Selective butylamination promoted by copper salts was observed on the reaction of 5,8-dihydroxy-1,4-naphthoquinone(DHNQ) with butylamine. A novel β-butylamination of DHNQ proceeded in the presence of copper salts. A number of β-butylaminated naphthoquinone derivatives were conveniently obtained.

The synthesis of 13-membered polyamine alkaloid, (S)-dihydroperiphylline, was achieved by the condensation of a chiral β-lactam, (S)-4-phenyl-2-azetidinone, with a cyclic imino ether of a 9-membered lactam, followed by reductive ring expansion. Both of these reactions proceeded with retention of configuration around the chiral center to give the optical pure 13-membered alkaloids.

The reaction of 1,4-dihydroxyanthraquinone with ethylenediamine in the presence of Cu(I)Cl or Cu(II)Cl2 gave 6-hydroxy-1,2,3,4-tetrahydronaphtho- (2, 3-f) -quinoxaline- 7,12-dione in quantitative yield at ambient temperature. The reaction was promoted greatly by copper ions. The possible mechanism and the role of copper ions were discussed.

The reaction of 1-amino-4-acylaminoanthraquinones with piperidine in the presence of CoCl2 and atmospheric oxygen gave the 2-aminated products in 75–80%, and similar reaction of 1-hydroxyanthraquinone or 1-aminoanthraquinone-2-sulfonic acid with butylamine gave the corresponding 4-aminated products, respectively. The effects of the α-substituents and the role of metal salts were discussed.

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