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RSC Advances
DOI: 10.1039/C5RA09407K
17c: Yield 70%;White solid; mp 136ꢀ140 °C; 1H NMR (300
3H), 2.19 (s, 2H); 13C NMR (101 MHz, DMSOꢀd6) δ 192.8,
158.5, 144.9, 134.4, 133.8, 133.4, 130.2, 130.0, 129.5, 128.9,
128.5, 128.1, 125.0, 122.8, 121.4, 115.1, 64.6, 53.1, 45.2, 35.1,
29.0, 9.5
MHz, DMSOꢀd6) δ 8.54 (s, 1H), 7.72 (d, J = 7.2 Hz, 2H), 7.62 (d,
J = 13.6 Hz, 2H), 7.34 (d, J = 7.7 Hz, 2H), 7.24 (d, J = 7.2 Hz,
2H), 6.93 (d, J = 7.8 Hz, 2H), 5.55 (s, 2H), 4.28 (s, 2H), 3.99 (s,
2H), 3.72 (s, 3H), 2.54 (s, 3H), 2.32 (s, 3H), 2.19 (s, 2H); 13C
NMR (75 MHz, DMSOꢀd6) δ 158.4, 147.1, 144.9, 137.6, 130.0,
129.8, 128.7, 128.3, 125.5, 122.8, 121.4, 121.3, 115.1, 64.6, 52.9,
45.2, 35.1, 29.0, 21.2, 9.5
5
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60 17j: Yield 85%; Light yellow solid; mp 180ꢀ184 °C; H NMR
(400 MHz, DMSO) δ 8.78 (s, 1H), 8.01 (d, J = 7.8 Hz, 4H), 7.62
(d, J = 18.5 Hz, 2H), 7.36 (d, J = 4.8 Hz, 2H), 6.94 (d, J = 4.6 Hz,
2H), 5.59 (s, 2H), 4.28 (s, 2H), 3.99 (s, 2H), 3.73 (s, 3H), 2.60 (s,
3H), 2.54 (s, 3H), 2.19 (s, 2H); 13C NMR (101 MHz, DMSO) δ
1
17d: Yield 59%; Colorless solid; mp 100ꢀ104 °C; H NMR (400
10 MHz, CDCl3) δ 8.13 (s, 1H), 7.71 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 65 197.8, 158.5, 146.0, 144.9, 136.3, 135.4, 130.1, 129.4, 128.5,
1.9 Hz, 1H), 7.46 (d, J = 1.8 Hz, 1H), 7.33 (d, J = 8.5 Hz, 2H),
7.23 (d, J = 7.9 Hz, 2H), 6.89 (d, J = 8.6 Hz, 2H), 5.53 (s, 2H),
4.33 (t, J = 6.8 Hz, 2H), 4.00 (t, J = 5.6 Hz, 2H), 3.79 (s, 3H),
2.65 (q, J = 7.6 Hz, 2H), 2.59 (s, 3H), 2.32 – 2.23 (m, 2H), 1.24
15 (t, J = 7.6 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 158.0, 144.0,
143.9, 129.6, 128.1, 127.9, 125.3, 122.6, 121.1, 120.1, 114.6,
63.7, 53.1, 45.2, 34.9, 28.8, 28.3, 15.4, 9.2
125.5, 123.0, 122.8, 121.4, 115.1, 64.6, 53.1, 45.2, 35.1, 29.0,
27.1, 9.5.
17k: Yield 60%; Brown liquid; 1H NMR (300 MHz, DMSOꢀd6) δ
8.60 (s, 1H), 7.88 (s, 2H), 7.62 (d, J = 13.2 Hz, 2H), 7.41 – 7.20
70 (m, 4H), 6.93 (d, J = 6.7 Hz, 2H), 5.56 (s, 2H), 4.28 (s, 2H), 3.99
(s, 2H), 3.72 (s, 3H), 2.54 (s, 3H), 2.18 (s, 2H); 13C NMR (75
MHz, DMSOꢀd6) δ 158.4, 156.9, 146.2, 144.9, 130.0, 128.6,
127.7, 127.5, 122.8, 121.7, 121.4, 116.4, 116.1, 115.8, 115.1,
64.6, 53.0, 45.2, 35.1, 29.0, 9.5
17e: Yield 74%; Light yellow solid; mp 82ꢀ86 °C; 1H NMR (400
MHz, CDCl3) δ 7.77 (s, 1H), 7.71 (d, J = 8.1 Hz, 2H), 7.40 (d, J =
20 8.3 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H), 7.05 (d, J = 2.0 Hz, 1H),
7.02 (d, J = 1.9 Hz, 1H), 6.80 (d, J = 8.5 Hz, 2H), 5.43 (s, 2H),
4.17 (t, J = 7.2 Hz, 2H), 3.88 (t, J = 5.3 Hz, 2H), 3.62 (s, 3H),
2.43 (s, 3H), 2.22 – 2.12 (m, 2H), 1.31 (s, 9H); 13C NMR (101
MHz, CDCl3) δ 158.2, 151.3, 144.0, 129.7, 127.7, 127.6, 127.5,
25 125.7, 125.3, 122.4, 120.8, 114.8, 63.5, 53.5, 45.2, 34.9, 34.6,
31.2, 28.7, 8.9
1
75 17l: Yield 84%; Light yellow solid; mp 124ꢀ126 °C; H NMR
(400 MHz, CDCl3) δ 7.66 (s, 1H), 7.51 – 7.41 (m, 2H), 7.26 (d, J
= 6.6 Hz, 4H), 7.17 (s, 3H), 6.87 (d, J = 6.6 Hz, 2H), 5.46 (s, 2H),
4.36 (t, J = 6.5 Hz, 2H), 4.00 (d, J = 4.7 Hz, 2H), 3.82 (s, 3H),
2.66 (s, 4H), 2.62 (s, 3H), 2.29 (d, J = 4.2 Hz, 2H), 1.98 (s, 2H);
80 13C NMR (101 MHz, CDCl3) δ 158.0, 143.9, 141.6, 129.5, 128.2,
128.1, 127.8, 125.6, 122.6, 121.1, 114.5, 63.6, 53.1, 45.2, 35.0,
35.0, 30.8, 28.8, 25.1, 9.2
1
17f: Yield 45%; Green solid; mp 67ꢀ70 °C; H NMR (400 MHz,
DMSOꢀd6) δ 8.49 (s, 1H), 7.76 (d, J = 7.5 Hz, 2H), 7.62 (d, J =
18.2 Hz, 2H), 7.33 (d, J = 7.3 Hz, 2H), 7.00 (d, J = 7.5 Hz, 2H),
30 6.93 (d, J = 7.3 Hz, 2H), 5.54 (s, 2H), 4.28 (s, 2H), 3.98 (s, 2H),
3.78 (s, 3H), 3.72 (s, 3H), 2.54 (s, 3H), 2.19 (s, 2H); 13C NMR
(101 MHz, DMSOꢀd6) δ 159.4, 158.4, 147.0, 144.9, 130.0, 128.8,
126.9, 123.7, 122.8, 121.4, 120.8, 115.1, 114.7, 64.6, 55.6, 52.9,
45.2, 35.1, 29.0, 9.5
1
17m: Yield 55%;Yellow liquid; H NMR (400 MHz, DMSOꢀd6)
δ 7.88 (s, 1H), 7.64 (d, J = 2.0 Hz, 1H), 7.60 (d, J = 2.0 Hz, 1H),
85 7.26 (d, J = 8.4 Hz, 2H), 6.90 (d, J = 8.5 Hz, 2H), 5.45 (s, 2H),
4.28 (t, J = 6.8 Hz, 2H), 3.97 (t, J = 5.9 Hz, 2H), 3.72 (s, 3H),
2.56 (d, J = 3.8 Hz, 2H), 2.54 (s, 3H), 2.23 – 2.13 (m, 2H), 1.58
(dd, J = 14.4, 7.2 Hz, 2H), 0.89 (t, J = 7.3 Hz, 3H); 13C NMR
(101 MHz, DMSOꢀd6) δ 158.3, 144.9, 129.9, 129.0, 122.8, 121.4,
35 17g: Yield 94%; Yellow solid; mp 80ꢀ84 °C; 1H NMR (300 MHz, 90 115.0, 64.6, 52.6, 45.2, 35.1, 29.0, 27.5, 22.6, 14.0, 9.5
DMSOꢀd6) δ 8.51 (s, 1H), 7.60 (d, J = 13.6 Hz, 2H), 7.39 (s, 1H),
17n: Yield 82%; Light yellow solid; mp 84ꢀ86 °C; 1H NMR (400
7.31 (d, J = 7.2 Hz, 3H), 6.99 (d, J = 8.0 Hz, 1H), 6.91 (d, J = 6.8
MHz, CDCl3) δ 8.40 (s, 1H), 8.07 (s, 1H), 7.89 (d, J = 3.1 Hz,
Hz, 2H), 5.53 (s, 2H), 4.26 (s, 2H), 3.97 (s, 2H), 3.79 (s, 3H),
2H), 7.72 (s, 1H), 7.52 (d, J = 2.6 Hz, 3H), 7.37 (d, J = 2.7 Hz,
3.76 (s, 3H), 3.71 (s, 3H), 2.52 (s, 3H), 2.17 (s, 2H); 13C NMR
4H), 6.90 (d, J = 3.5 Hz, 2H), 5.62 (s, 2H), 4.33 (d, J = 3.3 Hz,
40 (75 MHz, DMSOꢀd6) δ 158.4, 149.4, 149.0, 144.9, 130.0, 128.8,
95 2H), 3.99 (d, J = 2.9 Hz, 2H), 3.79 (s, 3H), 2.59 (s, 3H), 2.28 (d, J
123.8, 123.4, 122.8, 121.4, 121.0, 117.9, 115.1, 112.4, 109.2,
= 1.8 Hz, 2H); 13C NMR (101 MHz, CDCl3) δ 148.8, 140.2,
64.6, 55.9, 52.9, 45.2, 35.1, 29.0, 9.5
139.7, 138.5, 135.6, 134.6, 133.6, 133.1, 132.4, 131.8, 131.4,
130.8, 130.1, 127.6, 126.0, 119.5, 68.3, 58.3, 50.2, 39.9, 33.7,
14.1
17h: Yield 68%; Brown liquid; 1H NMR (400 MHz, DMSOꢀd6) δ
8.48 (s, 1H), 7.75 (d, J = 7.9 Hz, 2H), 7.61 (d, J = 18.2 Hz, 2H),
45 7.45 (d, J = 6.7 Hz, 2H), 7.39 (t, J = 6.8 Hz, 2H), 7.32 (d, J = 7.5
Hz, 3H), 7.07 (d, J = 7.8 Hz, 2H), 6.91 (d, J = 7.9 Hz, 2H), 5.53
(s, 2H), 5.12 (s, 2H), 4.26 (t, J = 6.1 Hz, 2H), 3.97 (s, 2H), 3.71
(s, 3H), 2.53 (s, 3H), 2.23 – 2.13 (m, 2H); 13C NMR (101 MHz,
DMSOꢀd6) δ 158.5, 158.4, 144.9, 137.4, 130.0, 128.9, 128.8,
50 128.3, 128.1, 126.9, 123.9, 122.8, 121.4, 120.9, 118.5, 115.6,
115.1, 69.7, 64.6, 52.9, 45.2, 35.1, 29.0, 9.5
1
100 17o: Yield 88%; Brown solid; mp 150ꢀ153 °C; H NMR (400
MHz, DMSOꢀd6) δ 9.09 (s, 1H), 8.67 (s, 1H), 8.45 (s, 1H), 7.90
(d, J = 4.3 Hz, 2H), 7.75 (d, J = 3.9 Hz, 2H), 7.62 (d, J = 16.9 Hz,
2H), 7.36 (s, 2H), 7.25 (s, 2H), 6.95 (s, 2H), 5.60 (s, 2H), 4.27 (s,
2H), 3.99 (s, 2H), 3.72 (s, 3H), 3.36 (s, 3H), 2.32 (s, 3H), 2.18 (s,
105 2H); 13C NMR (101 MHz, DMSOꢀd6) δ 158.4, 144.8, 144.2,
144.1, 137.7, 130.1, 129.7, 128.5, 125.8, 123.7, 123.5, 122.8,
121.8, 121.3, 116.8, 115.1, 64.6, 53.1, 45.2, 35.1, 29.0, 21.3, 9.5
1
17i: Yield 88%; Brown liquid; H NMR (400 MHz, DMSOꢀd6) δ
10.33 (s, 1H), 8.73 (s, 1H), 7.89 (d, J = 4.2 Hz, 1H), 7.76 (s, 2H),
7.70 – 7.52 (m, 3H), 7.38 (d, J = 5.9 Hz, 2H), 6.94 (d, J = 5.5 Hz,
55 2H), 5.62 (s, 2H), 4.28 (s, 2H), 3.99 (s, 2H), 3.72 (s, 3H), 2.54 (s,
Conclusion
In summary, we have described the synthesis of ionic liquidꢀ
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