E. Conchon et al. / Tetrahedron 62 (2006) 11136–11144
11141
4.4.9. 4-(5-Methyl-1H-indol-3-yl)-1H-5-hydroxy-2,5-di-
hydro-pyrrol-2-one (5b). Off-white solid. Mp 104 ꢀC. IR
(KBr) nC]C 1615 cmꢁ1, nC]O 1682 cmꢁ1, nNH 3274,
.
C13H12N2O2Na 251.0796, found 251.0805.
4.4.13. 4-(5-Benzyloxy-1H-indol-3-yl)-1H-5-hydroxy-2,5-
dihydro-pyrrol-2-one (5c). Off-white solid. Mp 215–
216 ꢀC. IR (KBr) nC]C 1613 cmꢁ1, nC]O 1681 cmꢁ1
,
3398 cmꢁ1
HRMS (ESI+) [M+Na]+ calcd for
nNH,OH 3040–3663 cmꢁ1. HRMS (ESI+) [M+H]+ calcd for
C19H17N2O3 321.1239, found 321.1242.
1H NMR (400 MHz, DMSO-d6): 2.47 (3H, s), 5.83 (1H, dd,
J1¼9.5 Hz, J2¼1.5 Hz), 6.21 (1H, d, J¼1.0 Hz, H3), 6.23
(1H, d, J¼9.5 Hz), 7.05 (1H, dd, J1¼8.0 Hz, J2¼1.0 Hz),
7.39 (1H, d, J¼8.0 Hz), 7.70 (1H, br s), 7.82 (1H, d,
J¼2.5 Hz), 8.16 (1H, s, NH), 11.59 (1H, s, NH).
13C NMR (100 MHz, DMSO-d6): 21.2 (CH3), 80.5 (CHOH),
107.6, 125.6, 129.4, 134.9, 154.5 (C quat), 111.7, 113.0,
119.8, 123.6, 128.4 (C tert), 172.9 (C]O).
1H NMR (400 MHz, DMSO-d6): 5.23 (2H, s), 5.81 (1H, d,
J¼9.5 Hz), 6.22 (1H, s), 6.23 (1H, d, J¼9.0 Hz), 6.95 (1H,
d, J¼9.0 Hz), 7.34–7.46 (5H, m), 7.54 (2H, d, J¼7.5 Hz),
7.83 (1H, s), 8.17 (1H, s), 11.61 (1H, s, NH).
13C NMR (100 MHz, DMSO-d6): 69.7 (CH2OBn), 80.5
(CHOH), 103.5, 111.4, 111.9, 112.8, 127.6 (3C), 128.3
(2C), 129.0 (C tert), 107.9, 125.8, 131.7, 137.7, 153.6,
154.3 (C quat), 173.0 (C]O).
4.4.10. 4-(5-Methyl-1H-indol-3-yl)-1H-2,5-dihydro-pyr-
rol-2-one (6b). Off-white solid. Mp 140 ꢀC. IR (KBr)
4.4.14. 4-(5-Benzyloxy-1H-indol-3-yl)-1H-2,5-dihydro-
pyrrol-2-one (6c). Off-white solid. Mp 235–237 ꢀC. IR
(KBr) nC]C 1606 cmꢁ1, nC]O 1651 cmꢁ1, nNH 3200–
3430 cmꢁ1. HRMS (ESI+) [M+H]+ calcd for C19H17N2O2
305.1290, found 305.1297.
nC]C 1605 cmꢁ1, nC]O 1649 cmꢁ1, nNH 3035–3430 cmꢁ1
.
HRMS (ESI+) [M+H]+ calcd for C13H13N2O 213.1028,
found 213.1027.
1H NMR (400 MHz, DMSO-d6): 2.46 (3H, s), 4.43 (2H, s),
6.28 (1H, d, J¼1.0 Hz, H3), 7.05 (1H, dd, J1¼8.0 Hz,
J2¼1.0 Hz), 7.37 (1H, d, J¼8.0 Hz), 7.69 (1H, s), 7.81
(1H, s), 7.82 (1H, s), 11.58 (1H, s, NH).
1H NMR (400 MHz, DMSO-d6): 4.41 (2H, s), 5.23 (2H, s),
6.29 (1H, s, H3), 6.94 (1H, d, J¼9.0 Hz), 7.34–7.46 (5H, m),
7.54 (2H, d, J¼7.5 Hz), 7.82 (2H, s), 11.59 (1H, s, NH).
13C NMR (100 MHz, DMSO-d6): 48.3, 69.7 (CH2), 103.2,
103.5, 112.9, 104.0, 114.0, 127.2, 127.6 (2C), 128.3 (2C),
129.0 (C tert), 108.9, 125.3, 132.0, 137.7, 152.7, 153.6 (C
quat), 175.2 (CO).
13C NMR (100 MHz, DMSO-d6): 21.2 (CH3), 48.3 (CH2N),
108.6, 125.1, 129.4, 135.1, 152.8 (C quat), 111.8, 114.1,
119.6, 123.6, 126.7 (C tert), 175.1 (C]O).
4.4.11. 3-(5-Benzyloxy-1H-indol-3-yl)-1H-5-hydroxy-2,5-
dihydro-pyrrol-2-one (3c). Off-white solid. Mp >200 ꢀC
4.4.15. 4-(5-Hydroxy-1H-indol-3-yl)-1H-5-hydroxy-2,5-
dihydro-pyrrol-2-one (5d). Brown solid. Mp 102–104 ꢀC.
IR (KBr) nC]C 1614 cmꢁ1, nC]O 1678 cmꢁ1, nNH,OH
2981–3599 cmꢁ1. HRMS (ESI+) [M+Na]+ calcd for
C12H10N2O3Na 253.0589, found 253.0595.
(decomposition). IR (KBr) nC]C 1631 cmꢁ1
, nC]O
1706 cmꢁ1
, . HRMS (ESI+)
nNH,OH 3100–3500 cmꢁ1
[M+H]+ calcd for C19H17N2O3 321.1239, found 321.1256.
1H NMR (400 MHz, DMSO-d6): 5.22 (2H, s, CH2), 5.58
(1H, dt, J1¼9.0 Hz, J2¼2.0 Hz, H5), 5.98 (1H, d,
J¼9.0 Hz, OH), 6.94 (1H, dd, J1¼9.0 Hz, J2¼2.0 Hz),
7.12 (1H, t, J¼1.5 Hz), 7.36–7.46 (5H, m), 7.55 (2H, d,
J¼7.0 Hz), 8.25 (1H, d, J¼3.0 Hz), 8.63 (1H, s, NH),
11.33 (1H, d, J¼2.5 Hz, NH).
13C NMR (100 MHz, DMSO-d6): 69.9 (CH2O), 78.3
(CHOH), 103.4, 112.3, 112.6, 127.1, 127.6 (3C), 128.3
(2C), 133.5 (C tert), 105.9, 125.9, 130.6, 131.3, 137.8,
153.2 (C quat), 171.8 (C]O).
1H NMR (400 MHz, DMSO-d6): 5.81 (1H, d, J¼10.0 Hz),
5.93 (1H, s), 6.23 (1H, d, J¼10.0 Hz, OH), 6.75 (1H, d,
J¼9.0 Hz), 7.14 (1H, s), 7.31 (1H, dd, J1¼9.0 Hz,
J2¼1.0 Hz), 7.78 (1H, s), 8.16 (1H, s), 8.97 (1H, s), 11.49
(1H, s, NHindole).
13C NMR (100 MHz, DMSO-d6): 80.5 (CHOH), 104.2,
111.9, 112.0, 112.6, 128.8 (C tert), 107.2, 126.3, 130.9,
152.1, 154.9 (C quat), 172.8 (C]O).
4.4.16. 3-(5-Hydroxy-1H-indol-3-yl)-1H-2,5-dihydro-
pyrrol-2-one (4d). Brown solid. Mp 180 ꢀC. IR (KBr)
4.4.12. 3-(5-Benzyloxy-1H-indol-3-yl)-1H-2,5-dihydro-
pyrrol-2-one (4c). Brown solid. Mp 185 ꢀC. IR (KBr)
nC]C 1618 cmꢁ1, nC]O 1672 cmꢁ1, nNH 3100–3550 cmꢁ1
.
Mass (APCI+) [M+H]+ 215.
nC]C 1620 cmꢁ1, nC]O 1680 cmꢁ1, nNH 3100–3500 cmꢁ1
.
Mass (ESI+) [M+K]+ 343, [M+Na]+ 327.
1H NMR (400 MHz, DMSO-d6): 4.04 (2H, s), 6.72 (1H, d,
J¼9.0 Hz), 7.20 (1H, s), 7.21 (1H, s), 7.27 (1H, d,
J¼9.0 Hz), 8.18 (1H, s), 8.39 (1H, s), 8.84 (1H, br s),
11.08 (1H, s, NH).
1H NMR (400 MHz, DMSO-d6): 4.05 (2H, s), 5.20 (2H, s),
6.92 (1H, dd, J1¼9.0 Hz, J2¼2.0 Hz), 7.33–7.47 (6H, m),
7.54 (2H, d, J¼7.5 Hz), 8.23 (1H, d, J¼2.5 Hz), 8.41 (1H,
s, NH), 11.22 (1H, s, NH).
13C NMR (100 MHz, DMSO-d6): 45.9 (CH2), 103.9, 111.6,
112.1, 125.8, 130.5 (C tert), 106.0, 126.3, 130.4, 131.0,
151.4 (C quat), 173.2 (C]O).
13C NMR (100 MHz, DMSO-d6): 46.0 (CH2N), 69.9
(CH2OBn), 103.4, 112.0, 112.4, 126.1, 127.6, 127.7 (2C),
128.3 (3C), 131.3 (C tert), 106.7, 125.8, 130.6, 131.2,
137.8, 153.0 (C quat), 173.1 (C]O).
4.4.17. 2H,5H,7H-1,3,4,6-Tetrahydro-dipyrrolo[3,4-
a:3,4-c]carbazole-1,4,6-trione (7). A mixture of maleimide