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2203, 2141, 1600, 1504, 1253, 829. HRMS (EI) calcd for C15H10OS
[M]+ 238.0452; found 238.0464.
2.22. Colourless solid (0.041 g, 50%); mp 118–120 C. Rf ¼
0.52 (hexane). 1H NMR (500 MHz, CDCl3): d ¼ 7.37 (d, 2H, J ¼ 8
2.16. Colourless solid (0.076 g, 90% (Table 2), 0.065 g, 77% Hz, Ar–H), 7.11 (d, 2H, J ¼ 8 Hz, Ar–H), 6.31–6.29 (m, 1H, –CH),
(Table 3)); mp 128–130 ꢀC. Rf ¼ 0.47 (hexane). 1H NMR (400 2.35 (s, 3H, –CH3), 2.16–2.13 (m, 4H, –CH), 1.66–1.58 (m, 4H,
MHz, CDCl3): d ¼ 7.53–7.48 (m, 2H, Ar–H), 7.35–7.31 (m, 2H, Ar– –CH) ppm. 13C NMR (100 MHz, CDCl3): d ¼ 139.2, 138.6, 132.3,
H), 7.06–6.99 (m, 3H, Ar–H) ppm. 13C NMR (100 MHz, CDCl3): d 129.1, 119.8, 119.0, 83.4, 80.8, 73.5, 71.4, 28.6, 25.9, 22.1, 21.6,
¼ 163.1 (d, JC–F ¼ 252.92 Hz), 134.5 (d, JC–F ¼ 8.62 Hz), 134.4, 21.3 ppm. IR (KBr, cmꢁ1): 2935, 2858, 2132, 1910, 1618, 1506,
134.3, 128.9, 128.8, 127.2, 121.9, 117.8, 115.9 (d, JC–F ¼ 22.03 1431, 1044, 815. HRMS (EI) calcd for C17H16 [M]+ 220.1252;
Hz), 82.5, 80.4, 74.5, 73.5 ppm. IR (lm, cmꢁ1): 3073, 2143, 1888, found 220.1244.
1595, 1502, 1227, 828. HRMS (EI) calcd for C14H7FS [M]+
2.23.13 Colourless solid (0.047 g, 53%); mp 56–58 ꢀC. Rf ¼
1
226.0252; found 226.0250.
0.32 (hexane). H NMR (400 MHz, CDCl3): d ¼ 7.42 (d, 2H, J ¼
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2.17. Colourless solid (0.033 g, 41%); mp 130–132 C. Rf ¼ 8.68 Hz, Ar–H), 6.83 (d, 2H, J ¼ 8.68 Hz, Ar–H), 6.30–6.28 (m, 1H,
0.11 (EtOAc/hexane, 1 : 19). 1H NMR (400 MHz, CDCl3): d ¼ –CH), 3.81 (s, 3H, –OCH3), 2.17–2.10 (m, 4H, –CH), 1.66–1.58
8.60–8.58 (m, 1H, Ar–H), 7.65 (td, 1H, J ¼ 7.78 Hz, 1.81 Hz, Ar– (m, 4H, –CH) ppm. 13C NMR (125 MHz, CDCl3): d ¼ 160.1, 138.4,
H), 7.50–7.48 (m, 1H, Ar–H), 7.42 (d, 2H, J ¼ 8.24 Hz, Ar–H), 133.9, 119.9, 114.1, 83.2, 80.7, 72.9, 71.5, 55.3, 28.7, 25.9, 22.1,
7.26–7.23 (m, 1H, Ar–H), 7.14 (d, 2H, J ¼ 7.80 Hz, Ar–H), 2.35 (s, 21.3 ppm. IR (KBr, cmꢁ1): 2929, 2837, 2130, 1602, 1508, 1291,
3H, –CH3) ppm. 13C NMR (100 MHz, CDCl3): d ¼ 150.3, 142.4, 1251, 1032, 833, 799. HRMS (EI) calcd for C17H16O [M]+
140.0, 136.1, 132.6, 129.2, 128.0, 123.3, 118.1, 82.8, 79.9, 73.9, 236.1201; found 236.1212.
72.9, 21.6 ppm. IR (lm, cmꢁ1): 3046, 2917, 2219, 1577, 1462,
2.24.2h Colourless liquid (0.045 g, 48%); Rf ¼ 0.61 (hexane).
811. HRMS (EI) calcd for C16H11N [M]+ 217.0891; found 1H NMR (400 MHz, CDCl3): d ¼ 7.49–7.46 (m, 2H, Ar–H), 7.33–
217.0894.
7.27 (m, 3H, Ar–H), 5.13–5.08 (m, 1H, –CH), 2.36 (dd, 1H, J ¼
2.18. Colourless solid (0.035 g, 42% (Table 2), 0.027 g, 33% 17.16 Hz, 5.72 Hz, –CH), 2.26 (dd, 1H, J ¼ 16.96 Hz, 6.88 Hz,
1
(Table 3)); mp 128–130 ꢀC. Rf ¼ 0.10 (EtOAc/hexane, 1 : 19). H –CH), 2.04–1.97 (m, 2H, –CH), 1.77–1.72 (m, 1H, –CH), 1.69 (d,
NMR (400 MHz, CDCl3): d ¼ 8.60–8.59 (m, 1H, Ar–H), 7.66 (td, 3H, J ¼ 0.92 Hz, –CH3), 1.62 (s, 3H, –CH3), 1.52–1.43 (m, 1H,
1H, J ¼ 7.68 Hz, 1.68 Hz, Ar–H), 7.53–7.50 (m, 3H, Ar–H), 7.28– –CH), 1.32–1.23 (m, 1H, –CH), 1.03 (d, 3H, J ¼ 6.4 Hz, –CH3)
7.25 (m, 1H, Ar–H), 7.03 (t, 2H, J ¼ 8.46 Hz, Ar–H) ppm. 13C NMR ppm. 13C NMR (100 MHz, CDCl3): d ¼ 132.5, 131.6, 128.7, 128.3,
(100 MHz, CDCl3): d ¼ 163.2 (d, JC–F ¼ 252.92 Hz), 150.3, 142.2, 124.2, 122.1, 83.7, 74.5, 74.4, 65.9, 36.1, 32.1, 26.9, 25.7, 25.5,
136.1, 134.7 (d, JC–F ¼ 8.63 Hz), 128.1, 123.5, 117.4, 115.9 (d, JC–F 19.5, 17.6 ppm. IR (KBr, cmꢁ1): 2963, 2916, 2855, 2244, 1490,
¼ 23 Hz), 81.3, 80.2, 73.5, 73.3 ppm. IR (lm, cmꢁ1): 3070, 2924, 1456, 1378, 1274, 754, 689. HRMS (EI) calcd for C19H22 [M]+
2218, 1892, 1577, 1506, 1222, 830. HRMS (EI) calcd. for C15H8FN 250.1722; found 250.1739.
[M]+ 221.0641; found 221.0643.
2.25. Pale yellow liquid (0.065 g, 62%); Rf ¼ 0.38 (hexane). 1H
2.19.14 Colourless solid (0.067 g, 62%); mp 140–142 ꢀC, Rf ¼ NMR (400 MHz, CDCl3): d ¼ 7.42 (d, 2H, J ¼ 9.16 Hz, Ar–H), 6.82
0.30 (hexane). 1H NMR (400 MHz, CDCl3): d ¼ 7.48–7.45 (m, 4H, (d, 2H, J ¼ 8.68 Hz, Ar–H), 5.12–5.08 (m, 1H, –CH), 3.81 (s, 3H,
Ar–H), 7.35 (d, 2H, J ¼ 8.24 Hz, Ar–H), 6.86 (d, 2H, J ¼ 8.68 Hz, –OCH3), 2.35 (dd, 1H, J ¼ 16.96 Hz, 5.48 Hz, –CH), 2.25 (dd, 1H,
Ar–H), 3.82 (s, 3H, –OCH3), 1.31 (s, 9H, –C(CH3)3) ppm. 13C NMR J ¼ 16.96 Hz, 6.88 Hz, –CH), 2.03–1.96 (m, 2H, –CH), 1.77–1.72
(100 MHz, CDCl3): d ¼ 160.3, 152.5, 134.0, 132.2, 125.4, 118.9, (m, 1H, –CH), 1.69 (d, 3H, J ¼ 0.92 Hz, –CH3), 1.61 (s, 3H, –CH3),
114.1, 113.8, 81.4, 81.3, 73.5, 72.9, 55.3, 34.9, 31.1 ppm. IR (lm, 1.53–1.41 (m, 1H, –CH), 1.32–1.22 (m, 1H, –CH), 1.02 (d, 3H, J ¼
cmꢁ1): 2970, 2959, 2139, 1600, 1502, 1253, 830. HRMS (EI) calcd 6.4 Hz, –CH3) ppm. 13C NMR (100 MHz, CDCl3): d ¼ 160.0,
for C21H20O [M]+ 288.1514; found 288.1507.
134.0, 131.6, 124.3, 114.0, 83.0, 74.7, 73.2, 66.1, 55.3, 36.1, 32.2,
2.20.12 Pale yellow solid (0.054 g, 61%); mp 84–86 C. Rf ¼ 26.9, 25.7, 25.5, 19.5, 17.6 ppm. IR (KBr, cmꢁ1): 2961, 2915,
0.32 (hexane). 1H NMR (400 MHz, CDCl3): d ¼ 7.55–7.54 (m, 1H, 2144, 1604, 1509, 1459, 1288, 1250, 1173, 1032, 831. HRMS (EI)
Ar–H), 7.43 (d, 2H, J ¼ 8.92 Hz, Ar–H), 7.26–7.23 (m, 1H, Ar–H), calcd for C20H24O [M]+ 280.1827; found 280.1831.
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7.15–7.13 (m, 1H, Ar–H), 6.83 (d, 2H, J ¼ 8.96 Hz, Ar–H), 3.79 (s,
3.1. Pale yellow solid (0.086 g, 70%); mp 106–108 ꢀC. Rf ¼
3H, –OCH3) ppm. 13C NMR (100 MHz, CDCl3): d ¼ 160.3, 134.1, 0.29 (EtOAc/hexane, 1 : 4). 1H NMR (400 MHz, CDCl3): d ¼ 7.63
130.9, 130.2, 125.5, 121.1, 114.1, 113.7, 81.6, 76.2, 73.7, 72.7, (d, 2H, J ¼ 7.32 Hz, Ar–H), 7.39 (t, 2H, J ¼ 7.78 Hz, Ar–H), 7.31–
55.3 ppm. IR (lm, cmꢁ1): 2975, 2841, 2138, 1600, 1504, 1245, 7.27 (m, 2H, Ar–H), 7.22 (d, 1H, J ¼ 4.12 Hz, Ar–H), 6.84 (s, 2H,
1022, 831. HRMS (EI) calcd for C15H10OS [M]+ 238.0452; found Ar–H), 3.93 (s, 6H, –OCH3), 3.89 (s, 3H, –OCH3) ppm. 13C NMR
238.0450.
(100 MHz, CDCl3): d ¼ 153.5, 143.6, 143.4, 137.9, 134.2, 130.1,
2.21. Yellow solid (0.061 g, 51%); mp 110–112 C. Rf ¼ 0.37 128.9, 127.5, 125.5, 123.9, 103.2, 61.0, 56.2 ppm. IR (lm, cmꢁ1):
ꢀ
1
(hexane). H NMR (400 MHz, CDCl3): d ¼ 7.46 (d, 2H, J ¼ 9.16 3071, 2932, 1581, 1492, 1255, 1127, 758. HRMS (EI) calcd for
Hz, Ar–H), 7.25–7.19 (m, 3H, Ar–H), 7.03–7.00 (m, 2H, Ar–H),
6.85 (d, 2H, J ¼ 9.16 Hz, Ar–H), 3.82 (s, 3H, –OCH3) ppm. 13C
C
19H18O3S [M]+ 326.0977; found 326.0971.
3.2. Pale yellow solid (0.065 g, 51%); mp 118–120 ꢀC. Rf ¼
NMR (100 MHz, CDCl3): d ¼ 160.5, 140.0, 136.4, 135.0, 134.1, 0.33 (EtOAc/hexane, 1 : 4). 1H NMR (400 MHz, CDCl3): d ¼ 7.52
128.0, 125.4, 124.6, 123.5, 120.8, 114.2, 113.5, 84.6, 79.3, 74.0, (d, 2H, J ¼ 8.24 Hz, Ar–H), 7.24–7.19 (m, 4H, Ar–H), 6.83 (s, 2H,
72.6, 55.3 ppm. IR (lm, cmꢁ1): 3087, 2932, 2840, 2136, 1892, Ar–H), 3.93 (s, 6H, –OCH3), 3.88 (s, 3H, –OCH3), 2.38 (s, 3H,
1598, 1251, 800. HRMS (EI) calcd for C19H12OS2 [M]+ 320.0330; –CH3) ppm. 13C NMR (100 MHz, CDCl3): d ¼ 153.5, 143.6, 143.0,
found 320.0332.
137.8, 137.4, 131.4, 130.2, 129.6, 125.5, 123.8, 123.3, 103.1, 61.0,
78096 | RSC Adv., 2015, 5, 78090–78098
This journal is © The Royal Society of Chemistry 2015