Conclusions
5-Hydroxy-2-aryl- and 5-hydroxy-2-alkylamino-N-aryl-1,4-naphthoquinon-4-imines react with primary aliphatic amines to form previously unavailable 5-hydroxy-2-aryl- and 5-hydroxy-2-alkylamino-N-alkyl-1,4-naphthoquinon-4-imines by nucleophilic substitution of the N-arylimino group by an alkylamine residue. The product of the amination of the second ring was isolated among other products upon an increase in the reaction time. This is probably a consequence of the existence of 5-hydroxy-1,4-naphthoquinonimines in the 4-amino-1,5-naph-thoquinone tautomeric form.
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Literature cited
L. V. Éktova and E. P. Fokin, Zh. Org. Khim.,20, 805 (1984).
L. V. Éktova, R. P. Shishkina, and E. P. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1351 (1987).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1672–1676, July, 1988.
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Éktova, L.V., Shishkina, R.P. & Fokin, E.P. Reaction of 5-hydroxy-n-aryl-1,4-naphthoquinon-4-imines with primary aliphatic amines. Russ Chem Bull 37, 1487–1490 (1988). https://doi.org/10.1007/BF00962769
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DOI: https://doi.org/10.1007/BF00962769