171.9. MS (EI) m/z: 232 [M+], 203, 171, 159 (100), 144, 131, 118,
85, 77, 63, 55. Anal. calcd. for C13H16N2O2 (232.28): C, 67.22; H,
6.94; N, 12.06. Found: C, 67.14; H, 7.06; N, 12.18.
(372.46): C, 77.39; H, 6.49; N, 7.52. Found: C, 77.25; H, 6.59;
N, 7.71.
14a. Yield 72%. Yellow oil. IR (neat) nmax/cm-1: 752, 923, 1034,
1
13f. Diastereomeric mixture 60 : 40, Yield 60%. 13fa. Yield 36%.
Yellow oil. IR (neat) nmax/cm-1: 752, 908, 1160, 1465, 1616, 1654,
1758, 3027, 3062, 3086. 1H NMR (400 MHz, CDCl3) d: 2.28–2.43
(m, 1H), 2.49–2.61 (m, 2H), 2.77–2.93 (m, 1H), 4.43–4.51 (m, 1H),
5.42 (dt, 1H, J = 1.7, 7.3 Hz), 5.96 (dd, 1H, J = 1.7, 5.6 Hz), 6.96–
7.01 (m, 3H), 7.15–7.26 (m, 5H), 7.36–7.41 (m, 1H), 7.73–7.77 (m,
1H), 8.10 (s, 1H). 13C NMR (100 MHz, CDCl3) d: 31.9, 33.3, 59.7,
85.0, 109.2, 121.5, 121.6, 122.5, 124.0, 126.5, 127.2, 128.7, 134.9,
140.3, 140.8, 154.0, 172.3. MS (EI) m/z: 318 [M+], 235, 200, 117,
91 (100), 65, 39. Anal. calcd. for C20H18N2O2 (318.37): C, 75.45;
H, 5.70; N, 8.80. Found: C, 75.55; H, 5.81; 8.97. 13fb. Yield 24%.
Yellow oil. IR (neat) nmax/cm-1: 751, 908, 1159, 1467, 1614, 1654,
1786, 3025, 3060, 3085. 1H NMR (400 MHz, CDCl3) d: 2.07–2.18
(m, 1H), 2.25–2.37 (m, 1H), 2.43–2.53 (m, 1H), 2.54–2.67 (m, 1H),
4.79–4.86 (m, 1H), 5.25 (dt, 1H, J = 1.7, 4.7 Hz), 6.11 (dd, 1H, J =
1.7, 5.6 Hz), 6.95–7.00 (m, 2H), 7.14–7.28 (m, 4H), 7.32 (dd, 1H,
J = 0.9, 8.5 Hz), 7.38–7.45 (m, 1H), 7.69 (dd, 1H, J = 1.7, 5.6 Hz),
7.76 (dt, 1H, J = 0.9, 8.1 Hz), 8.11 (s, 1H). 13C NMR (100 MHz,
CDCl3) d: 30.4, 31.9, 58.6, 84.5, 109.2, 121.5, 123.0, 124.2, 126.5,
127.1, 128.6, 128.7, 128.8, 130.0, 134.8, 140.3, 154.1, 172.4. MS
(EI) m/z: 318 [M+], 235, 200, 117, 91 (100), 65, 39. Anal. calcd. for
C20H18N2O2 (318.37): C, 75.45; H, 5.70; N, 8.80. Found: C, 75.68;
H, 5.64; N, 8.91.
1173, 1215, 1484, 1582, 1624, 1707, 3409. H NMR (400 MHz,
CDCl3) d: 0.83 (t, 3H, J = 7.3 Hz), 1.16–1.32 (m, 6H), 1.60–1.82
(m, 2H), 2.03 (s, 3H), 2.74–2.91 (m, 2H), 3.37–3.48 (m, 1H), 3.88
(s, 3H), 6.85 (dd, 1H, J = 2.6, 8.6 Hz), 6.93 (s, 1H), 7.09 (d, 1H,
J = 2.6 Hz), 7.23 (d, 1H, J = 9.0 Hz), 8.00 (bs, 1H). 13C NMR
(100 MHz, CDCl3) d: 14.3, 22.8, 27.4, 30.7, 32.0, 32.9, 35.9, 50.3,
56.2, 101.6, 111.9, 112.1, 118.9, 122.2, 127.2, 131.9, 153.8, 209.3.
MS (EI) m/z: 287 [M+], 244, 230, 216, 174, 160 (100), 130, 43.
Anal. calcd. for C18H25NO2 (287.40): C, 75.22; H, 8.77; N, 4.87.
Found: C, 75.31; H, 8.69; N, 4.95.
14b. Yield 70%. Yellow solid, m.p. 84-87 ◦C. IR (nujol)
n
max/cm-1: 740, 918, 1208, 1463, 1635, 1679. 1H NMR (400 MHz,
CDCl3) d: 0.80 (t, 3H, J = 7.3 Hz), 1.81–2.04 (m, 2H), 2.37 (s, 3H),
3.40 (dd, 1H, J = 6.0, 15.4 Hz), 3.45–3.54 (m, 1H), 3.58 (dd, 1H,
J = 6.4, 15.4 Hz), 3.61 (s, 3H), 7.03–7.08 (m, 1H), 7.10–7.16 (m,
1H), 7.23 (d, 1H, J = 8.1 Hz), 7.37 (t, 2H, J = 7.7 Hz), 7.44–7.51
(m, 1H), 7.67 (d, 1H, J = 7.7 Hz), 7.83–7.87 (m, 2H). 13C NMR
(100 MHz, CDCl3) d: 10.6, 12.9, 28.4, 29.7, 35.2, 44.8, 109.0, 112.9,
118.5, 119.2, 120.3, 127.8, 128.2, 128.5, 129.9, 132.8,136.7, 137.2,
200.3. MS (EI) m/z: 305 [M+], 276, 186 (100), 171, 105, 77. Anal.
calcd. for C21H23NO (305.41): C, 82.58; H, 7.59; N, 4.59. Found:
C, 82.36; H, 7.74; N, 5.51.
14c. Yield 67%. Yellow oil. IR (neat) nmax/cm-1: 1377, 1460,
1
13g. Yield 51%. Yellow oil. IR (neat) nmax/cm-1: 741, 785, 912,
1698, 3361. H NMR (400 MHz, CDCl3) d: 0.81 (t, 3H, J =
1
1022, 1173, 1219, 1421, 1464, 1616, 3061, 3102 cm-1. H NMR
6.8 Hz), 0.97 (s, 9H), 1.07–1.33 (m, 6H), 1.60–1.75 (m, 1H), 1.81–
1.96 (m 1H), 2.39 (s, 3H), 2.86 (dd, 1H, J = 6.4, 16.7 Hz), 3.11 (dd,
1H, J = 7.7, 17.1 Hz), 3.39–3.50 (m, 1H), 7.01–7.13 (m, 2H), 7.25
(400 MHz, CDCl3) d: 0.87 (t, 3H, J = 7.7 Hz), 2.20 (s, 3H), 2.31–
2.57 (m, 2H), 5.55 (dd, 1H, J = 6.0, 9.4 Hz), 5.87–5.90 (m, 1H),
6.17 (d, 1H, J = 3.0 Hz), 7.11–7.16 (m, 1H), 7.32–7.37 (m, 1H),
(d, 1H, J = 8.6 Hz), 7.61 (d, 1H, J = 7.3 Hz), 7.74 (bs, 1H). 13
C
7.48 (dd, 1H, J = 0.9, 8.5 Hz), 7.71–7.43 (m, 1H), 8.04 (s, 1H). 13
C
NMR (100 MHz, CDCl3) d: 12.2, 14.3, 22.8, 26.3, 28.0, 32.0, 32.4,
35.0, 42.7, 44.4, 110.6, 114.0, 118.9, 119.3, 120.6, 127.4, 131.7,
135.8, 215.7. MS (EI) m/z: 313 [M+], 242, 214 (100), 157, 144, 130,
85, 57, 41, 29. Anal. calcd. for C21H31NO (313.48): C, 80.46; H,
9.97; N, 4.47. Found: C, 80.65; H, 10.11; N, 4.61.
NMR (100 MHz, CDCl3) d: 11.2, 13.8, 26.1, 58.9, 106.4, 108.1,
109.7, 120.7, 121.3, 124.4, 126.2, 133.4, 139.7, 151.6, 152.0. (EI)
m/z: 240 [M+], 211, 123 (100), 107, 95, 77, 43. Anal. calcd. for
C15H16N2O (240.30): C, 74.97; H, 6.71; N, 11.66. Found: 74.85; H,
6.84, N, 11.79.
14d. Diastereomeric mixture 50 : 50. Yield 80%. Colorless oil.
IR (neat) nmax/cm-1: 738, 1377, 1458, 1618, 1700, 3411. 1H NMR
(400 MHz, CDCl3) d: 0.75 (t, 1.5H, J = 7.7 Hz), 0.87 (t, 1.5H, J =
7.7 Hz), 1.28–2.08 (m, 8H), 2.15–2.27 (m, 0.5H), 2.31–2.53 (m,
1.5H), 2.61–2.70 (m, 0.5H), 2.74–2.85 (m, 0.5H), 3.17–3.27 (m,
0.5H), 3.53–3.61 (m, 0.5H), 6.99 (d, 0.5H, J = 2.1 Hz), 7.01 (d,
0.5H, J = 2.1 Hz), 7.07–7.14 (m, 1H), 7.15–7.22 (m, 1H), 7.33–7.40
(m, 1H), 7.58 (d, 0.5H, J = 7.7 Hz), 7.66 (d, 0.5H, J = 7.7 Hz), 8.05
(bs, 1H). 13C NMR (100 MHz, CDCl3) d: 12.8, 12.9, 24.0, 24.2,
24.7, 27.3, 27.9, 29.0, 29.1, 32.8, 36.3, 38.8, 42.3, 42.4, 55.5, 56.6,
111.4, 111.5, 117.0, 117.9, 119.1, 119.3, 119.4, 120.0, 122.0, 122.2,
122.8, 127.5, 127.8, 136.5, 136.8, 213.1, 214.9. MS (EI) m/z: 255
[M+], 158 (100), 130, 115, 77. Anal. calcd. for C17H21NO (255.35):
C, 79.96; H, 8.29; N, 5.49. Found: C, 80.18; H,8.41; N, 5.57.
14e. Yield 61%. Yellow oil. IR (neat) nmax/cm-1: 771, 917, 1377,
1459, 1718, 3327. 1H NMR (400 MHz, CDCl3) d: 0.78 (s, 3H), 0.82
(t, 3H, J = 7.3 Hz), 1.08 (s, 3H), 1.17–1.39 (m, 6H), 1.51–1.63 (m,
1H), 2.20–2.34 (m, 1H), 3.34 (dd, 1H, J = 3.4, 12.4 Hz), 7.08–7.14
(m, 1H), 7.16–7.22 (m, 1H), 7.36 (d, 1H, J = 8.1 Hz), 7.39–7.51
13h. Yield 63%. Yellow oil. IR (neat) nmax/cm-1: 738, 1045, 1112,
1158, 1375, 1460, 1619, 1731. 1H NMR (400 MHz, CDCl3) d: 1.12–
1.31 (m, 2H), 1.37–1.48 (m, 2H), 1.60–1.71 (m, 2H), 2.15–2.27 (m,
1H), 2.52–2.65 (m, 1H), 3.40 (t, 2H, J = 6.8 Hz), 3.67 (s, 3H), 5.45
(dd, 1H, J = 6.0, 9.4 Hz), 6.73 (d, 2H, J = 9.0 Hz), 7.01–7.07 (m,
1H), 7.20 (d, 2H, J = 9.0 Hz), 7.21–7.27 (m, 1H), 7.32 (d, 1H,
J = 8.5 Hz), 7.64 (d, 1H, J = 8.1 Hz), 7.98 (s, 1H). 13C NMR
(100 MHz, CDCl3) d: 26.0, 26.5, 32.3, 35.0, 45.0, 55.2, 62.0, 109.3,
113.9, 120.6, 121.1, 124.2, 126.1, 127.9, 133.0, 133.3, 139.5, 159.0.
(EI) m/z: 344 [M+2+], 342 [M+], 237, 225, 121 (100), 91, 77, 41.
Anal. calcd. for C20H23ClN2O (342.86): C, 70.06; H, 6.76; N, 8.17.
Found: C, 70.30; H, 6.89; N, 8.02.
13i. Yield 77%. Colorless waxy solid. IR (neat) nmax/cm-1: 740,
1
1040, 1116, 1157, 1377, 1462, 1616, 1732. H NMR (400 MHz,
CDCl3) d: 2.45–2.68 (m, 3H), 2.92–3.04 (m, 1H), 3.74 (s, 3H),
3.79 (s, 3H), 6.02 (dd, 1H, J = 5.1, 10.3 Hz), 6.41 (s, 1H), 7.08–
7.14 (m, 3H), 7.15–7.21 (m, 1H), 7.22–7.35 (m, 5H), 7.40 (d,
1H, J = 8.5 Hz), 7.71 (d, 1H, J = 8.1 Hz), 8.09 (s, 1H). 13C
NMR (100 MHz, CDCl3) d: 33.0, 36.3, 53.8, 55.5, 55.6, 98.4,
104.6, 109.9, 120.6, 120.9, 122.3, 124.0, 125.9, 126.0, 128.2, 128.4,
128.7, 133.3, 140.1, 141.7, 157.3, 160.3. (EI) m/z: 372 [M+], 267,
255, 151 (100), 121, 91, 77, 65. Anal. calcd. for C24H24N2O2
(m, 5H), 7.72 (d, 1H, J = 8.1 Hz), 8.10 (bs, 1H), 9.32 (s, 1H). 13
C
NMR (100 MHz, CDCl3) d: 14.3, 19.9, 21.5, 22.7, 28.7, 29.2, 32.4,
42.4, 52.1, 111.1, 111.2, 119.7, 122.0, 122.2, 128.0, 128.4, 129.0,
129.8, 133.9, 136.4, 138.0, 207.5. MS (EI) m/z: 347 [M+], 276, 217,
This journal is
The Royal Society of Chemistry 2010
Org. Biomol. Chem., 2010, 8, 706–712 | 711
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