p-Toluenesulfonic acid → 3,3a-Dihydropyrrolo[1,2-a]quinoxaline-1,4(2H,5H)-dione

反応式

C[O:2][C:3](=O)[CH:4]([CH2:15][CH2:16][C:17]([O:19]C)=O)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.[Pd]>[C:17]1(=[O:19])[N:5]2[C:6]3[C:7]([NH:12][C:3](=[O:2])[CH:4]2[CH2:15][CH2:16]1)=[CH:8][CH:9]=[CH:10][CH:11]=3

参加物

実験手順

To N-(2-nitrophenyl)-DL-glutamic acid dimethyl ester (XI, EXAMPLE 279, 5.09 g) in methanol (150 ml) is added p-toluenesulfonic acid (0.158 g) and palladium on carbon (10%, 0.495 g). The mixture is shaken under hydrogen at 37 psi for 2 hr; the mixture is then filtered and the tiltrate is concentrated to about 70 ml. Additional p-toluenesulfonic acid (0.15 g) is added, and the solution is heated at 60° for 1 hr. After cooling, the solid is collected, washed with methanol, and dried to give the title compound, mp 231°-232°; NMR (CDCl3) 2.65, 4.41, 6.93, 7.14, 8.10 and 8.55 δ.