1-Naphthylamine → 9-Bromo-5-(1-naphthylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Participants

Reaction Steps

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (170 mg, 0.5 mmol) and 1-naphthylamine (150 mg, 1.05 mmol)to give 170 mg of the title compound (73%): mp 171°~172° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.06 (bs, 1H), 10.02 (s, 1H), 8.01~8.05 (m, 1H), 7.92~7.97 (m, 1H), 7.78 (d, 1H, J=7.9 Hz), 7.70 (d, 1H, J=6.9 Hz), 7.52~7.61 (m, 2H), 7.49 (d, 1H, J=7.6 Hz), 7.28 (s, 1H), 7.20 (s, 1H), 5.26~5.36 (m, 1H), 3.18 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.91 (dm, 1H, J=17.1 Hz), 2.73~2.85 (m, 2H), 2.17~2.29 (m, 1H), 1.89~2.09 (m, 1H).

Provenance & Evidence