]isoindole-4,9-diones. / Deblander, Jurgen; Abbaspour Tehrani, Kourosch.

17th International Conference on Organic Synthesis (ICOS-17), June 22-27, 2008 Daejeon (Korea). 2008. p. 20.

Research output: Chapter in Book/Report/Conference proceedingMeeting abstract (Book)

Harvard

Deblander, J & Abbaspour Tehrani, K 2008, A novel synthesis of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones, 2-aza-anthraquinones and benzo[f]isoindole-4,9-diones. in 17th International Conference on Organic Synthesis (ICOS-17), June 22-27, 2008 Daejeon (Korea). pp. 20, Finds and Results from the Swedish Cyprus Expedition: A Gender Perspective at the Medelhavsmuseet, Stockholm, Sweden, 21/09/09.

APA

Deblander, J., & Abbaspour Tehrani, K. (2008). A novel synthesis of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones, 2-aza-anthraquinones and benzo[f]isoindole-4,9-diones. In 17th International Conference on Organic Synthesis (ICOS-17), June 22-27, 2008 Daejeon (Korea) (pp. 20)

Vancouver

Deblander J, Abbaspour Tehrani K. A novel synthesis of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones, 2-aza-anthraquinones and benzo[f]isoindole-4,9-diones. In 17th International Conference on Organic Synthesis (ICOS-17), June 22-27, 2008 Daejeon (Korea). 2008. p. 20

Author

BibTeX

@inbook{2a26eb57f7b1416698f842b1268fde58,
title = "A novel synthesis of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones, 2-aza-anthraquinones and benzo[f]isoindole-4,9-diones",
abstract = "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.",
keywords = "2-azaanthraquinones, napthalene, ring closure, napthoquinone",
author = "Jurgen Deblander and {Abbaspour Tehrani}, Kourosch",
year = "2008",
month = "6",
day = "22",
language = "English",
pages = "20",
booktitle = "17th International Conference on Organic Synthesis (ICOS-17), June 22-27, 2008 Daejeon (Korea)",

}

RIS

TY - CHAP

T1 - A novel synthesis of 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones, 2-aza-anthraquinones and benzo[f]isoindole-4,9-diones

AU - Deblander, Jurgen

AU - Abbaspour Tehrani, Kourosch

PY - 2008/6/22

Y1 - 2008/6/22

N2 - 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.

AB - 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.

KW - 2-azaanthraquinones

KW - napthalene

KW - ring closure

KW - napthoquinone

M3 - Meeting abstract (Book)

SP - 20

BT - 17th International Conference on Organic Synthesis (ICOS-17), June 22-27, 2008 Daejeon (Korea)

ER -

ID: 1715300