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T.-jie Meng et al. / Tetrahedron 67 (2011) 8710e8716
OeCHHeCH, OeCH2eCH3), 3.89e3.83 (m, 5H; OeCHHeCH,
CH2eCHeCH, OeCH3), 1.25 (t, J¼6.9 Hz, 3H); 13C NMR (75 MHz,
CDCl3): 167.3, 158.9, 150.2, 143.4, 137.7, 131.5, 129.8, 120.2, 116.2,
114.1, 74.2, 71.4, 60.3, 55.2, 46.7, 14.2; FT-IR (neat): nmax 3078, 3034,
1714, 1633, 1286, 1246, 1174, 1101, 1064, 837 cmꢁ1; HRMS: calcd for
C19H23O4 [MþH]þ 315.1591; found 315.1580.
812 cmꢁ1; HRMS: calcd for C23H23N2O2S [MþH]þ 391.1475; found
391.1461.
4.2.16. Compound 3dd. White solid. Mp 135e137 ꢀC; 1H NMR
(300 MHz, CDCl3):
d
7.62 (d, J¼7.5 Hz, 2H; AreH), 7.42e7.06 (m,
13H; AreH, CeCHeCH), 5.97 (d, J¼15.9 Hz, 1H; CHeCHeC),
5.90e5.82 (m, 1H; CHeCHeCH2), 5.27e5.14 (m, 2H; CHeCH2),
3.82e3.77 (m, 2H; CH2eCHeCH, NeCHHeC), 3.50e3.38 (m, 3H;
NeCHHeC, NeCH2eCH), 2.44 (s, 3H; CeCH3); 13C NMR (75 MHz,
CDCl3): 143.7, 138.5, 137.8, 137.2, 136.9, 135.8, 132.2, 131.9, 129.7,
128.8, 128.7, 128.6, 127.9, 127.7, 127.5, 127.1, 126.4, 115.9, 53.9, 51.7,
44.8, 21.6; FT-IR (KBr): nmax 3076, 3027, 1597, 1336, 1153, 817, 750,
700 cmꢁ1; HRMS: calcd for C28H28NO2S [MþH]þ 442.1835; found
442.1792.
4.2.11. Compound 3cc. Yellow oil; 1H NMR (300 MHz, CDCl3):
d 7.52
(d, J¼15.9 Hz, 1H; CeCHeCH), 7.00 (d, J¼8.1 Hz, 2H; AreH), 6.92 (d,
J¼9.0 Hz, 2H; AreH), 5.97e5.86 (m, 1H; CHeCHeCH2), 5.26e5.21
(m, 2H; CHeCH2), 4.87 (d, J¼15.9 Hz, 1H; CHeCHeCN), 4.25 (d,
J¼16.2 Hz, 1H; OeCHHeC), 4.09e4.04 (m, 2H; OeCHHeC,
OeCHHeCH), 3.88e3.83 (m, 4H; OeCHHeCH, OeCH3), 3.78e3.73
(m, 1H; CH2eCHeCH); 13C NMR (75 MHz, CDCl3): 159.3, 151.4,
148.8, 137.3, 131.2, 129.8, 128.1, 118.7, 116.7, 114.4, 97.8, 74.3, 71.5,
55.3, 46.9; FT-IR (neat): nmax 3078, 3034, 2214, 1633, 1593, 1247,
4.2.17. Compound 3ea. White solid. Mp 122e124 ꢀC; 1H NMR
1105, 1064, 839 cmꢁ1
268.1332; found 268.1332.
;
HRMS: calcd for C17H18NO2 [MþH]þ
(300 MHz, CDCl3):
d
7.71 (d, J¼7.5 Hz, 2H; AreH), 7.43 (d, J¼15.9 Hz,
1H; CeCHeCH), 7.34 (d, J¼7.5 Hz, 2H; AreH), 5.83 (d, J¼15.9 Hz,1H;
CHeCHeCO), 5.77e5.69 (m, 1H; CHeCHeCH2), 5.08e5.03 (m, 2H;
CHeCH2), 4.09 (d, J¼15.9 Hz, 1H; NeCHHeC), 3.77e3.66 (m, 5H;
NeCHHeC, CH2eCHeCH, OeCH3), 3.45e3.41 (m, 1H; NeCHHeCH),
3.19e3.14 (m, 1H; NeCHHeCH), 2.44 (s, 3H; CeCH3), 2.08e2.04 (m,
2H; CeCH2eCH2), 1.31e1.30 (m, 4H; CH2eCH2eCH2eCH3), 0.90 (m,
3H; CH2eCH3); 13C NMR (75 MHz, CDCl3): 167.6, 144.1, 143.9, 141.4,
137.2, 132.0, 131.4, 129.7, 127.9, 117.2, 116.1, 53.5, 51.6, 50.8, 44.8,
30.4, 29.5, 22.9, 21.6, 13.9; FT-IR (KBr): nmax 3076, 3026, 1710, 1344,
1286, 1168, 1091, 817 cmꢁ1; HRMS: calcd for C22H30NO4S [MþH]þ
404.1890; found 404.1873.
4.2.12. Compound 3cd. Yellow oil; 1H NMR (300 MHz, CDCl3):
7.31e7.20 (m, 6H; CeCHeCH, AreH), 7.11 (d, J¼7.8 Hz, 2H; AreH),
d
6.95 (d, J¼6.9 Hz, 2H; AreH), 6.09e5.95 (m, 2H; CHeCHeCH2,
CHeCHeC), 5.35e5.21 (m, 2H; CHeCH2), 4.28 (d, J¼15.0 Hz, 1H;
OeCHHeC), 4.13e4.08 (m, 2H; OeCHHeC, OeCHHeCH), 3.86e3.82
(m, 5H; OeCHHeCH, CH2eCHeCH, OeCH3); 13C NMR (75 MHz,
CDCl3): 158.6, 141.8, 138.7, 137.6, 133.1, 131.3, 130.8, 130.1, 128.6,
128.5, 127.4, 126.4, 115.6, 113.9, 74.4, 71.4, 55.2, 46.7; FT-IR (neat):
nmax 3078, 3032,1635,1608,1246,1031,1107, 756, 694 cmꢁ1; HRMS:
calcd for C22H23O2 [MþH]þ 319.1693; found 319.1681.
4.2.18. Compound 3ec. White solid. Mp 105e106 ꢀC; 1H NMR
4.2.13. Compound 3da. White solid. Mp 151e152 ꢀC; 1H NMR
(300 MHz, CDCl3):
d
7.70 (d, J¼6.6 Hz, 2H; AreH), 7.34 (d,
(300 MHz, CDCl3):
d
7.69e7.58 (m, 3H; CeCHeCH, AreH), 7.36e7.26
J¼6.6 Hz, 2H; AreH), 7.11 (d, J¼16.8 Hz, 1H; CeCHeCH),
5.77e5.66 (m, 1H; CHeCHeCH2), 5.27 (d, J¼16.8 Hz, 1H;
CHeCHeCN), 5.09e4.96 (m, 2H; CHeCH2), 4.07 (d, J¼16.8 Hz, 1H;
NeCHHeC), 3.73 (d, J¼16.5 Hz, 1H; NeCHHeC), 3.55 (m, 1H;
CH2eCHeCH), 3.41e3.38 (m, 1H; NeCHHeCH), 3.19e3.14 (m, 1H;
NeCHHeCH), 2.43 (s, 3H; CeCH3), 2.04 (m, 2H; CeCH2eCH2), 1.29
(m, 4H; CH2eCH2eCH2eCH3), 0.90 (m, 3H; CH2eCH3); 13C NMR
(75 MHz, CDCl3): 146.9, 145.4, 144.2, 136.9, 131.8, 131.1, 129.8,
127.9, 118.5, 116.7, 95.7, 53.7, 51.0, 44.9, 30.2, 28.8, 22.9, 21.6, 13.9;
FT-IR (KBr): nmax 3084, 3034, 2210, 1631, 1595, 1346, 1157,
817 cmꢁ1; HRMS: calcd for C21H27N2O2S [MþH]þ 371.1788; found
371.1778.
(m, 5H; AreH), 6.98 (m, 2H; AreH), 5.85e5.79 (m, 1H;
CHeCHeCH2), 5.34 (d, J¼15.0 Hz, 1H; CHeCHeCO), 5.23e5.13 (m,
2H; CHeCH2), 3.85e3.79 (m, 2H; CH2eCHeCH, NeCHHeC), 3.67 (s,
3H; OeCH3), 3.47e3.41 (m, 2H; NeCHHeC, NeCHHeCH),
3.33e3.30 (m, 1H; NeCHHeCH), 2.43 (s, 3H; CeCH3); 13C NMR
(75 MHz, CDCl3): 167.4, 145.4, 143.9, 141.9, 136.9, 134.1, 132.1, 129.7,
128.9, 128.4, 128.0, 127.8, 120.8, 116.5, 53.6, 51.8, 51.6, 44.9, 21.6; FT-
IR (KBr): nmax 3084, 3034, 1712, 1633, 1598, 1344, 1284, 1157, 1089,
816 cmꢁ1; HRMS: calcd for C24H26NO4S [MþH]þ 424.1577; found
424.1574.
4.2.14. Compound 3db. White solid. Mp 134e135 ꢀC; 1H NMR
(300 MHz, CDCl3):
d
7.67 (d, J¼15.6 Hz, 1H; CeCHeCH), 7.60 (d,
4.2.19. Compound 3ed. White solid. Mp 90e91 ꢀC; 1H NMR
J¼7.2 Hz, 2H; AreH), 7.36e7.26 (m, 5H; AreH), 6.98 (d, J¼5.1 Hz,
2H; AreH), 5.85e5.79 (m, 1H; CHeCHeCH2), 5.33 (d, J¼15.6 Hz,1H;
CHeCHeCO), 5.23e5.13 (m, 2H; CHeCH2), 4.12 (d, J¼7.2 Hz, 2H;
OeCH2eCH3), 3.85e3.79 (m, 2H; CH2eCHeCH, NeCHHeC),
3.47e3.40 (m, 2H; NeCHHeC, NeCHHeCH), 3.34e3.29 (m, 1H;
NeCHHeCH), 2.43 (s, 3H; CeCH3), 1.22 (d, J¼6.6 Hz, 3H; CH2eCH3);
13C NMR (75 MHz, CDCl3): 166.9, 145.2, 143.9, 141.8, 137.0, 134.2,
132.1, 129.7, 128.9, 128.5, 127.9, 127.8, 121.3, 116.5, 64.4, 53.6, 51.8,
44.9, 21.6, 14.2; FT-IR (KBr): nmax 3076, 3026, 1712, 1340, 1284, 1176,
1157, 1091, 816, 705 cmꢁ1; HRMS: calcd for C25H28NO4S [MþH]þ
438.1734; found 438.1702.
(300 MHz, CDCl3):
d
7.73 (d, J¼6.6 Hz, 2H; AreH), 7.36e7.17 (m, 7H;
AreH), 6.85 (d, J¼16.2 Hz, 1H; CeCHeCH), 6.49 (d, J¼16.2 Hz, 1H;
CHeCHeC), 5.84e5.72 (m, 1H; CHeCHeCH2), 5.12e5.04 (m, 2H;
CHeCH2), 4.08 (d, J¼15.0 Hz,1H; NeCHHeC), 3.78 (d, J¼15.0 Hz,1H;
NeCHHeC), 3.66e3.61 (m, 1H; CH2eCHeCH), 3.42e3.37 (m, 1H;
NeCHHeCH), 3.23e3.17 (m, 1H; NeCHHeCH), 2.43 (s, 3H;
CeCH3), 2.23e2.15 (m, 2H; CeCH2eCH2), 1.41e1.32 (m, 4H;
CH2eCH2eCH2eCH3), 0.93 (m, 3H; CH2eCH3); 13C NMR (75 MHz,
CDCl3): 143.8, 138.1, 137.6, 135.8, 132.9, 132.3, 129.7, 128.7, 127.9,
127.5, 126.3, 126.1, 115.5, 53.8, 50.8, 44.8, 30.8, 29.6, 23.0, 21.6, 14.0;
FT-IR (KBr): nmax 3084, 3034, 2210, 1631, 1597, 1344, 1157, 707 cmꢁ1
.
HRMS: calcd for C26H32NO2S [MþH]þ 422.2148; found 422.2145.
4.2.15. Compound 3dc. White solid. Mp 150e151 ꢀC; 1H NMR
(300 MHz, CDCl3):
d
7.60 (d, J¼7.5 Hz, 2H; AreH), 7.39e7.26 (m, 6H;
4.2.20. Compound 3fa. Yellow oil; 1H NMR (300 MHz, CDCl3):
AreH, CeCHeCH), 6.97 (d, J¼6.4 Hz, 2H; AreH), 5.84e5.75 (m, 1H;
CHeCHeCH2), 5.20e5.15 (m, 2H; CHeCH2), 4.78 (d, J¼15.9 Hz, 1H;
CHeCHeCN), 3.82e3.69 (m, 2H; CH2eCHeCH, NeCHHeC),
3.47e3.30 (m, 3H; NeCHHeC, NeCH2eCH,), 2.44 (s, 3H; CeCH3);
13C NMR (75 MHz, CDCl3): 147.3, 146.6, 144.1, 136.6, 135.4, 133.8,
131.9, 129.8, 129.3, 128.6, 128.5, 127.9, 118.2, 117.1, 99.1, 53.8, 51.9,
45.1, 21.6; FT-IR (KBr): nmax 3084, 3034, 2214, 1597, 1344, 1157,
d
7.78 (d, J¼15.9 Hz, 1H; CeCHeCH), 7.35e7.27 (m, 3H; AreH), 7.09
(m, 2H; AreH), 5.98e5.87 (m, 1H; CHeCHeCH2), 5.42 (d, J¼15.9 Hz,
1H; CHeCHeCO), 5.24e5.16 (m, 2H; CHeCH2), 4.05e3.92 (m, 2H;
NeCH2eC), 3.70e3.54 (m, 6H; NeCH2eCH, CH2eCHeCH, OeCH3),
1.42 (s, 9H; C(CH3)3); 13C NMR (75 MHz, CDCl3): 167.6, 154.4, 147.1,
142.4, 137.9, 137.3, 133.4, 128.8, 128.7, 127.8, 120.4, 115.5, 79.8, 51.5,
49.9, 44.8, 43.8, 28.4; FT-IR (neat): nmax 3093, 3062, 2978, 1714,