SOME EXPERIMENTS WITH AMINODIHYDROXYANTHRAQUINONES

Article abstract of DOI:10.1016/S0040-4020(01)87394-4

4-Amino-1-hydroxy-8-methoxyanthraquinone has been synthesized and alkylated with 1-nitropropane to give a mixture of 2- and 3-propyl compounds. Leuco-5-hydroxyquinizarin regioselectively reacts with n-propylamine and benzylamine to give 4-imino compounds, which are shown by (14)N n.m.r. spectroscopy to exist in solution as zwitterions. The benzylamine is regioselectively alkylated with propanal to give 4-benzylamino-1,5-dihydroxy-2-propylanthraquinone.