6336-83-0Relevant academic research and scientific papers
EFFECT OF SRUCTURAL FACTORS ON THE FORMATION AND PROPERTIES OF ACYLAMINOANTHRAQUINONES
Kazankov, M. V.,Ginodman, L. G.,Mustafina, M. Ya.
, p. 306 - 313 (2007/10/02)
The N-methyl group prevents the acylation of α-aminoanthraquinones by acetic anhydride in the absence of acid catalysis.This is explained by hindrances for the abstraction of hydrogen atom from the 1-methylamino group, which is connected by an intramolecular hydrogen bond.Acid catalysis levels out the differences in the reactivity of the α-amino and α-methyl amino groups.The α-acetylamino groups have lower hydrolytic stability than the α-N-acetylmethylamino groups.These characteristics make it possible to realize a directed synthesis of acyl derivatives at theprimary or secondary α-amino groups of polyaminoanthraquinones.The introduction of acyl residues into the secondary α-amino groups completely excludes them conjugation with the anthraquinone ring, and an unexpectedly small hypsochromic shift of the absorption is observed in the 4-amino, 4-alkylamino, and particularly the 4-arylamino derivatives of 1-acylaminoanthraquinones.
