N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[4-(4-methylphen-
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[5-(4-methylphen-
yl)-2-thienyl]acrylic acid amide (11b)
yl)-2-thienyl]acrylic acid amide (12b)
From 3-[4-(4-methylphenyl)-2-thienyl]acrylic acid (219 mg, 0.9
mmol) according to general procedure 3. Purification: recrystalliza-
tion from toluene. Yield: 367 mg (72%). Mp 218°C. IR (KBr): ν ϭ
From N-[3-benzoyl-4-(4-tolylacetylamino)phenyl]-3-(5-bromo-2-thi-
enyl)acrylic acid amide 15 (440 mg, 0.75 mmol) according to general
procedure 1. Purification: column chromatography with dichloro-
methane to wash out side products and EtOAc to elute the product.
Yield: 286 mg (67%). Mp 204°C. IR (KBr): ν ϭ 3388, 3296, 3029,
3371, 1677, 1653, 1631, 1554, 1508, 1402 cmϪ1 1H NMR (DMSO
.
d6): δ 2.20 (s, 3H), 2.27 (s, 3H), 3.30 (s, 2H), 6.50 (d, J ϭ 16 Hz, 1H),
6.94 (m, 2H), 7.00 (s, 2H), 7.18 (s, 2H), 7.45 (m, 2H), 7.51Ϫ7.61 (m,
4H), 7.64 (m, 2H), 7.71 (m, 2H), 7.79 (m, 1H), 7.82 (m, 2H), 10.06
(s, 1H), 10.29 (s, 1H). MS (EI): m/z ϭ 43 (100), 55 (91), 69 (56), 83
(35), 256 (29), 570 (7) Mϩ. Anal. calcd for C36H30N2O3S: C, 75.76;
H, 5.30; N, 4.91; S, 5.62; found: C, 75.41; H, 5.25; N, 4.94; S, 5.84.
1642, 1614, 1498 cmϪ1 1H NMR (DMSO d6): δ 2.18 (s, 3H), 2.31
.
(s, 3H), 3.27 (s, 2H), 6.44 (d, J ϭ 16 Hz, 1H), 6.92 (m, 4H), 7.13
(m, 2H), 7.23 (m, 2H), 7.27Ϫ7.36 (m, 5H), 7.42 (m, 2H), 7.54 (m,
2H), 7.61 (d, J ϭ 16 Hz, 1H), 7.89 (m, 1H), 10.11 (s, 1H), 11.93 (s,
1H). MS (EI): m/z ϭ 44 (81), 227 (100), 326 (64), 552 (42), 570 (0.3)
Mϩ. Anal. calcd for C36H30N2O3S: C, 75.76; H, 5.30; N, 4.91; S,
5.62; found: C, 75.93; H, 5.36; N, 5.02; S, 5.68.
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[4-(4-trifluoro-
methylphenyl)-2-thienyl]acrylic acid amide (11c)
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[5-(4-trifluoro-
methylphenyl)-2-thienyl]acrylic acid amide (12c)
From 3-[4-(4-trifluoromethylphenyl)-2-thienyl]acrylic acid (289 mg,
1 mmol) according to general procedure 3. Purification: recrystalli-
zation from ethanol. Yield: 360 mg (58%). Mp 179°C. IR (KBr):
From 3-[5-(4-trifluoromethylphenyl)-2-thienyl]acrylic acid (86 mg,
0.3 mmol) according to general procedure 3. Purification: recrystal-
lization from toluene. Yield: 73 mg (35%). Mp 240°C. IR (KBr):
ν ϭ 3347, 1672, 1653, 1617, 1559, 1507, 1327 cmϪ1 1H NMR
.
(DMSO d6): δ 2.25 (s, 3H), 3.35 (s, 2H), 6.59 (d, J ϭ 16 Hz, 1H),
6.98 (m, 2H), 7.04 (m, 2H), 7.49 (m, 2H), 5.57 (m, 1H), 7.64 (m,
1H), 7.68 (m, 2H), 7.73Ϫ7.79 (m, 4H), 7.87 (m, 1H), 7.94 (m, 3H),
8.15 (m, 1H), 10.11 (s, 1H), 10.36 (s, 1H). MS (EI): m/z ϭ 212
(56), 281 (80), 344 (59), 492 (45), 624 (100) Mϩ. Anal. calcd for
C36H27F3N2O3S: C, 69.22; H, 4.36; N, 4.48; S, 5.13; found: C, 69.07;
H, 4.47; N, 4.59; S, 5.27.
ν ϭ 3242, 1662, 1614, 1540, 1509, 1327 cmϪ1 1H NMR (DMSO
.
d6): δ 2.25 (s, 3H), 3.35 (s, 2H), 6.58 (d, J ϭ 16 Hz, 1H), 6.98 (m,
2H), 7.04(m, 2H), 7.49 (m, 3H), 7.56 (m, 1H), 7.63 (m, 1H), 7.69
(m, 3H), 7.73 m, 1H), 7.76 (m, 2H), 7.79 (m, 1H), 7.87 (m, 1H),
7.91 (m, 2H), 10.11 (s, 1H), 10.39 (s, 1H). MS (EI): m/z ϭ 281
(100), 326 (95), 344 (20), 607 (22), 624 (30) Mϩ. Anal. calcd for
C36H27F3N2O3S: C, 69.22; H, 4.36; N, 4.48; S, 5.13; found: C, 69.07;
H, 4.47; N, 4.59; S, 5.36.
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[4-(4-methoxyphen-
yl)-2-thienyl]acrylic acid amide (11d)
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[5-(4-methoxy-
phenyl)-2-thienyl]acrylic acid amide (12d)
From 3-[4-(4-methoxyphenyl)-2-thienyl]acrylic acid (260 mg,
mmol) according to general procedure 3. Purification: recrystalliza-
1
tion from toluene. Yield: 328 mg (56%). Mp 182°C. IR (KBr): ν ϭ
From 3-[5-(4-methoxyphenyl)-2-thienyl]acrylic acid (260 mg, 1
mmol) according to general procedure 3. Purification: recrystalliza-
3430, 2925, 1667, 1614, 1550, 1509, 1251 cmϪ1
.
1H NMR (DMSO
d6): δ 2.23 (s, 3H), 3.34 (s, 2H), 3.75 (s, 3H), 6.52 (d, J ϭ 16 Hz,
1H), 6.96 (m, 4H), 7.03 (m, 2H), 7.48 (m, 2H), 7.54 (m, 1H), 7.62
(m, 3H), 7.67 (m, 3H), 7.74 (m, 1H), 7.80 (m, 2H), 7.85 (m, 1H),
10.08 (s, 1H), 10.32 (s, 1H). MS (EI): m/z ϭ 243 (21), 326 (100),
586 (1) Mϩ. Anal. calcd for C36H30N2O4S: C, 73.70; H, 5.15; N,
4.77; S, 5.46; found: C, 73.36; H, 5.29; N, 4.96; S, 5.14.
tion from toluene. Yield: 407 mg (69%). Mp 178°C. IR (KBr): ν ϭ
3241, 3028, 1666, 1645, 1605, 1550, 1506, 1253, 1177 cmϪ1 1H
.
NMR (DMSO d6): δ 2.24 (s, 3H), 3.36 (s, 2H), 3.78 (s, 3H), 6.46
(d, J ϭ 16 Hz, 1H), 6.96Ϫ7.04 (m, 6H), 7.39 (m, 2H), 7.48 (m, 2H),
7.54 (m, 1H), 7.60Ϫ7.66 (m, 4H), 7.67 (m, 2H), 7.74 (m, 1H), 7.85
(m, 1H), 10.08 (s, 1H), 10.30 (s, 1H). MS (EI): m/z ϭ 212 (42), 243
(100), 326 (26), 344 (55), 586 (24) Mϩ. Anal. calcd for
C36H30N2O4S: C, 73.70; H, 5.15; N, 4.77; S, 5.46; found: C, 73.57;
H, 5.13; N, 4.98; S, 5.25.
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[4-(4-methyl-
sulfonylphenyl)-2-thienyl]acrylic acid amide (11e)
From 3-[4-(4-methylsulfonylphenyl)-2-thienyl]acrylic acid (308 mg,
1 mmol) according to general procedure 3. Purification: recrystalli-
zation from toluene/dioxan. Yield: 342 mg (60%). Mp 220°C. IR
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-[5-(4-methyl-
sulfonylphenyl)-2-thienyl]acrylic acid amide (12e)
(KBr): ν ϭ 3422, 1673, 1633, 1555, 1510, 1141 cmϪ1
.
1H NMR
From 3-[5-(4-methylsulfonylphenyl)-2-thienyl]acrylic acid (231 mg,
0.75 mmol) according to general procedure 3. Purification: recrys-
tallization from toluene/dioxan. Yield: 273 mg (63%). Mp 266°C.
(DMSO d6): δ 2.26 (s, 3H), 3.24 (s, 3H), 3.36 (s, 2H), 6.60 (d, J ϭ
16 Hz, 1H), 6.99 (m, 2H), 7.02Ϫ7.07 (m, 2H), 7.51 (m, 4H),
7.57Ϫ7.73 (m, 4H), 7.77 (m, 1H), 7.87 (m, 1H), 7.96Ϫ8.01 (m, 4H),
8.20 (m, 1H), 10.09 (s, 1H), 10.36 (s, 1H). MS (EI): m/z ϭ 212
(99), 291 (81), 326 (61), 344 (100), 634 (23) Mϩ. Anal. calcd for
C36H30N2O5S2: C, 68.12; H, 4.76; N, 4.41; S, 10.10; found: C, 68.02;
H, 4.92; N, 4.44; S, 9.83.
IR (KBr): ν ϭ 3396, 2927, 1560, 1507, 1152 cmϪ1 1H NMR
.
(DMSO d6): δ 2.26 (s, 3H), 3.26 (s, 3H), 3.36 (s, 2H), 6.60 (d, J ϭ
16 Hz, 1H), 6.99 (m, 2H), 7.05 (m, 2H), 7.48Ϫ7.52 (m, 4H), 7.58
(m, 2H), 7.63Ϫ7.71 (m, 2H), 7.75 (m, 2H), 7.88 (m, 1H), 7.95 (m,
4H), 10.09 (s, 1H), 10.37 (s, 1H). MS (EI): m/z ϭ 212 (76), 291 (80),
326 (58), 344 (100), 634 (16) Mϩ. Anal. calcd for C36H30N2O5S2:
C, 68.12; H, 4.76; N, 4.41; S, 10.10; found: C, 67.97; H, 4.70; N,
4.57; S, 10.31.
N-[3-Benzoyl-4-(4-tolylacetylamino)phenyl]-3-(5-phenyl-2-
thienyl)acrylic acid amide (12a)
From 3-[5-phenyl-2-thienyl]acrylic acid (230 mg, 1 mmol) according
to general procedure 3. Purification: recrystallization from toluene.
Yield: 258 mg (46%). Mp 172°C. IR (KBr): ν ϭ 3436, 1653, 1560,
N-[3-Benzoyl-4-(2-p-tolylacetylamino)phenyl]-3-biphenyl-3-yl ac-
rylic acid amide (13b)
1543, 1507, 1400 cmϪ1
.
1H NMR (DMSO d6): δ 2.20 (s, 3H), 3.31
From 3-biphenylylacrylic acid (673 mg, 3 mmol) according to gen-
eral procedure 3. Purification: recrystallization from toluene. Yield:
991 mg (60%). Mp 183°C. IR (KBr): ν ϭ 1685, 1659, 1645, 1552,
1503, 1399 cmϪ1. 1H NMR (DMSO d6): δ 2.24 (s, 3H), 3.35 (s, 2H),
6.84 (d, J ϭ 16 Hz, 1H), 6.97Ϫ7.04 (m, 4H), 7.38Ϫ7.70 (m, 15H),
7.60 (m, 1H), 7.87 (m, 2H), 10.07 (s, 1H), 10.30 (s, 1H). MS (EI):
m/z ϭ 207 (25), 344 (25), 418 (21), 550 (100) Mϩ, 551 (42). Anal.
(s, 2H), 6.49 (d, J ϭ 16 Hz, 1H), 6.93 (m, 2H), 7.00 (m, 2H), 7.31
(m, 1H), 7.38Ϫ7.47 (m, 5H), 7.51 (m, 2H), 7.59 (m, 2H), 7.63Ϫ7.66
(m, 4H), 7.72 (m, 1H), 7.82 (m, 1H), 10.06 (s, 1H), 10.32 (s, 1H).
MS (EI): m/z ϭ 213 (100), 344 (38), 557 [MϩH]ϩ. Anal. calcd for
C35H28N2O3S: C, 75.52; H, 5.07; N, 5.03; S, 5.76; found: C, 75.42;
H, 5.07; N, 5.24; S, 5.62.