152190-64-2Relevant academic research and scientific papers
REACTION OF α-HALOGENO- AND α-NITROANTHRAQUINONES WITH THE ANIONS OF CH ACIDS. I. SYNTHESES OF 1-ALKYL-, 1,5-DIALKYL-, AND 1-AROYLANTHRAQUINONES
Gorelik, M. V.,Titova, S. P.,Kanor, M. A.
, p. 1852 - 1857 (2007/10/02)
The reaction of 1-halogeno- and 1-nitroanthraquinones with cyanoacetic and phenylsulfonylacetic esters, phenylacetonitrile, malonic ester, and nitromethane in a polar aprotic solvent in the presence of a base leads to the corresponding 1-alkylanthraquinones, while the reaction of 1,5-dichloro- and 1,5-dinitroanthraquinones leads to 5-chloro- and 5-nitro-1-alkylanthraquinones or 1,5-bisalkylanthraquinones, depending on the conditions.In the presence of the base the products are alkylated at the carbon atom adjacent to the anthraquinone ring, after which the ethoxycarbonyl group at the quaternary carbon atom is easily eliminated in the alkaline medium. 1-(phenylcyanomethyl)anthraquinone is oxidized by oxygen in an alkaline medium to 1-benzoylanthraquinone.
