J IRAN CHEM SOC
were obtained in a purified form and no extra purification
was needed.
125.18, 126.28, 128.91, 134.27, 138.12, 139.90, 140.18,
−1
146.02, 148.64; IR (neat) ν (cm ): 690, 754, 1094, 1225,
433, 1596, 1872, 1950, 2856, 3396; MS (EI): m/z calcd
for C H N O : 310.09542; found: 310.
1
Compound (5a)
1
7
14
2
4
Light tan solid; m.p = 233 °C; 1H NMR (400 MHz,
DMSO-d ) δ (ppm): 2.89 (s, 3H, CH ), 6.56 (s, 1H, aro-
Compound (5f)
6
3
matic CH), 6.69 (s, 1H, aromatic CH), 7.40 (m, 2H, two
aromatic CH), 7.52 (m, 2H, two aromatic CH), 7.82 (m,
Brown solid; m.p = 282 °C (decomposed); 1H NMR
(400 MHz, DMSO-d ) δ (ppm): 2.89 (s, 3H, CH ), 7.32
6
3
1
3
1
H, aromatic CH), 8.78 (br, OH); C NMR (100 MHz,
(d, J = 7.2, 1H, aromatic CH), 7.50 (d, J = 7.4, 1H, aro-
DMSO-d ) δ (ppm): 13.61, 99.82, 106.18, 107.05, 119.13,
matic CH), 7.70 (m, 2H, two aromatic CH), 7.80 (t, 1H,
6
1
3
1
1
2
20.32, 126.52, 128.22, 129.21, 129.50, 137.47, 144.39,
46.91, 147.35, 148.57, 151.73; IR (neat) ν (cm ): 3488,
924, 2853, 1945, 1596, 1457, 1125, 725, 689; MS (EI):
aromatic CH), 8.69 (br, OH); C NMR (100 MHz, DMSO-
d6) δ (ppm): 13.90, 107.47, 115.60, 117.77, 119.28, 123.34,
126.38, 140.20, 141.33, 145.01, 146.80, 147.20, 149.69; IR
−
1
−1
m/z calcd for C H N O : 280.08486; found: 280.
(neat) ν (cm ): 689, 754, 1158, 1274, 1457, 1596, 2853,
1
6
12
2
3
2
924, 2952, 3488; MS (EI): m/z calcd for C H N O :
16 12 2 3
Compound (5a); obtained from the reaction of 1g and I
280.08486; found: 280.
Light tan solid; m.p = 233 °C; 1H NMR (400 MHz,
DMSO-d ) δ (ppm): 2.89 (s, 3H, CH ), 6.29 (s, 1H, aro-
Compound (5f); obtained from the reaction of 1h and I
6
3
matic CH), 6.42 (s, 1H, aromatic CH), 7.26 (m, 2H, two
aromatic CH), 7.49 (m, 2H, two aromatic CH), 7.86 (m,
Brown solid; m.p = 282 °C (decomposed); 1H NMR
(400 MHz, DMSO-d ) δ (ppm): 2.89 (s, 3H, CH ), 7.32
6
3
1
3
1
H, aromatic CH), 8.48 (br, OH), 9.16 (br, OH); C NMR
(d, J = 7.2, 1H, aromatic CH), 7.52 (d, J = 7.4, 1H, aro-
(
100 MHz, DMSO-d ) δ (ppm): 13.64, 99.77, 106.17,
matic CH), 7.70 (m, 2H, two aromatic CH), 7.80 (t, 1H,
6
1
3
1
1
07.08, 118.43, 120.79, 126.26, 128.23, 129.02, 129.63,
36.00, 144.68, 146.93, 148.38, 148.80, 151.89; IR (neat)
aromatic CH), 8.70 (br, OH); C NMR (100 MHz, DMSO-
d6) δ (ppm): 13.92, 107.52, 115.59, 117.75, 119.20, 123.40,
126.30, 140.33, 141.34, 144.94, 146.72, 148.15, 149.74;
−1
ν (cm ): 3069, 2921, 2796, 1950, 1597, 1496, 1303,
−1
7
56, 690; MS (EI): m/z calcd for C H N O : 280.08486;
IR (neat) ν (cm ): 688, 755, 1111, 1303, 1457, 1595,
2802, 2922, 2952, 3068, 3406; MS (EI): m/z calcd for
C H N O : 280.08486; found: 280.
1
6
12
2
3
found: 280.
1
6
12
2
3
Compound (5b)
Compound (3d)
1
Light brown solid; m.p = 242 °C (decomposed); H NMR
1
(
400 MHz, DMSO-d ) δ (ppm): 1.96 (s, 3H, CH ), 2.26 (s,
Light gray solid; m.p = 266 °C (decomposed); H NMR
(400 MHz, DMSO-d ) δ (ppm): 1.97 (s, 3H, CH ), 2.09 (s,
6
3
3
H, CH ), 6.19 (s, 1H, aromatic CH), 7.30 (m, 1H, aromatic
3
6
3
CH), 7.50 (m, 1H, aromatic CH), 7.57 (m, 1H, aromatic
CH), 7.87 (d, 1H, aromatic CH), 7.92 (d, 1H, aromatic
CH), 9.12 (s, OH), 9.58 (s, OH); C NMR (100 MHz,
3H, CH ), 6.52 (s, 1H, aromatic CH), 6.66 (s, 1H, aromatic
3
CH), 7.23 (t, 1H, aromatic CH), 7.43 (m, 2H, two aromatic
CH), 7.77 (m, 2H, two aromatic CH), 8.68 (s, OH), 10.61
1
3
1
3
DMSO-d ) δ (ppm): 9.19, 13.65, 104.08, 107.82, 113.77,
(s, OH), 10.99 (s, OH); C NMR (100 MHz, DMSO-d6)
δ (ppm): 13.12, 19.00, 117.07, 118.20, 120.03, 120.79,
124.06, 125.04, 128.02, 128.40, 128.78, 131.02, 139.06,
6
1
1
6
18.59, 119.96, 125.40, 126.42, 129.21, 129.50, 141.90,
42.79, 144.42, 145.06, 147.40, 157.97; IR (neat) ν (cm ):
90, 754, 1133, 1497, 1596, 1872, 1950, 2856, 3396; MS
−1
−1
142.66, 144.36, 146.56, 174.57; IR (neat) ν (cm ): 691,
(
EI): m/z calcd for C H N O : 294.10052; found: 294.
761, 1112, 1442, 1527, 1881, 1950, 2785, 2920, 3070,
1
6
12
2
3
3
511; MS (EI): m/z calcd for C H N O : 296.11618;
17 16 2 3
Compound (5c)
found: 296.
1
Amorphous brown solid; m.p = 210 °C (decomposed); H
Compound (3e)
NMR (400 MHz, DMSO-d ) δ (ppm): 2.13 (s, 3H, CH ),
6
3
1
3
.73 (s, 3H, CH ), 6.44 (s, 1H, aromatic CH), 7.20 (m, 1H,
Light tan solid; m.p = 235 °C (decomposed); H NMR
(400 MHz, DMSO-d ) δ (ppm): 1.26 (s, 9H, 3CH ), 1.91 (s,
3
aromatic CH), 7.44 (t, 2H, two aromatic CH), 7.70 (d, 1H,
aromatic CH), 7.88 (d, 1H, aromatic CH), 8.50 (br, OH),
6
3
3H, CH ), 6.68 (s, 1H, aromatic CH), 6.82 (s, 1H, aromatic
CH), 7.17 (d, 1H, aromatic CH), 7.33 (d, 1H, aromatic
CH), 7.44 (t, 1H, aromatic CH), 7.56 (t, 1H, aromatic CH),
3
1
3
9
.17 (br, OH); C NMR (100 MHz, DMSO-d ) δ (ppm):
6
1
4.05, 56.07, 102.96, 109.15, 118.19, 118.43, 124.56,
1
3