18969-93-2Relevant articles and documents
PERI-NAPHTHYLENE DIAMINES III. CONVENIENT METHOD FOR THE ALKYLATION OF 1,8-NAPHTHYLENEDIAMINES AND PERIMIDINES
Kurasov, L. A.,Posharskii, A. F.,Kuz'menko, V. V.
, p. 1735 - 1738 (2007/10/02)
In dimethyl sulfoxide or hexamethylphosphorotriamide in the presence of potassium hydroxide 1,8-naphthylenediamine is readily alkylated by an excess of methyl and ethyl iodide to the corresponding 1,8-bis(dialkylamino)naphthalene.Perimidone, which has low basicity, is methylated to 1,3-dimethylperimidone under these conditions.The potassium hydroxide-dimethyl sulfoxide system also secures higher yields of the N-substituted products during the alkylation of perimidine, 2-methylperimidine, and aceperimidine by alkyl halides compared with the potassium hydroxide-alcoholsystem.The yield and structure of the products from benzylation of the perimidines depend on the presence of substituents at position 2 of the heterocyclic system of perimidine.