Journal of Organic Chemistry p. 2285 - 2292 (1987)
Update date:2022-07-29
Topics:
Potts, Kevin T.
Walsh, Eileen B.
Bhattacharjee Debkumar
Azanaphthoquinones and 1-(dimethylamino)-3-methyl-1-azabuta-1,3-diene (methacrolein N,N-dimethylhydrazone) underwent extremely facile cycloaddition to aza- and polyazaanthraquinones after elimination of dimethylamine from the initial 1:1 cycloadduct and its subsequent oxidation.Introduction of a basic side chain into the 8-position of the azaanthraquinone occurred readily with primary amines and the 8-(tosyloxy) derivative, but more complex substitution patterns resulted with 5,8-bis(tosyloxy) derivatives and primary amines.
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