Molecular diversity in cyclization of Ugi-products…
(
MW = 404.50), found: C, 74.65; H, 7.23; N, 7.18 %]; FT-IR (KBr):
-
1 1
mmax = 3032, 2933, 2856, 1665, 1493 cm ; H NMR (400 MHz, CDCl ):
3
d = 1.12–1.92 (m, 10H), 2.41 (s, 3H), 3.65–3.77 (m, 2H), 3.83–3.86 (m, 1H),
4
.14 (d, J = 16.6 Hz, 1H), 4.54 (t, J = 3.8 Hz, 1H), 4.89 (d, J = 16.6 Hz,
H), 7.26 (s, 1H), 7.29 (d, J = 7.8, 4H), 7.40 (t, J = 7.8, 2H), 7.83 (d,
1
1
3
J = 8.1 Hz, 2H) ppm; C NMR (100 MHz, CDCl ): d = 21.8, 25.6, 26.2,
3
2
9.4, 30.8, 41.3, 53.9, 55.3, 57.3, 125.6, 127.6, 128.3, 129.5, 129.7, 133.9,
40.3, 144.6, 164.6, 166.9, 195.9 ppm.
1
1
9. 3-(4-Chlorophenyl)-1-cyclohexyl-6-(2-oxo-2-(p-tolyl)ethyl)-4-(p-tolyl)piper-
azine-2,5-dione (3g); M.p.: 232–235 °C; [requires: C, 72.65; H, 6.29; N, 5.29;
C H ClN O (MW = 529.07), found: C, 72.75; H, 6.48; N, 5.45 %]; FT-
3
2
33
2
3
-
1
IR (KBr): m
= 3033, 2927, 2860, 1677, 1605, 1513, 1485, 1430 cm ;
max
1
HNMR (400 MHz, CDCl ): d = 1.07–1.80 (m, 10H), 2.24 (s, 3H), 2.43 (s,
3
3
H), 3.47–3.53 (m, 1H), 3.78–3.90 (m, 2H), 4.60 (t, J = 3.7 Hz, 1H), 5.72 (s,
H), 6.95 (d, J = 8.2 Hz, 2H), 7.03 (d, J = 8.2 Hz, 2H), 7.18 (d, J = 8.5 Hz,
H), 7.23 (d, J = 8.5 Hz, 2H), 7.28 (d, J = 8.0 Hz, 2H), 7.85 (d, J = 8.0,
1
2
2
4
1
1
3
H) ppm; C NMR (100 MHz, CDCl ): d = 21.2, 21.9, 25.5, 26.3, 30.2,
3
0.9, 56.2, 59.1, 67.3, 127.2, 128.2, 128.9, 129.65, 129.90, 129.92, 134.0,
36.9, 137.6, 144.8, 166.1, 167.5, 196.4 ppm.
2
0. 1-Cyclohexyl-3-(4-(dimethylamino)phenyl)-6-(2-oxo-2-(p-tolyl) ethyl)-4-(p-
tolyl) piperazine-2,5-dione (3h); M.p.: 153–159 °C; [requires: C, 75.95; H,
7
8
.31; N, 7.81; C H N O (MW = 537.69), found: C, 76.22; H, 7.51; N,
34 39 3 3
-
1 1
.02 %]; FT-IR (KBr): mmax = 3029, 2926, 2860, 2799, 1675, 1477 cm ; H
NMR (400 MHz, CDCl ): d = 1.06–2.20 (m, 10H), 2.23 (s, 3H), 2.42 (s, 3H),
3
2
.91 (s, 6H), 3.42–3.52 (m, 1H), 3.82–3.87 (m, 2H), 4.63 (t, J = 3.7 Hz, 1H),
.54 (s, 1H), 6.96 (d, J = 8.2 Hz, 2H), 7.02 (d, J = 8.1 Hz, 2H), 7.11 (d,
5
J = 8.2 Hz, 2H), 7.26–7.29 (m, 4H), 7.86 (d, J = 8.1 Hz, 2H) ppm; CNMR
1
3
(
100 MHz, CDCl ): d = 21.2, 21.8, 25.6, 26.4, 30.1, 40.9, 56.2, 59.1, 67.5,
3
127.3, 128.2, 129.1, 129.6, 129.8, 134.2, 137.2, 144.6, 167.3, 196.3 ppm.
1. 3-(4-Chlorophenyl)-1-cyclohexyl-6-(2-(4-methoxyphenyl)-2-oxoethyl)-4-(p-
2
tolyl) piperazine-2,5-dione (3i); M.p.: 241–245 °C; [requires: C, 70.51; H,
6
.10; N, 5.14; C H ClN O (MW = 545.07), found: C, 70.21; H, 6.33; N,
32 33 2 4
-
1
5
.24 %]; FT-IR (KBr): mmax = 3010, 2928, 2587, 1675, 1489, 1434 cm ;
1
H NMR (400 MHz, CDCl ): d = 1.08–1.80 (m, 10H), 2.23 (s, 3H),
3
3
.46–3.52 (m, 2H), 3.79–3.82 (m, 1H), 3.88 (s, 3H), 4.59 (t, J = 3.7 Hz, 1H),
.71 (s, 1H), 6.94–6.97 (m, 4H), 7.02 (d, J = 8.5 Hz, 2H), 7.18 (d,
5
J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 7.94 (d, J = 8.5 Hz, 2H) ppm;
1
3
C NMR (100 MHz, CDCl ): d = 21.2, 25.5, 26.2, 26.3, 30.2, 40.6, 55.7,
3
5
1
6.3, 59.1, 67.3, 114.1, 127.2, 128.9, 129.5, 129.9, 130.4, 134.0, 137.0,
37.2, 137.6, 164.1, 166.1, 167.6, 195.2 ppm.
2
2. 1-Cyclohexyl-3-(2-oxo-2-(p-tolyl)ethyl)-4,6-di-p-tolylpiperazine-2,5-dione (3j);
M.p.: 223–226 °C; [requires: C, 77.92; H, 7.13; N, 5.51 C H N O
3
3 36 2 3
(
MW = 508.65), found: C, 78.20; H, 7.41; N, 5.71 %]; FT-IR (KBr):
1
-1
mmax = 3029, 2924, 2860, 1678, 1606, 1513, 1432 cm ; H NMR
(
400 MHz, CDCl ): d = 1.04–2.04 (m, 10H), 2.20 (s, 3H), 2.24 (s, 3H), 2.40
3
(s, 3H), 3.43–3.49 (m, 1H), 3.76–3.86 (m, 2H), 4.59 (t, J = 3.1 Hz, 1H), 5.60 (s,
123