1-Amino-4-arylaminoanthraquinones (II) have been prepared in high yields by reacting 1-amino-4-chloroanthraquinone (Ia, 1 mol) with arylamines (6 mol) and anhyd.AlCl3 (5 mol) in nitrobenzene at room temperature. 1-Amino-2-bromoanthraquinone, 2-amino-1-chloroanthraquinone, 1-benzamido-4-chloroanthraquinone and 1-amino-5-chloroanthraquinone fail to give arylaminated products. 1-Amino-2,4-dibromoanthraquinone (Ic) gives only 4-arylaminated compounds (IIq-s) whereas 1-amino-8-chloroanthraquinone (Ie) gives 2-arylaminated derivatives (III).A plausible mechanism for the reaction has been suggested.The arylaminated compounds have been applied on polyester as disperse dyes and their dyeing properties evaluated.
Philip, George,Nabar, U. T.,Kanetkar, V. R.,Sunthankar, S. V.
p. 808 - 811
(2007/10/02)
INSERTION OF 1-NITRENOANTRAQUINONES AT C-H BOND
The thermolysis of anthraoxazol-6-ones in cumene and p-cymene leads to insertion of the obtained nitrene at the C-H bond and also to reduction of the nitrene to a primary amine.
Gornostaev, L. M.,Es'kin, A. P.,Korniets, E. D.
p. 2093 - 2096
(2007/10/02)
AMINATION OF ANTHRAISOXAZOL-6-ONES
The behavior of 3,5-dihalo derivatives of anthraisoxazol-6-one with respect to primary and secondary amines was studied. 5-Chloroanthraisoxazol-6-one undergoes amination particularly readily.The products of the reaction of isoxazoles with amines are the corresponding amino derivatives.The amination of 5-chloroanthraisoxazol-6-one in refluxing dimethylformamide (DMF) is accompanied by reductive cleavage of the isoxazole ring and the formation of 1-amino-4-arylaminoanthraquinones.Amination in the 5 position with substitution of a hydride ion takes place primarily in the reaction of 3-chloroanthraisoxazol-6-one with benzylamine or cyclohexylamine, whereas the chlorine in the 3 position is replaced by the action of morpholine or piperidine on the same substrate.
Gornostaev, L. M.,Zeibert, G. F.,Zolotareva, G. I.
p. 704 - 707
(2007/10/02)
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