Amino acid derivatives of 2-chloro-N-(9,10-dioxy-9,10-dihydroanthracen-1-yl)acetamide

Notwithstanding the well studied 9,10-anthraquinone chemistry many its derivatives are poorly understood up till now. Among them are, in particular, the derivatives of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide (I) [1–5]. We carried out reactions of compound I with various amino acids: glycine, alanine, phenylalanine, valine, leucine, and methionine IIa–IIf in the presence of potassium carbonate in DMSO at heating. Target products IIIa–IIIf were isolated from the reaction mixture diluting the latter with 5-fold volume of water followed by acidifying with dilute hydrochloric acid. The separated solid precipitate was fi ltered off and purifi ed by recrystallization from a mixture acetonitrile– water, 1 : 5. {2-[(9,10-Dioxy-9,10-dihydroanthracen-1-yl)amino]-2-oxoethyl}glycine (IIIa). Yield 54%, mp 196°С. IR spectrum, ν, cm–1: 3425 (CH2NH), 3345 (NHСО), 3000–2500 (COОН), 1720 (С=О in COOH), 1680, 1631 (С=О quinoid ring), 1645 (СОNH). 1Н NMR spectrum, δ, ppm: 12.66 s (1H, OH), 10.72 s (1H, NH), 8.94 d (1Harom, J 7.7 Hz), 8.14–8.21 m (3Harom), 7.91 m