REACTIONS OF 4-DIALKYLAMINO-5-METHOXY-1,2-BENZOQUINONES IN ACIDIC MEDIA - SELECTIVE C-ALKYLATION OR N-DEALKYLATION

-(N-methyl-alkylamino)-5-methoxy-1,2-benzoquinones 3, for which N-alky l group R(1) can give rise to a stabilized carbonium ion, undergo sele ctive acid-catalyzed rearrangements to 3-alkylated-1,2-benzoquinones 4 . Aziridino-quinone 10c gives rise to the heterobicyclic 1,2-benzoquin one 11. When R(1) does not contain groups capable of stabilizing a pos itive charge, efficient and selective N-dealkylations occur. The mecha nisms of these reactions are discussed. Copyright (C) 1996 Published b y Elsevier Science Ltd