A REGIOSPECIFIC SYNTHESIS OF 2-AZAANTHRAQUINON-3-ONES VIA A HETERO-DIELS-ALDER REACTION WITH BROMONAPHTHOQUINONES

Authors
BOUAMMALI B PAUTET F FILLION H SOUFIAOUI M
Citation
B. Bouammali et al., A REGIOSPECIFIC SYNTHESIS OF 2-AZAANTHRAQUINON-3-ONES VIA A HETERO-DIELS-ALDER REACTION WITH BROMONAPHTHOQUINONES, Tetrahedron, 49(15), 1993, pp. 3125-3130
Citations number
13
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
15
Year of publication
1993
Pages
3125 - 3130
Database
ISI
SICI code
0040-4020(1993)49:15<3125:ARSO2V>2.0.ZU;2-L
Abstract
The Diels-Alder reaction between 2-azadienes and 2- or 3-bromo-5-subst ituted naphthoquinones (R3=OH, OAc, OMe) led to a regiospecific synthe sis of the corresponding 2-azaanthraquinon-3-ones. The results indicat e that the atom exerts a stronger regiochemical control in these cyclo additions than the 5-substituent.