Aniline → cis-9-Bromo-6-methyl-5-phenylcarbamoylmethyl-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 5 was carried out with cis-9-bromo-5-carboxymethyl-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (100 mg, 0.283 mmol) and aniline (28 μL, 0.311 mmol) to give 108 mg of the title compound (89%): mp>300° C.; 1H NMR (270 MHz, DMSO-d6) δ12.03 (s, 1H), 9.89 (s, 1H), 7.45 (d, 2H, J=7.6 Hz), 7.27 (t, 2H, J=7.6 Hz), 7.19 (d, 1H, J=2 Hz), 7.17 (d, 1H, J=2 Hz), 7.02 (t, 1H, J=7.6 Hz), 5.16~5.26 (m, 1H), 2.70~2.85 (m, 2H), 2.63 (dd, 1H, J=14.2, 5.9 Hz), 2.24 (dd, 1H, J=14.2, 6.6 Hz), 2.10~2.26 (m, 1H), 1.13 (d, 3H, J=6.9 Hz).

Provenance & Evidence