Reaktionsschritte
A mixture of 4-aminomethyl-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione hydrochloride (0.50 g, 1.6 mmol), 2-naphthyl isocyanate (0.26 g, 1.6 mmol), and diisopropylethylamine (0.40 g, 3.1 mmol) in 10 mL pyridine was warmed to 40° C. with stirring under N2, and the resulting solution was stirred at the same temperature for 2 hours. The mixture was cooled, and the solvent was evaporated under vacuum. The residue was chromatographed, eluting with 96:4 methylene chloride-methanol, to provide 0.46 g of the product in 70% yield: mp 201-203° C.; 1H NMR (DMSO-d6) δ 2.07-2.11 (m, 1H), 2.54-2.66 (m, 2H), 2.85-2.91 (m, 1H), 4.75 (d, J=6.0 Hz, 2H), 5.18 (dd, J=12.6 Hz, d=5.4 Hz, 1H), 6.88 (t, J=6.0 Hz, 1H), 7.28-7.34 (m, 1H), 7.38-7.45 (m, 2H), 7.70-7.88 (m, 6H), 8.05 (d, J=1.6 Hz, 1H), 9.05 (s, 1H), 11.20 (s, 1H); 13C NMR (DMSO-d6) δ 22.0, 31.0, 38.8, 48.9, 112.7, 119.4, 121.9, 123.6, 126.2, 126.8, 127.2, 127.4, 128.3, 128.8, 131.7, 133.8, 134.8, 137.9, 140.2, 155.3, 167.0, 167.6, 169.8, 172.8; Anal. calcd. for C25H20N4O5.0.5H2O: C, 64.51; H, 4.54; N, 12.03. Found: C, 64.87; H, 4.88; N, 11.59.
