Heterocyclic quinones. VIII. Synthesis and spectra of new carbazoloquinone derivatives of naturally occurring amino acids

Fifteen naturally occurring amino acids representing basic, neutral and acidic members were interacted with 4,4′-dimethoxydiquinone (I). Basic amino acids reacted readily to give amino acid substituted carbazoloquinones (III), while neutral and acidic amino acids reacted only after addition of an acid binding agent. Using an excess of any of the amino acids resulted in the substitution of the quinonoid methoxyl group in compounds (III) by an amino acid moiety. In the case of basic amino acids, this substitution reaction was preferentially influenced by a terminal amino or guanidino amino rather than by an α-amino group. Moreover, basic amino acids could be reacted with two moles of (I) to produce dicarbazoloquinones (X). The i.r. and u.v.-visible spectra of the various carbazoloquinone products were determined and discussed.