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

✍ Scribed by José Marı́a Pérez; Pilar López-Alvarado; Carmen Avendaño; J.Carlos Menéndez

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
142 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

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-1azadienes 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.

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