RSC Advances
Paper
The X-ray crystal-structure determinations of complexes 1, 3, 4, 156.03, 140.27, 129.69, 129.28, 125.49, 122.64, 121.59, 121.33,
and 7 were obtained on a Bruker APEX DUO CCD system. 120.24, 118.62, 115.27, 114.62, 108.57, 68.09, 68.00, 42.89,
5
+
2
9.22, 29.08, 28.84, 27.11, 25.81. EI-MS: m/z ¼ 414.41[M] . Anal.
calcd for C H N O : C, 78.23; H, 7.29; N, 6.76. Found: C, 78.29;
2
7
30 2 2
Synthetic procedures for 1b–7b
H, 7.34; N, 6.70.
A mixture of compounds 1a, 2a, 3a, 4a, 5a, 6a or 7a (1 mmol), N-
(
4-hydroxyphenyl)formamide (1.5 mmol), K CO (6 mmol) were
2 3
Synthetic procedures for 1c–7c
stirred in DMF (50 ml) for overnight under an argon atmosphere
at 60 C. Aer completion of present reaction, DMF was A CH
removed from reaction system by vacuum distillation. The mmol) and triethylamine (5 ml) was cooled to 0 C. To the
ꢂ
2
Cl
2
suspension (15 ml) of 1b, 2b, 3b, 4b, 5b, 6b or 7b (0.6
ꢂ
residual mixture was extracted with dichloromethane (3 ꢀ 20 mixture was added dropwise a CH
ml). The combined organic layers were washed with brine, dried phosgene (0.66 mmol). The mixture was reuxed for 3 h, then
Na SO ), and concentrated in vacuo. The residues were puried 10% aq. Na CO (50 ml) was added dropwise at room temper-
2 2
Cl solution (10 ml) of tri-
(
2
4
2
3
by column chromatography, affording the expected white solid ature. The mixture was extracted with dichloromethane (3 ꢀ 20
products 1b–7b in a yield of 71%, 69%, 68%, 75%, 73%, 70%, ml). The combined organic layers were washed with brine, dried
6
5%, respectively. The NMR data of 1b and 2b were not ob- (Na
2
SO
4
), and concentrated in vacuo. The residues were puried
1
tained due to the poor solubility. 3b: H NMR (400 MHz, CDCl
3
): by column chromatography, affording the expected yellow solid
d (ppm) ¼ 8.49–8.30 (m, 1H), 8.11 (d, J ¼ 8 Hz, 2H), 7.49–7.39 products 1c–7c in a yield of 81%, 79%, 82%, 77%, 83%, 78%,
1
(
2
m, 5H), 7.23 (d, J ¼ 8 Hz, 2H), 7.08–6.97 (m, 2H), 6.83–6.80 (m, 74%, respectively. 1c: H NMR (400 MHz, CDCl
3
): d (ppm) ¼ 8.09
H), 4.41 (t, J ¼ 4 Hz, 2H), 3.92 (t, J ¼ 6 Hz, 2H), 2.08 (s, 2H), 1.84 (d, J ¼ 8 Hz, 2H), 7.48 (d, J ¼ 4 Hz, 4H), 7.28–7.19 (m, 4H), 6.73
1
3
1
3
(s, 2H). C NMR (100 MHz, CDCl
3
): d (ppm) ¼ 162.99, 158.83, (d, J ¼ 8 Hz, 2H), 4.72 (t, J ¼ 6 Hz, 2H), 4.34 (t, J ¼ 6 Hz, 2H).
C
1
1
4
56.77, 155.89, 140.26, 129.84, 129.43, 125.62, 122.77, 121.67, NMR (100 MHz, CDCl ): d (ppm) ¼ 162.78, 158.38, 140.36,
3
21.51, 120.35, 118.79, 115.34, 114.70, 108.58, 67.75, 67.65, 127.58, 125.74, 122.98, 120.36, 119.29, 114.86, 108.59, 66.30,
+
+
2.62, 26.90, 25.78. EI-MS: m/z ¼ 358.42[M] . Anal. calcd for 42.23. EI-MS: m/z ¼ 312.26[M] . Anal. calcd for C21
: C, 77.07; H, 6.19; N, 7.82. Found: C, 77.13; H, 6.12; 80.75; H, 5.16; N, 8.97. Found: C, 80.71; H, 5.22; N, 8.93. 2c: H
16 2
H N O: C,
1
23 22 2 2
C H N O
N, 7.87. 4b: H NMR (400 MHz, CDCl
1
3
): d (ppm) ¼ 8.49–8.31 (m, NMR (400 MHz, CDCl
3
): d (ppm) ¼ 8.09 (d, J ¼ 8 Hz, 2H), 7.39 (d,
1
2
3
1
1
1
4
H), 8.11 (d, J ¼ 8 Hz, 2H), 7.48–7.39 (m, 5H), 7.23 (t, J ¼ 8 Hz, J ¼ 4 Hz, 4H), 7.29–7.20 (m, 4H), 6.80 (d, J ¼ 8 Hz, 2H), 4.56 (t, J
1
3
H), 7.03–6.97 (m, 2H), 6.83–6.80 (m, 2H), 4.36–4.32 (m, 2H), ¼ 6 Hz, 2H), 3.87 (t, J ¼ 6 Hz, 2H), 2.39–2.33 (m, 2H). C NMR
.89 (t, J ¼ 6 Hz, 2H), 1.99–1.92 (m, 2H), 1.82–1.76 (m, 2H), 1.58– (100 MHz, CDCl
3
): d (ppm) ¼ 162.58, 158.63, 140.16, 127.57,
1
3
.51 (m, 2H). C NMR (100 MHz, CDCl ): d (ppm) ¼ 162.67, 125.63, 122.69, 120.23, 118.92, 114.81, 108.34, 64.57, 38.90,
3
+
58.59, 157.10, 156.18, 140.41, 129.79, 129.30, 125.62, 122.87, 28.31. EI-MS: m/z ¼ 326.33[M] . Anal. calcd for C H N O: C,
2
2
18 2
1
21.81, 121.72, 120.37, 118.81, 115.54, 114.91, 108.59, 68.02, 80.96; H, 5.56; N, 8.58. Found: C, 80.91; H, 5.50; N, 8.64. 3c: H
+
2.94, 29.06, 28.79, 23.89. EI-MS: m/z ¼ 372.50[M] . Anal. calcd NMR (400 MHz, CDCl
3
): d (ppm) ¼ 8.11 (d, J ¼ 8 Hz, 2H), 7.48–
24 2 2
for C24H N O
6
8
¼
: C, 77.39; H, 6.49; N, 7.52. Found: C, 77.45; H, 7.39 (m, 4H), 7.27–7.22 (m, 4H), 6.79–6.75 (m, 2H), 4.40 (t, J ¼ 6
1
.56; N, 7.44. 5b: H NMR (400 MHz, CDCl
.30 (m, 1H), 8.10 (d, J ¼ 8 Hz, 2H), 7.58–7.39 (m, 5H), 7.22 (d, J 2H). C NMR (100 MHz, CDCl
8 Hz, 2H), 7.07–6.97 (m, 2H), 6.83–6.80 (m, 2H), 4.32 (t, J ¼ 6 140.33, 127.69, 125.66, 122.90, 120.40, 119.49, 118.91, 114.97,
3
): d (ppm) ¼ 8.49– Hz, 2H), 3.91 (t, J ¼ 6 Hz, 2H), 2.12–2.04 (m, 2H), 1.87–1.80 (m,
13
3
): d (ppm) ¼ 162.74, 159.10,
+
Hz, 2H), 3.88 (t, J ¼ 6 Hz, 2H), 1.91 (s, 2H), 1.72 (s, 2H), 1.47 (s, 108.53, 67.83, 42.61, 26.83, 25.70. EI-MS: m/z ¼ 340.32[M] .
1
3
4
1
1
2
H). C NMR (100 MHz, CDCl ): d (ppm) ¼ 163.03, 158.82, Anal. calcd for C H N O: C, 81.15; H, 5.92; N, 8.23. Found: C,
3
23 20 2
1
56.92, 156.02, 140.30, 129.71, 129.29, 125.54, 122.70, 121.62, 81.07; H, 5.99; N, 8.27. 4c: H NMR (400 MHz, CDCl
3
): d (ppm) ¼
21.46, 120.28, 118.69, 115.32, 114.67, 108.57, 67.87, 42.82, 8.11 (d, J ¼ 8 Hz, 2H), 7.48–7.39 (m, 4H), 7.28 (s, 2H), 7.23 (d, J ¼
+
8.95, 28.85, 26.97, 25.81. EI-MS: m/z ¼ 386.37[M] . Anal. calcd 4 Hz, 2H), 6.78 (d, J ¼ 8 Hz, 2H), 4.35 (t, J ¼ 6 Hz, 2H), 3.89 (t, J ¼
for C25
6
8
H
26
N
2
O
2
: C, 77.69; H, 6.78; N, 7.25. Found: C, 77.65; H, 6 Hz, 2H), 2.00–1.93 (m, 2H), 1.84–1.77 (m, 2H), 1.52 (d, J ¼ 4
1
1
3
.76; N, 7.28. 6b: H NMR (400 MHz, CDCl
3
): d (ppm) ¼ 8.49– Hz, 2H). C NMR (100 MHz, CDCl ): d (ppm) ¼ 162.42, 159.20,
3
.27 (m, 1H), 8.10 (d, J ¼ 8 Hz, 2H), 7.78–7.37 (m, 6H), 7.24–7.13 140.32, 127.65, 125.59, 122.80, 120.35, 118.79, 114.94, 108.53,
+
(
m, 2H), 6.98 (d, J ¼ 8 Hz, 1H), 6.85–6.80 (m, 2H), 4.32–4.28 (m, 67.91, 42.81, 28.84, 28.71, 23.75. EI-MS: m/z ¼ 354.28[M] . Anal.
2
H), 3.87 (t, J ¼ 6 Hz, 2H), 1.88 (s, 2H), 1.72 (s, 2H), 1.39 (s, 6H). calcd for C H N O: C, 81.33; H, 6.26; N, 7.90. Found: C, 81.39;
2
4
22 2
1
3
1
C NMR (100 MHz, CDCl
3
): d (ppm) ¼ 163.11, 158.90, 156.94, H, 6.33; N, 7.85. 5c: H NMR (400 MHz, CDCl ): d (ppm) ¼ 8.11
3
1
1
2
56.03, 140.29, 129.70, 129.28, 125.52, 122.67, 121.60, 121.40, (d, J ¼ 4 Hz, 2H), 7.45–7.39 (m, 4H), 7.28–7.23 (m, 4H), 6.78 (d, J
20.26, 118.65, 115.29, 114.65, 108.57, 68.03, 67.95, 42.89, ¼ 8 Hz, 2H), 4.33 (t, J ¼ 6 Hz, 2H), 3.89–3.84 (m, 2H), 1.91 (d, J ¼
+
13
9.06, 28.82, 27.14, 25.80. EI-MS: m/z ¼ 400.34[M] . Anal. calcd 8 Hz, 2H), 1.72 (d, J ¼ 8 Hz, 2H), 1.45 (s, 4H). C NMR (100 MHz,
for C26
7
8
H
28
N
2
O
2
: C, 77.97; H, 7.05; N, 6.99. Found: C, 77.89; H, CDCl
3
): d (ppm) ¼ 162.36, 159.11, 140.21, 127.48, 125.46,
1
.09; N, 6.90. 7b: H NMR (400 MHz, CDCl
.25 (m, 1H), 8.11–7.92 (m, 3H), 7.48–7.37 (m, 5H), 7.21 (d, J ¼ 8 28.67, 26.82, 25.68. EI-MS: m/z ¼ 368.35[M] . Anal. calcd for
3
): d (ppm) ¼ 8.49– 122.64, 120.19, 118.63, 114.77, 108.48, 67.88, 42.67, 28.74,
+
Hz, 2H), 6.98 (d, J ¼ 8 Hz, 1H), 6.84–6.80 (m, 2H), 4.30–4.26 (m, C H N O: C, 81.49; H, 6.57; N, 7.60. Found: C, 81.46; H, 6.55;
2
5
24 2
1
2
H), 3.88 (t, J ¼ 6 Hz, 2H), 1.87–1.82 (m, 2H), 1.37–1.32 (m, 10H). N, 7.64. 6c: H NMR (400 MHz, CDCl
3
): d (ppm) ¼ 8.11 (d, J ¼ 8
1
3
C NMR (100 MHz, CDCl
3
): d (ppm) ¼ 163.16, 158.95, 156.93, Hz, 2H), 7.48–7.39 (m, 4H), 7.28–7.21 (m, 4H), 6.81 (d, J ¼ 8 Hz,
93762 | RSC Adv., 2015, 5, 93757–93764
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