188
S. Piras et al. / IL FARMACO 59 (2004) 185–194
Table 1
The m.p., yields, analytical and spectroscopic (IR, UV, 1H NMR) data
Compounds m.p. (°C) a
Yields Analysis for
(%)
IR (nujol)
UV (EtOH)
(kmax nm)
1H NMRb, dH (J in Hz)
(mmax cm–1
)
1
2
3
4
114–116 (a)
132–135 (a)
159–161 (a)
86–87 (a)
89
90
98
92
C
C
C
C
17H12F2N2O3
23H18N3O3
21H16N2O3S
20H18N2O5
1730, 1580
325, 225, 204
[A] 3.69 (2H, s, CH2); 3.74 (3H, s, CH3); 7.22 (2H, d, J = 8.0,
H-3′, 5′); 7.38 (2H, d, J = 8.0, H-2′, 6′); 7.60–7.45 (1H, m,
H-5); 7.90–7.75 (1H, m, H-8); 8.67 (1H, s, H-3)
[A] 3.69 (2H, s, CH2); 3.73 (3H, s, CH3); 7.24 (2H, d, J = 8.4,
H-3′, 5′); 7.40 (2H, d, J = 8.4, H-2′, 6′); 7.74–7.50 (6H, m,
arom); 8.23–8.10 (2H, m, H-8 + arom)
1750, 1580
341, 242, 206
360, 266, 212
302, 243, 206
1740, 1670,
1580
[B] 3.71 (2H, s, CH2); 3.74 (3H, s, CH3); 7.23–7.19 (2H, m,
H3″, 4″); 7.32 (2H, d, J = 8.8, H-2′, 6′); 7.68–7.54 (3H, m,
arom); 8.05 (1H, m, H-5″); 8.30 (1H, m, H-8)
1750, 1580
[A] 1.48 (3H, t, CH2CH3); 3.69 (2H, s, CH2); 3.74 (3H, s,
COOCH3); 4.57 (2H, q, CH2CH3); 7.26 (2H, d, J = 8.6, H-3′,
5′); 7.40 (2H, d, J = 8.6, H-2′, 6′); 7.80–7.62 (3H, m, arom);
8.20–8.10 (1H, dd, J = 7.6 and 1.2, H-8)
5
6
139–141 (a)
78–80 (a)
89
60
C
C
21H17F3N2O5
1730, 1580
332, 243, 206
332, 228, 207
[A] 1.50 (3H, t, CH2CH3); 3.70 (2H, s, CH2); 3.74 (3H, s,
COOCH3); 4.58 (2H, q, CH2CH3); 7.24 (2H, d, J = 8.6, H-3′,
5′); 7.40 (2H, d, J = 8.6, H-2′, 6′); 7.86–7.80 (1H, dd,
J = 8.6 and 1.8, H-6); 8.08 (1H, s, H-8); 8.25 (1H, d, J = 8.8,
H-5)
20H16F2N2O5
1730
[A] 1.48 (3H, t, CH2CH3); 3.69 (2H, s, CH2); 3.74 (3H, s,
CH3); 4.56 (2H, q, CH2CH3); 7.23 (2H, d, J = 8.6, H-3′, 5′);
7.38 (2H, d, J = 8.6, H-2′, 6′); 7.60–7.45 (1H, m, H-5);
7.95–785 (1H, m, H-8)
7
246–248
215–217
163–165
120–121
161–163
139–142 (a)
69
95
97
89
77
65
C
C
C
C
C
C
22H16N2O3
20H14N2O3S
17H12N2O5
18H11F3N2O5
17H10F2N2O5
31H31N3O6
1700, 1580,
1560
341, 243, 206
361, 266, 212
325, 242, 206
323, 207
[B] 3.66 (2H, s, CH2); 7.24 (2H, d, J = 8.6, H-3′, 5′); 7.40
(2H, d, J = 8.6, H-2′, 6′); 7.82–7.50 (6H, m, arom); 8.24–8.10
(2H, m, arom)
8
1715, 1620
1720, 1570
[B] 3.66 (2H, s, CH2); 7.26–7.21 (2H, m, H-3″, 4″); 7.30 (2H,
d, J = 8.4, H-3′, 5′); 7.41 (2H, d, J = 8.4, H-2′, 6′); 7.70–7.50
(3H, m, arom); 8.00 (1H, m, H-5″); 8.29 (1H, m, H-8)
[B] 3.62 (2H, s, CH2); 7.27 (2H, d, J = 8.4, H-3′, 5′); 7.41
(2H, d, J = 8.4, H-2′, 6′); 7.78–7.75 (3H, m, arom); 8.12–8.10
(1H, m, H-8)
9
10
11
12
3450, 1730,
1570
[B] 3.66 (2H, s, CH2); 7.25 (2H, d, J = 8.6, H-3′, 5′); 7.37
(2H, d, J = 8.6, H-2′, 6′); 7.82–7.74 (1H, m, H-6); 8.07 (1H, s,
H-8); 8.25 (1H, d, J = 8.6, H-5)
3500, 1730,
1570
327, 206
[A] 3.66 (2H, s, CH2); 7.21 (2H, d, J = 8.2, H-3′, 5′); 7.40
(2H, d, J = 8.2, H-2′, 6′); 7.60–7.45 (1H, m, H-5); 8.00–7.80
(1H, m, H-8)
3300, 1730,
1650, 1540
341, 243, 206
[A] 1.35–1.20 (6H, m, 2CH2CH3); 2.45–1.82 (4H, m,
CH2CH2); 3.67 (2H, s, CH2Ph); 4.22 –4.09 (4H, m,
2CH2CH3); 4.62–4.75 (1H, m, CH); 6.28 (1H, d, J = 7.4,
NH); 7.29 (2H, d, J = 8.4, H-2′, 6′); 7.80–7.55 (6H, m, arom);
8.25–8.10 (2H, m, arom)
13
14
177–180 (a)
105–108 (a)
39
14
C
C
29H29N3O6S
3300, 1750,
1650, 1560
361, 266, 211
331, 243, 205
[A] 1.32–1.21 (6H, m, 2CH2CH3); 2.40–1.90 (4H, m,
CH2CH2); 3.68 (2H, s, CH2Ph); 4.30–4.10 (4H, m,
2CH2CH3); 4.59–4.72 (1H, m, CH); 6.31 (1H, d, J = 7.4,
NH); 7.25–7.21 (2H, m, H-3″, 4″); 7.35 (2H, d, J = 8.6, H-3′,
5′); 7.39 (2H, d, J = 8.6, H-2′, 6′); 7.70–7.75 (3H, m, arom);
8.05 (1H, m, H-5″); 8.32 (1H, d, J = 8.2, arom)
[A] 1.42–1.20 (12H, m, 4CH2CH3); 2.65–1.80 (8H, m,
2CH2CH2); 3.66 (2H, s, CH2Ph); 4.20–4.10 (4H, m,
2CH2CH3); 4.30–4.20 (4H, m, 2CH2CH3); 4.67–4.50 (1H, m,
CH); 4.95–4.85 (1H, m, CH); 6.38 (1H, d, J = 7.2, NH); 7.28
(2H, d, J = 7.0, H-3′, 5′); 7.32 (2H, d, J = 7.0, H-2′, 6′);
7.85–7.70 (3H, m, arom); 8.13 (1H, dd, J = 8.6 and 1.4, H-8);
8.39 (1H, d, J = 7.8, NH)
35H42N4O11
3300, 1730,
1670
(continued on next page)