Molecules 2015, 20
12310
1
32.22, 129.96, 129.38, 128.54, 128.01, 124.37, 122.41, 117.32, 51.71, 45.88, 30.33, 23.64. GC-MS:
8
1
79
m/z found: 442 (M calculated for C21
H
19BrN
2
O S: 442); m/z (%) = 444 (M, 1, Br), 442 (M, 1, Br),
2
8
1
79
81
79
81
79
81
4
01 (5, Br), 399 (5, Br), 359 (6, Br), 357 (6, Br), 345 (2, Br), 343 (2, Br), 310 (1, Br), 308
7
9
(
1, Br), 149 (4), 93 (18), 77 (15), 43 (100), 39 (12), 27 (2).
N-Acetyl-4-(p-tolylamino)-4-(2-phenylthiazol-4-yl)butan-2-one (5e): yellow liquid, yield: 76%,
1H-NMR (600 MHz, CDCl
) δ 7.94–7.79 (m, J = 6.5, 2.7 Hz, 2H), 7.46–7.35 (m, J = 4.9 Hz, 3H), 7.21
s, 1H), 7.16–7.05 (m, 2H), 7.02–6.75 (m, 2H), 6.45 (t, J = 7.5 Hz, 1H), 3.08 (ddd, J = 24.6, 16.6, 7.5
3
(
13
Hz, 2H), 2.33 (s, 3H), 2.14 (s, 3H), 1.79 (s, 3H). C-NMR (151 MHz, CDCl
3
) δ 205.97, 170.81, 167.17,
55.86, 138.35, 137.50, 133.71, 130.04, 129.92, 129.63, 128.96, 126.54, 116.88, 51.47, 45.81, 30.30,
3.55, 21.19. GC-MS: m/z found: 378 (M calculated for C22 S: 378); m/z (%) = 379 (M + 1, 3),
78 (M, 2), 335 (9), 293 (10), 279 (4), 230 (4), 188 (10), 149 (4), 91 (4), 77 (7), 65 (5), 43 (100), 39 (8).
1
2
3
H
22
N
2
O
2
N-Acetyl-4-(p-tolylamino)-4-(2-m-tolylthiazol-4-yl)butan-2-one (5f): yellow liquid, yield: 75%,
1H-NMR (600 MHz, CDCl
) δ 7.65 (s, 1H), 7.38 (d, J = 8.3 Hz, 1H), 7.29 (t, J = 7.6 Hz, 1H), 7.22 (d,
3
J = 7.5 Hz, 1H), 7.18 (s, 1H), 7.11–7.08 (m, J = 8.2 Hz, 2H), 7.01–6.71 (m, J = 46.4 Hz, 2H), 6.46 (t,
J = 7.5 Hz, 1H), 3.09 (ddd, J = 24.6, 16.5, 7.5 Hz, 2H), 2.40 (s, 3H), 2.34 (s, 3H), 2.14 (s, 3H), 1.80 (s,
1
3
3
H). C-NMR (151 MHz, CDCl
29.67, 129.53, 128.90, 127.19, 123.80, 120.11, 116.79, 51.55, 45.86, 30.28, 23.55, 21.49, 21.20. GC-MS:
S: 392); m/z (%) = 393 (M + 1, 1), 392 (M, 2), 349 (14),
07 (14), 293 (6), 243 (5), 228 (13), 202 (3), 149 (21), 107 (28), 91 (9), 77 (3), 65 (9), 43 (100), 39 (22).
3
) δ 206.07, 170.90, 167.51, 155.67, 138.75, 133.88, 130.91, 129.93,
1
m/z found: 392 (M calculated for C23
H
24
N
2
O
2
3
N-Acetyl-4-(p-tolylamino)-4-(2-p-tolylthiazol-4-yl)butan-2-one (5g): yellow liquid, yield: 76%,
1H-NMR (600 MHz, CDCl
) δ 7.73 (d, J = 8.0 Hz, 2H), 7.19 (d, J = 7.7 Hz, 2H), 7.14 (s, 1H), 7.12–6.74
m, 4H), 6.45 (t, J = 7.5 Hz, 1H), 3.06 (ddd, J = 24.6, 16.5, 7.5 Hz, 2H), 2.36 (s, 3H), 2.32 (s, 3H), 2.13
3
(
(
1
3
s, 3H), 1.78 (s, 3H). C-NMR (151 MHz, CDCl
37.46, 131.08, 129.84, 129.61, 129.58, 126.42, 116.29, 51.44, 45.77, 30.23, 23.49, 21.45, 21.13.
GC-MS: m/z found: 392 (M calculated for C23 S: 392); m/z (%) = 393 (M + 1, 1), 392 (M, 4),
49 (24), 307 (29), 293 (7), 243 (27), 228 (44), 202 (30), 149 (36), 135 (7), 118 (8), 107 (62), 91 (21),
7 (19), 65 (14), 43 (100), 39 (27).
3
) δ 205.96, 170.71, 167.29, 155.63, 140.21, 138.26,
1
H
24
N
2
O
2
3
7
N-Acetyl-4-(p-tolylamino)-4-(2-(4-bromophenyl)thiazol-4-yl)butan-2-one (5h): semisolid, yield: 80%,
1H-NMR (600 MHz, CDCl
) δ 7.67 (d, J = 8.4 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 7.21 (s, 1H), 7.11–6.73
m, J = 139.3 Hz, 4H), 6.41 (t, J = 7.4 Hz, 1H), 3.05 (ddd, J = 24.6, 16.7, 7.5 Hz, 2H), 2.30 (s, 3H), 2.10
3
(
(
1
3
s, 3H), 1.77 (s, 3H). C-NMR (151 MHz, CDCl
3
) δ 205.74, 170.90, 165.74, 155.98, 138.34, 137.28,
1
32.53, 132.00, 129.85, 129.45, 127.83, 124.10, 117.17, 51.35, 45.64, 30.17, 23.36, 21.08. GC-MS: m/z
8
1
81
found: 456 (M calculated for C22
H
21BrN
2
O S: 456); m/z (%) = 459 (M + 1, 5, Br), 458 (M, 6, Br),
2
7
9
79
81
79
81
79
4
57 (M + 1, 5, Br), 456 (M, 5, Br), 415 (25, Br), 413 (26, Br), 373 (26, Br), 371 (25, Br), 359
8
1
79
81
79
81
79
(
9, Br), 357 (11, Br), 310 (6, Br), 308 (6, Br), 268 (13, Br), 266 (17, Br), 191 (10), 149 (45),
07 (48), 86 (68), 84 (99), 43 (100), 35 (34).
1
N-Acetyl-4-(furan-2-yl)-4-(phenylamino)butan-2-one (5i): yellow solid, mp: 80 °C, yield: 75%,
1H-NMR (600 MHz, CDCl
) δ 7.32–7.26 (m, 5H), 6.48 (t, J = 7.6 Hz, 1H) overlapped with 6.8–6.3 (m,
3