3434
A. Alizadeh et al.
PAPER
IR (KBr): 3435 (OH), 1705 (NC=O), 1620 (C=O), 1566, 1438 (Ph),
1359, 1170 (SO2) cm-1.
Anal. Calcd for C27H24N2O5S (488.6): C, 66.38; H, 4.95; N, 5.73.
Found: C, 66.40; H, 5.00; N, 5.70.
1H NMR (500.1 MHz, CDCl3): d = 0.69-0.94 [br, 6 H,
N(CH2CH3)2], 3.42-3.52 [br, 4 H, N(CH2CH3)2], 5.56 (s, 1 H, OH),
7.14-7.98 (m, 15 H, 3 × C6H5).
3-Benzoyl-5-hydroxy-1-[(4-methylphenyl)sulfonyl]-5-phenyl-4-
(1-pyrrolidinyl)-1,5-dihydro-2H-pyrrol-2-one (2d)
Yield: 0.47 g (93%); pale-yellow powder; mp 155-157 °C.
13C NMR (125.7 MHz, CDCl3): d = 11.09 (NCH2CH3), 13.12
(NCH2CH3), 42.15 (NCH2CH3), 47.11 (NCH2CH3), 90.93 (COH),
98.90 (CCOC6H5), 126.10 (2 × CHortho of C6H5), 127.59 (2 × CHmeta
of C6H5), 128.33 (2 × CHortho of C6H5), 128.40 (2 × CHmeta of C6H5),
128.78 (2 × CHortho of C6H5), 129.10 (CHpara of C6H5), 130.10 (2 ×
CHmeta of C6H5), 132.99 (CHpara of C6H5), 133.13 (CHpara of C6H5),
137.28 (CipsoSO2), 138.28 (Cipso of COC6H5), 139.00 (Cipso of C6H5),
165.27 (CON), 165.73 (NC=C), 190.85 (COC6H5).
IR (KBr): 3410 (OH), 1700 (NC=O), 1621 (C=O), 1567, 1438 (Ph),
1347, 1162 (SO2) cm-1.
1H NMR (500.1 MHz, CDCl3): d = 1.59-1.81 (m, 4 H, CH2CH2),
2.29 (s, 3 H, CH3), 2.75 (br, 1 H, NCH2CH2), 2.90 (br, 1 H,
NCH2CH2), 3.39 (br, 1 H, NCH2CH2), 4.04 (br, 1 H, NCH2CH2),
5.55 (s, 1 H, OH), 6.94-7.97 (m, 14 H, Ar).
13C NMR (125.7 MHz, CDCl3): d = 21.52 (CH3), 24.88
(NCH2CH2), 25.30 (NCH2CH2), 49.91 (NCH2CH2), 54.53
(NCH2CH2), 90.85 (COH), 99.43 (CCOC6H5), 126.65 (2 × CHortho
of C6H5), 127.80 (2 × CHmeta of C6H5), 128.22 (2 × CHortho of C6H5),
128.66 (2 × CH of C6H4), 128.92 (2 × CH of C6H4), 129.13 (CHpara
of C6H5), 130.25 (2 × CHmeta of C6H5), 132.83 (CHpara of C6H5),
135.91 (CipsoSO2), 136.17 (Cipso of COC6H5), 138.65 (Cipso of C6H5),
144.21 (CipsoCH3), 164.81 (CON), 165.86 (NC=C), 189.86
(COC6H5).
MS: m/z (%) = 490 (3) [M+], 350 (4), 349 (13), 333 (12), 318 (4),
306 (4), 278 (3), 202 (5), 175 (4), 158 (4), 141 (7), 124 (4), 105
(100), 96 (4), 77 (94), 68 (13), 51 (15), 41 (4).
Anal. Calcd for C27H26N2O5S (490.6): C, 66.11; H, 5.34; N, 5.71.
Found: C, 66.10; H, 5.40; N, 5.70.
3-Benzoyl-4-(diethylamino)-5-hydroxy-1-[(4-methylphenyl)sul-
fonyl]-5-phenyl-1,5-dihydro-2H-pyrrol-2-one (2b)
Yield: 0.48 g (96%); pale-yellow powder; mp 174-176 °C.
MS: m/z (%) = 502 (1) [M+], 358 (1), 347 (1), 331 (6), 311 (1), 305
(18), 286 (1), 276 (9), 253 (2), 246 (1), 236 (2), 220 (1), 200 (21),
182 (1), 171 (13), 155 (20), 144 (1), 131 (5), 124 (3), 105 (100), 91
(67), 77 (86), 65 (22), 51 (19), 41 (11).
IR (KBr): 3425 (OH), 1698 (NC=O), 1624 (C=O), 1571, 1460 (Ph),
1355, 1166 (SO2) cm-1.
1H NMR (500.1 MHz, CDCl3): d = 0.76 [br, 6 H, N(CH2CH3)2],
2.29 (s, 3 H, CH3), 3.25 (br, 2 H, NCH2CH3), 3.49 (br, 2 H,
NCH2CH3), 5.63 (s, 1 H, OH), 6.93-7.95 (m, 14 H, Ar).
Anal. Calcd for C28H26N2O5S (502.6): C, 66.92; H, 5.21; N, 5.57.
Found: C, 66.90; H, 5.20; N, 5.50.
13C NMR (125.7 MHz, CDCl3): d = 12.10 [br, N(CH2CH3)2], 21.53
(CH3), 47.03 [br, N(CH2CH3)2], 90.95 (COH), 98.90 (CCOC6H5),
126.17 (2 × CHortho of C6H5), 127.79 (2 × CHmeta of C6H5), 128.37
(2 × CHortho of C6H5), 128.77 (2 × CH of C6H4), 128.92 (2 × CH of
C6H4), 129.05 (CHpara of C6H5), 130.11 (2 × CHmeta of C6H5),
132.95 (CHpara of C6H5), 136.13 (CipsoSO2), 137.43 (Cipso of
COC6H5), 138.35 (Cipso of C6H5), 144.18 (CipsoCH3), 165.42 (CON),
165.78 (NC=C), 190.87 (COC6H5).
MS: m/z (%) = 504 (2) [M+], 350 (3), 349 (11), 333 (12), 318 (3),
306 (4), 292 (1), 278 (2), 256 (1), 228 (2), 202 (4), 186 (1), 175 (4),
155 (6), 146 (2), 124 (4), 105 (100), 91 (39), 77 (51), 68 (14), 51
(13), 41 (3).
3-Benzoyl-5-hydroxy-5-phenyl-1-(phenylsulfonyl)-4-piperidi-
no-1,5-dihydro-2H-pyrrol-2-one (2e)
Yield: 0.49 g (97%); pale-yellow powder; mp 177-179 °C (Et2O).
IR (KBr): 3425 (OH), 1702 (NC=O), 1621 (C=O), 1580, 1439 (Ph),
1365, 1177 (SO2) cm-1.
1H NMR (500.1 MHz, CDCl3): d = 1.45-1.75 (m, 6 H, 3 × CH2),
3.16-3.27 (m, 4 H, 2 × NCH2), 5.76 (s, 1 H, OH), 7.14-7.98 (m, 15
H, 3 × C6H5).
13C NMR (125.7 MHz, CDCl3): d = 23.05 (NCH2CH2CH2), 25.23
(NCH2CH2CH2), 30.92 (NCH2CH2CH2), 44.92 (NCH2), 53.61
(NCH2), 90.85 (COH), 98.32 (CCOC6H5), 126.04 (2 × CHortho of
C6H5), 127.67 (2 × CHmeta of C6H5), 128.30 (2 × CHortho of C6H5),
128.38 (2 × CHmeta of C6H5), 128.75 (2 × CHortho of C6H5), 129.10
(CHpara of C6H5), 130.01 (2 × CHmeta of C6H5), 133.08 (CHpara of
C6H5), 133.12 (CHpara of C6H5), 137.27 (CipsoSO2), 138.45 (Cipso of
COC6H5), 139.11 (Cipso of C6H5), 165.48 (CON), 167.04 (NC=C),
191.32 (COC6H5).
Anal. Calcd for C28H28N2O5S (504.6): C, 66.65; H, 5.59; N, 5.55.
Found: C, 66.60; H, 5.60; N, 5.60.
3-Benzoyl-5-hydroxy-5-phenyl-1-(phenylsulfonyl)-4-(1-pyrro-
lidinyl)-1,5-dihydro-2H-pyrrol-2-one (2c)
Yield: 0.48 g (98%); pale-yellow powder; mp 138-140 °C.
MS: m/z (%) = 502 (1) [M+], 361 (14), 345 (16), 319 (2), 278 (2),
240 (7), 214 (4), 184 (3), 175 (4), 157 (2), 136 (4), 112 (7), 105
(100), 84 (65), 77 (89), 69 (16), 51 (14).
IR (KBr): 3440 (OH), 1701, 1677 (NC=O), 1616 (C=O), 1558,
1439 (Ph), 1359, 1198 (SO2) cm-1.
1H NMR (500.1 MHz, CDCl3): d = 1.59-1.85 (m, 4 H, CH2CH2),
2.76 (br, 1 H, NCH2CH2), 2.87 (br, 1 H, NCH2CH2), 3.38 (br, 1 H,
NCH2CH2), 4.03 (br, 1 H, NCH2CH2), 5.86 (s, 1 H, OH), 7.14-7.97
(m, 15 H, 3 × C6H5).
Anal. Calcd for C28H26N2O5S (502.6): C, 66.92; H, 5.21; N, 5.57.
Found: C, 66.90; H, 5.20; N, 5.50.
Crystal Data for 2e
13C NMR (125.7 MHz, CDCl3): d = 24.90 (NCH2CH2), 25.31
(NCH2CH2), 49.89 (NCH2CH2), 54.57 (NCH2CH2), 90.86 (COH),
99.32 (CCOC6H5), 126.63 (2 × CHortho of C6H5), 127.70 (2 × CHmeta
of C6H5), 128.27 (2 × CHortho of C6H5), 128.32 (2 × CHmeta of C6H5),
128.66 (2 × CHortho of C6H5), 129.17 (CHpara of C6H5), 130.26 (2 ×
CHmeta of C6H5), 132.93 (CHpara of C6H5), 133.16 (CHpara of C6H5),
135.79 (CipsoSO2), 138.54 (Cipso of C6H5CO), 139.09 (Cipso of C6H5),
164.95 (CON), 165.85 (NC=C), 189.98 (COC6H5).
C28H26N2O5S (CCDC 605973); MW = 502.6, monoclinic, space
group P21/c, a = 18.5261(8) Å, b = 11.2793(5) Å, c = 11.6832(5)
Å, b = 97.322(5)°, V = 2421.43(18) Å3, Z = 4, Dcalcd = 1.379 mg/m3,
F (000) = 1056, crystal dimension 0.07 × 0.10 × 0.25 mm, radiation,
Mo-Ka (l = 0.71073 Å), 1.11 £ 2q £ 27.00, intensity data were col-
lected at 295 K with a Bruker APEX area-detector diffractometer,
and employing w/2q scanning technique, in the range of –23 £ h £
23, -14 £ k £ 14, -14 £ l £ 14; the structure was solved by a direct
method, all non-hydrogen atoms were positioned and anisotropic
thermal parameters refined from 4348 observed reflections with
MS: m/z (%) = 488 (1) [M+], 347 (4), 331 (6), 305 (5), 276 (3), 226
(3), 200 (8), 183 (3), 172 (5), 157 (1), 141 (9), 131 (3), 122 (3), 105
(72), 91 (4), 77 (100), 69 (4), 51 (23), 41 (8).
Synthesis 2006, No. 20, 3431–3436 © Thieme Stuttgart · New York