Synthesis of 1-aminoanthrapyridones and their derivatives

Synthesis of 4-alkyl-3,4-dihydronaphtho[2,3-f]quinoxaline-2,7,12-(1H)-triones and 3-alkyl-5-arylamino-2-chloromethyl-3H-anthra[1,2-d]imidazole-6,11-diones based on reactions of 1-amino-9,10-anthraquinones with chloroacetyl chloride

“…The 1 H NMR spectra were recorded on a Bruker DRX in strument (500 MHz) in DMSO d 6 with Me 4 Si as the internal standard. The molecular weights of the reaction products were confirmed by mass spectrometry on a Finnigan MAT 8200 in strument.…”

“…241-243 °C. 1 2 Benzylamino 4 (4 methylphenyl)amino 1 chloroacetylami no 9,10 anthraquinone (7b). Compound 6b (0.87 g, 0.002 mol) was kept in anhydrous diethyl ether (30 mL) with chloroacetyl chloride (0.34 g, 0.003 mol) for 30 min.…”

“…214-215 °C. 1 3 Benzyl 2 chloromethyl 5 (4 methylphenyl)amino 3H an thra [1,2 d]imidazole 6,11 dione (8b). The synthesis was carried out analogously to that described above starting from 6b (1 g, 0.0023 mol).…”

“…185-186 °C. 1 2 Bromo 1 chloroacetylamino 4 (4 methylphenyl)amino 9,10 anthraquinone (9b). 1 Amino 2 bromo 4 (4 methylphenyl) amino 9,10 anthraquinone 7 (6.1 g, 0.015 mol) was refluxed in benzene (80 mL) with chloroacetyl chloride (6 mL) for 3 h. The precipitate that formed after cooling was filtered off, washed with benzene and Et 2 O, and purified by recrystalliza tion from o xylene.…”

“…198-199 °C. 1 Compound 9a (0.67 g, 0.002 mol) was dissolved in dioxane (10 mL). Then benzylamine (1 mL) was added.…”