Hetero Diels–Alder Reactions of 1-Acetylamino- and 1-Dimethylamino-1-azadienes with Benzoquinones

Treatment of bromobenzoquinone with 2 equiv. of a 1-dimethylamino-1-azadiene afforded mixtures of the corresponding 1,8-diaza-9,10-anthraquinone and 1,5-diaza-9,10-anthraquinone. Double hetero Diels–Alder reactions between 1-dimethylamino-1-azadienes and 2,6-dibromobenzoquinone afford symmetrically...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2000-03, Vol.56 (11), p.1561-1567
Main Authors: Pérez, José Marı́a, López-Alvarado, Pilar, Avendaño, Carmen, Menéndez, J.Carlos
Format: Article
Language:English
Subjects:
benzoquinones
Diels–Alder reactions
quinolines
quinones
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Treatment of bromobenzoquinone with 2 equiv. of a 1-dimethylamino-1-azadiene afforded mixtures of the corresponding 1,8-diaza-9,10-anthraquinone and 1,5-diaza-9,10-anthraquinone. Double hetero Diels–Alder reactions between 1-dimethylamino-1-azadienes and 2,6-dibromobenzoquinone afford symmetrically substituted 1,8-diaza-9,10-anthraquinone derivatives in excellent yields. 3-Substituted 1-azadienes afford aromatic derivatives, while 4-substituted or 3,4-disubstituted 1-azadienes lead to 1,8-bis-(dimethylamino)-1,4,5,8-tetrahydro-1,8-diaza-9,10-anthraquinones, which were aromatized under thermal conditions. The hetero Diels–Alder reactions could also be controlled to give isolated 7-bromo-5,8-quinolinequinones, whose treatment with a second azadiene allowed the preparation of unsymmetrical 1,8-diaza-9,10-anthraquinones.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00058-2