Dimethyl Sulfoxide → 9-Cyano-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-bromo-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (530 mg, 1.50 mmol) and cuprous cyanide (890 mg, 9.9 mmol) in dimethyl sulfoxide (5 mL) was heated at 180° C. for 8.5 h and poured into 1N aqueous ammonium chloride (200 mL). The mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL). The extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL), dried over magnesium sulfate, and concentrated. The residue was rinsed with dichloromethane to give 176 mg of the title compound (39%): mp 255°~258° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.22 (bs, 1H), 7.47 (d, 1H, J=2 Hz), 7.31 (d, 1H, J=2 Hz), 5.02~5.16 (m, 1H), 3.63 (s, 3H), 2.95 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.85 (dm, 1H, J=17.1 Hz), 2.55~2.72 (m, 2H), 2.15 (dm, 1H, J=13.5 Hz), 1.80~1.98 (m, 1H).

Provenance & Evidence