2872-47-1Relevant articles and documents
TRANSFORMATIONS OF ANTHRAISOXAZOL-6-ONES IN HYDROHALIC ACIDS
Gornostaev, L. M.,Sakilidi, V. T.
, p. 1112 - 1114 (1980)
4-Halo-1-aminoanthraquinones are formed when anthraisoxazol-6-ones are refluxed in hydrohalic acids.The 3 position undergoes halogenation when 5-substituted isoxazoles are used.The process takes place via a one-proton mechanism with the participation of halide ion in the rate-determining step, possibly with the intermediate formation of N-haloaminoanthraquinones.
Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones
Kargina,Gornostaev,Nefedov
, p. 70 - 77 (2013/03/28)
Heating of 6H-anthra[1,9-cd][1,2]oxazol-6-ones with dialkyl sulfoxides in sulfolane gave S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides which underwent cyclization to naphtho-[1,2,3-cd]indol-6(2H)-one derivatives on heating in boiling tetrahydrofuran in the presence of sodium methoxide. p-Toluenesulfinic acid was isolated as by-product in the cyclization of S-methyl-S-(4-methylphenyl)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) sulfoximide. The heterocyclizations of S,S-dipropyl- and S,S-dibutyl-N-(9,10- dioxo-9,10-dihydroanthracen-1-yl)sulfoximides to 1-ethyl- and 1-propylnaphtho[1,2,3-cd]-indol-6(2H)-ones were accompanied by formation of the corresponding 1-[1-hydroxyethyl(propyl)]naphtho-[1,2,3-cd]indol-6(2H)-ones.
EQUILIBRIUM NH ACIDITY OF 4-SUBSTITUTED 1-AMINOANTHRAQUINONES IN DIMETHYL SULFOXIDE
Os'kina, I. A.,Vlasov, V. M.,Terekhova, M. I.,Petrov, E. S.
, p. 2041 - 2044 (2007/10/02)
The equilibrium acidity of 1-amino-4-R-anthraquinones (R = CH3O, H, Cl, Br, NO2) was determined by transmetallation in DMSO (the Na+ cation, 25 deg C).A linear correlation was established between the pK values of the 4-substituted 1-aminoanthraquinones and the ?p- constants of the substituents R.The conduction of the electronic effect of the substituents R is stronger in the aminoanthraquinones than in the anilines and is closer to the naphthylamines.A linear relation is observed between the conduction of the electronic effect of the substituent and the square of the coefficient in the HOMO for the carbon atom at the point of addiion of the substituent in the series of anions of NH acids of various structure types.The increase in the NH acidity with change in the structure type of the NH acid is not necessarily accompanied by a decrease in the conduction of the electronic effect of the substituents.
The Schmidt reaction of anthraquinones
Flemming, Cecily A.,Gandhi, Sham S.,Gibson, Martin S.,Ruediger, Edward H.
, p. 624 - 628 (2007/10/02)
Schmidt reaction (sodium azide/sulfuric acid) of 1,5- and of 1,8-dichloroanthraquinones gives, in each case, both of the theoretically possible lactams (2,3,5,6-dibenzoazepin-4,7-diones).Two of the four theoretically possible lactams have been identified from Schmidt reaction of 1- and 2-chloroanthraquinones respectively.Methods used include:(a) preferential hydrolysis of one lactam and identification of the isomeric aminoanthraquinone formed on cyclodehydration of the resulting amino acid; (b) identification of the isomeric aminoanthraquinone(s) formed on direct treatment of a lactam (or mixture of lactams) by sulfuric acid; (c) cleavage by potassium tert-butoxide of the amino acid formed by preferential hydrolysis of one lactam and identification of the resulting benzoic acid as its methyl ester.