S. Ke et al. / C. R. Chimie 14 (2011) 1071–1079
1077
DMSO-d6)
d
11.40 (bs, 1H, OH), 7.86 (q, 4J = 5.8 Hz,
1483, 1584, 1623, 1659, 2607, 2912, 3259, 3441 cmÀ1
;
1H
J = 8.9 Hz, 2H, Ph-H), 7.52 (s, 1H, NH), 7.25–7.06 (m, 7H,
Ph-H), 4.23 (t, J = 4.7 Hz, 1H, CH-N), 3.12 (q, J = 4.0 Hz, 1H,
CH2), 2.94 (q, J = 4.0 Hz, 1H, CH2); 13C NMR (100 MHz,
NMR (400 MHz, DMSO-d6) 11.28 (bs, 1H, OH), 7.74 (s, 1H,
d
NH), 7.61 (d, J = 2.1 Hz, 1H, Ph-H), 7.40 (q, 4J = 2.1 Hz,
J = 8.3 Hz, 1H, Ph-H), 7.27 (d, J = 8.3 Hz, 1H, Ph-H), 4.10 (t,
J = 4.6 Hz, 1H, CH-N), 2.12–1.69 (m, 7H, CH2CH2SCH3); ESI-
MS: calcd for C13H13Cl2NO2S m/z 317.0; found, 318.6
(M + H)+. Anal. Calcd for C13H13Cl2NO2S: C, 49.07; H, 4.12;
N, 4.40. Found: C, 49.15; H, 4.06; N, 4.44.
DMSO-d6):
d = 173.12, 170.20, 161.96, 136.84, 130.29,
129.40, 129.33, 128.47, 127.02, 115.17, 114.96, 103.96,
56.39, 37.73; ESI-MS: calcd for C17H14FNO2 m/z 283.1;
found, 284.7 (M + H)+. Anal. Calcd for C17H14FNO2: C,
72.07; H, 4.98; N, 4.94. Found: C, 72.01; H, 5.04; N, 4.88.
4.7.9. 7-Hydroxy-6-phenyl-2,3-dihydro-1H-pyrrolizin-
5(7aH)-one 12i
White powder, yield 68%, m.p. 212.0–214.0 8C; IR
(KBr pellet) nmax 632, 692, 787, 918, 941, 1230, 1304,
1340, 1572, 1650, 2560, 2896, 2975, 3443 cmÀ1; 1H NMR
4.7.4. 5-Benzyl-4-hydroxy-3-(4-methoxyphenyl)-1H-pyrrol-
2(5H)-one 12d
Yellow powder, yield 77%, m.p. 194.2–195.6 8C; IR (KBr
pellet) nmax 703, 736, 840, 1176, 1251, 1287, 1513, 1611,
1653, 2935, 3057, 3432 cmÀ1
;
1H NMR (400 MHz, DMSO-
(400 MHz, DMSO-d6) d 11.92 (bs, 1H, OH), 7.20-7.99 (m,
d6)
d
11.20 (bs, 1H, OH), 7.73 (d, J = 8.8 Hz, 2H, Ph-H), 7.47
5H, Ph-H), 4.19 (t, J = 6.4 Hz, 1H, CH-N), 1.40–3.09 (m,
6H, CH2CH2CH2); ESI-MS: calcd for C13H13NO2 m/z
215.1; found, 216.6 (M + H)+. Anal. Calcd for
(s, 1H, NH), 7.23–7.15 (m, 5H, Ph-H), 6.84 (d, J = 8.8 Hz, 2H,
Ph-H), 4.22 (t, J = 4.4 Hz, 1H, CH-N), 3.72 (s, 3H, CH3O), 3.11
(q, 2J = 13.7 Hz, J = 3.7 Hz, 1H, CH2), 2.93 (q, 2J = 13.7 Hz,
J = 5.8 Hz, 1H, CH2); ESI-MS: calcd for C18H17NO3 m/z
295.1; found, 296.8 (M + H)+. Anal. Calcd for C18H17NO3: C,
73.20; H, 5.80; N, 4.74. Found: C, 73.13; H, 5.86; N, 4.81.
C
13H13NO2: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.46;
H, 6.15; N, 6.43.
4.7.10. 6-(2,4-Dichlorophenyl)-7-hydroxy-2,3-dihydro-1H-
pyrrolizin-5(7aH)-one 12j
4.7.5. 4-Hydroxy-3,5-diphenyl-1H-pyrrol-2(5H)-one 12e
White powder, yield 78%, m.p. 191.4–192.5 8C; IR (KBr
pellet) nmax 692, 703, 775, 918, 1197, 1313, 1382, 1498,
White powder, yield 74%, m.p. 226.0–228.0 8C; IR (KBr
pellet) nmax 638, 772, 820, 870, 1099, 1221, 1367, 1340,
1578, 1608, 1653, 2685, 2887, 2949, 3441 cmÀ1 1H NMR
;
1593, 1659, 2578, 2943, 3069, 3411 cmÀ1
;
1H NMR
(400 MHz, DMSO-d6) d 11.78 (bs, 1H, OH), 7.60 (s, 1H, Ph-
(400 MHz, DMSO-d6)
d
11.25 (bs, 1H, OH), 8.01 (s, 1H,
H), 7.39 (q, 4J = 1.6 Hz, 3J = 8.4 Hz, 1H, Ph-H), 7.26 (d,
J = 8.4 Hz, 1H, Ph-H), 4.16 (t, J = 7.9 Hz, 1H, CH-N), 4.15-3.00
(m, 2H, CH2), 2.17–1.36 (m, 4H, CH2); ESI-MS: calcd for
NH), 7.95 (d, J = 7.2 Hz, 2H, Ph-H), 7.41–7.30 (m, 7H, Ph-H),
7.19 (t, J = 7.4 Hz, 1H, Ph-H), 5.03 (s, 1H, CH-N); ESI-MS:
calcd for C16H13NO2 m/z 251.1; found, 252.6 (M + H)+. Anal.
Calcd for C16H13NO2: C, 76.48; H, 5.21; N, 5.57. Found: C,
76.39; H, 5.27; N, 5.51.
C
13H11Cl2NO2 m/z 283.0; found, 284.6 (M + H)+. Anal. Calcd
for C13H11Cl2NO2: C, 54.95; H, 3.90; N, 4.93. Found: C,
55.03; H, 3.84; N, 4.85.
4.7.6. 3-(2,4-Dichlorophenyl)-4-hydroxy-5-phenyl-1H-
pyrrol-2(5H)-one 12f
4.7.11. 6-(4-Fluorophenyl)-7-hydroxy-2,3-dihydro-1H-
pyrrolizin-5(7aH)-one 12k
Light yellow powder, yield 68%, m.p. 195.2–196.7 8C; IR
(KBr pellet) nmax 697, 748, 828, 1099, 1191, 1322, 1382,
White powder, yield 76%, m.p. 228.6–230.2 8C; IR (KBr
pellet) nmax 644, 775, 834, 941, 1162, 1233, 1299, 1352,
1388, 1418, 1516, 1576, 1653, 2631, 2896, 2971,
; d 11.90 (bs,
3442 cmÀ1 1H NMR (400 MHz, DMSO-d6)
1480, 1581, 1626, 1659, 2515, 2920, 3290, 3437 cmÀ1 1H
;
NMR (400 MHz, DMSO-d6)
d
11.23 (bs, 1H, OH), 8.05 (s, 1H,
NH), 7.63 (s, 1H, Ph-H), 7.44–7.32 (m, 7H, Ph-H), 5.07 (s,
1H, CH-N); ESI-MS: calcd for C16H11Cl2NO2 m/z 319.0;
found, 320.6 (M + H)+. Anal. Calcd for C16H11Cl2NO2: C,
60.02; H, 3.46; N, 4.37. Found: C, 60.13; H, 3.56; N, 4.32.
1H, OH), 8.01 (q, 2H, Ph-H), 7.15 (t, J = 9.0 Hz, 2H, Ph-H),
4.14 (q, J = 8.4 Hz, 1H, CH-N), 3.41–3.02 (m, 2H, CH2),
2.20–1.33 (m, 4H, CH2); ESI-MS: calcd for C13H12FNO2 m/
z
C
233.1; found, 234.6 (M + H)+. Anal. Calcd for
13H12FNO2: C, 66.94; H, 5.19; N, 6.01. Found: C,
4.7.7. 3-(4-Fluorophenyl)-4-hydroxy-5-phenyl-1H-pyrrol-
2(5H)-one 12 g
66.87; H, 5.12; N, 6.07.
Light yellow powder, yield 64%, m.p. 179.2–180.5 8C; IR
(KBr pellet) nmax 576, 701, 784, 843, 1221, 1382, 1507,
4.7.12. 7-Hydroxy-6-o-tolyl-2,3-dihydro-1H-pyrrolizin-
5(7aH)-one 13a
1599, 1634, 1682, 2571, 2918, 3414 cmÀ1
;
1H NMR
White powder, yield 62%, m.p. 165.3–167.7 8C; IR (KBr
pellet) nmax 632, 724, 745, 781, 942, 1227, 1364, 1400,
(400 MHz, DMSO-d6)
d 11.35 (bs, 1H, OH), 8.05–8.01 (m,
3H, NH and Ph-H), 7.41–7.29 (m, 5H, Ph-H), 7.17 (t,
1590, 1611, 2673, 2890, 2965, 3437 cmÀ1 1H NMR
;
J = 9.0 Hz, 2H, Ph-H), 5.03 (s, 1H, CH-N); ESI-MS: calcd for
C
for C16H12FNO2: C, 71.37; H, 4.49; N, 5.20. Found: C, 71.32;
H, 4.56; N, 5.13.
(400 MHz, DMSO-d6) d 11.36 (bs, 1H, OH), 7.20–7.08 (m,
4H, Ph-H), 4.15 (q, J = 6.7 Hz, 1H, CH-N), 3.40–3.02 (m, 2H,
CH2), 2.19–1.38 (m, 7H, CH2 and CH3); 13C NMR
16H12FNO2 m/z 269.1; found, 270.6 (M + H)+. Anal. Calcd
(100 MHz, DMSO-d6):
d = 177.69, 172.54, 137.80,
131.45, 131.34, 130.22, 127.64, 125.69, 106.79, 63.93,
43.90, 29.28, 28.57, 20.41; ESI-MS: calcd for C14H15NO2
m/z 229.1; found, 230.6 (M + H)+. Anal. Calcd for
4.7.8. 3-(2,4-Dichlorophenyl)-4-hydroxy-5-(2-
(methylthio)ethyl)-1H-pyrrol-2(5H)-one 12 h
Light yellow powder, yield 65%, m.p. 185.0–186.0 8C; IR
(KBr pellet) nmax 671, 778, 825, 1099, 1200, 1316, 1409,
C
14H15NO2: C, 73.34; H, 6.59; N, 6.11. Found: C, 73.27;
H, 6.66; N, 6.03.