2418
L. Zhu et al. / Tetrahedron 68 (2012) 2414e2420
6.82 (d, J¼7.5 Hz, 1H, Ar), 5.82 (s, 1H), 2.32 (s, 3H, Me). 13C NMR
4.2.29. Compound 4ac. A white solid. Mp: 105e107 ꢀC 1H NMR
(75 MHz, CDCl3)
d
141.8, 141.7, 140.0, 139.9, 139.5, 129.3, 123.7, 123.4,
(300 MHz, CDCl3, TMS) d 7.10e6.98 (m, 6H, Ar), 4.87 (br, 1H), 3.08
122.9, 118.9, 115.3, 21.5.
(hep, J¼6.6 Hz, 4H), 1.09 (d, J¼6.6 Hz, 24H, 8Me). 13C NMR
(125 MHz, CDCl3)
d 140.9, 140.4, 123.8, 122.7, 27.8, 23.5. IR (neat) n
4.2.19. Compound 4s.20 A white solid. 1H NMR (300 MHz, CDCl3,
3724, 3629, 3600, 2948, 2864, 2357, 2335, 1748, 1731, 1537, 1455,
TMS)
d
8.25 (d, J¼2.4 Hz,1H, Ar), 8.07 (d, J¼4.5 Hz,1H, Ar), 7.27e7.19
1441,1332,1270,1250,1104,1045, 931, 888, 864, 786, 741, 668 cmꢁ1
.
(m, 1H, Ar), 7.13e7.10 (m, 3H, Ar), 6.89 (d, J¼9.0 Hz, 2H, Ar), 5.58 (s,
MS (ESI, m/z): 338 [Mþ1]þ; HRMS (EI): calcd for C24H36N [M]þ:
1H), 3.81 (s, 3H, OMe). 13C NMR (75 MHz, CDCl3)
140.6, 138.3, 134.3, 123.7, 122.7, 121.1, 114.8, 55.5.
d
155.9, 141.6,
338.2847; found: 338.2842.
4.2.30. Compound 4ad.8b A white solid. 1H NMR (500 MHz, CDCl3,
4.2.20. Compound 4t.21 A white solid. 1H NMR (500 MHz, CDCl3,
TMS)
7.19e7.09 (m, 5H, Ar), 6.77 (t, J¼7.0 Hz, 1H, Ar), 6.54e6.52
(m, 2H, Ar), 5.21 (br, 1H), 2.24 (s, 6H, 2Me). 13C NMR (125 MHz,
CDCl3) 146.2, 138.2, 135.9, 129.2, 128.5, 125.7, 118.2, 113.5, 18.3.
TMS)
2.26 (s, 3H, Me), 2.00 (s, 6H, 2Me), 1.99 (s, 6H, 2Me). 13C NMR
(125 MHz, CDCl3) 142.2, 139.0, 131.5, 130.5, 129.2, 128.8, 128.5,
120.9, 20.6, 19.1, 19.0.
d
6.96 (d, J¼7.5 Hz, 2H, Ar), 6.81e6.78 (m, 3H, Ar), 4.71 (s, 1H),
d
d
d
4.2.21. Compound 4u.16 A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
4.2.31. Compound 4ae.24 A white solid. 1H NMR (500 MHz, CDCl3,
d
7.30 (dd, J¼8.5, 7.0 Hz, 1H, Ar), 7.22 (d, J¼7.5 Hz, 2H,
TMS) d 6.78 (s, 4H, Ar), 4.60 (s, 1H), 2.24 (s, 6H, 2Me), 1.97 (s,
Ar), 7.14 (dd, J¼8.5, 7.5 Hz, 2H, Ar), 6.71 (t, J¼7.5 Hz, 1H, Ar), 6.48 (d,
12H, 4Me). 13C NMR (125 MHz, CDCl3)
20.5, 19.0.
d 139.5, 130.7, 129.4, 129.3,
J¼7.5 Hz, 2H, Ar), 3.20 (hep, J¼7.0 Hz, 2H), 1.14 (d, J¼7.0 Hz, 12H,
4Me). 13C NMR (125 MHz, CDCl3)
123.8, 117.6, 112.9, 28.2, 23.8.
d 148.1, 147.6, 135.1, 129.2, 127.2,
4.2.32. Compound 4af.25 A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
d
7.30 (d, J¼9.0 Hz, 2H, Ar), 7.19 (dd, J¼8.5, 7.5 Hz, 2H,
4.2.22. Compound 4v.14 A pale yellow liquid. 1H NMR (500 MHz,
DMSO)
7.04 (t, J¼7.5 Hz, 2H, Ar), 6.91 (s, 2H, Ar), 6.55 (t, J¼7.5 Hz,
Ar), 6.89 (d, J¼9.0 Hz, 2H, Ar), 6.72 (t, J¼7.5 Hz, 1H, Ar), 6.65 (d,
d
J¼7.5 Hz, 2H, Ar), 4.26 (s, 2H), 3.81 (s, 3H, OMe). 13C NMR
1H, Ar), 6.36 (d, J¼7.5 Hz, 2H, Ar), 2.23 (s, 3H, Me), 2.07 (s, 6H, 2Me).
(500 MHz, CDCl3)
112.8, 55.3, 47.8.
d 158.9, 148.2, 131.4, 129.2, 128.8, 117.5, 114.0,
13C NMR (125 MHz, DMSO)
116.3, 112.2, 20.5, 18.0.
d 147.2, 135.8, 135.6, 134.3, 129.0, 128.9,
4.2.33. Compound 4ag.9g A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
7.40e7.26 (m, 5H, Ar), 7.20 (dd, J¼8.0, 7.5 Hz, 2H, Ar),
4.2.23. Compound 4w.21 A white solid. 1H NMR (500 MHz, CDCl3,
TMS)
d
d
7.11 (d, J¼7.5 Hz, 1H, Ar), 7.10e6.94 (m, 3H, Ar), 6.67 (t,
6.74 (t, J¼7.5 Hz, 1H, Ar), 6.66 (d, J¼8.0 Hz, 2H, Ar), 4.35 (s, 2H), 4.04
J¼7.5 Hz, 1H, Ar), 6.13 (d, J¼8.0 Hz, 1H, Ar), 4.85 (s, 1H), 2.31 (s, 3H,
(s, 1H). 13C NMR (500 MHz, CDCl3)
127.2, 117.6, 112.8, 48.3.
d 148.1, 139.4, 129.2, 128.6, 127.5,
Me), 2.30 (s, 3H, Me), 2.14 (s, 6H, 2Me). 13C NMR (125 MHz, CDCl3)
d
144.5, 136.0, 135.6, 135.1, 130.2, 129.2, 126.9, 122.1, 117.8, 111.5,
20.9, 18.1, 17.6.
4.2.34. Compound 4ah.9g A yellow liquid. 1H NMR (500 MHz, CDCl3,
TMS)
d
7.15 (t, J¼7.5 Hz, 2H, Ar), 6.66 (t, J¼7.5 Hz, 1H, Ar), 6.59 (d,
4.2.24. Compound 4x.22 A white solid. 1H NMR (500 MHz, CDCl3,
TMS)
J¼7.5 Hz, 1H, Ar), 6.15 (d, J¼8.0 Hz, 1H, Ar), 4.94 (s, 1H), 2.34 (s, 3H,
Me), 2.19 (s, 6H, 2Me). 13C NMR (125 MHz, CDCl3)
144.1, 138.7,
J¼7.5 Hz, 2H, Ar), 3.51 (br, 1H), 3.28e3.23 (m, 1H), 2.07e2.05 (m,
2H), 1.78e1.74 (m, 2H), 1.67e1.64 (m, 1H), 1.42e1.33 (m, 2H),
d
7.14e7.07 (m, 4H, Ar), 6.97 (t, J¼7.5 Hz, 1H, Ar), 6.71 (t,
1.26e1.14 (m, 3H). 13C NMR (500 MHz, CDCl3)
d 147.4, 129.2, 116.8,
d
113.1, 51.7, 33.5, 25.9, 25.0.
135.5, 130.2, 128.5, 126.9, 125.5, 122.5, 118.1, 111.8, 18.2, 17.6.
4.2.35. Compound 4ai.26 A yellow liquid. 1H NMR (500 MHz, CDCl3,
TMS)
4.2.25. Compound 4y.21 A pale yellow liquid. 1H NMR (300 MHz,
d
7.05 (t, J¼8.0 Hz, 1H, Ar), 6.24e6.19 (m, 2H, Ar), 6.14 (t,
CDCl3, TMS)
d
7.30e7.21 (m, 3H, Ar), 7.12 (d, J¼7.5 Hz, 1H, Ar), 6.94
J¼2.5 Hz, 1H, Ar), 3.76 (s, 3H, OMe), 3.26e3.20 (m, 1H), 2.07e2.04
(t, J¼8.0 Hz, 1H, Ar), 6.66 (t, J¼7.5 Hz, 1H, Ar), 6.11 (d, J¼8.0 Hz, 1H,
Ar), 4.89 (s, 1H), 3.10 (hep, J¼6.6 Hz, 2H), 2.34 (s, 3H, Me), 1.16 (d,
J¼6.6 Hz, 6H, 2Me), 1.11 (d, J¼6.6 Hz, 6H, 2Me). 13C NMR (125 MHz,
(m, 2H), 1.77e1.73 (m, 2H), 1.66e1.62 (m, 1H), 1.40e1.32 (m, 2H),
1.27e1.10 (m, 3H). 13C NMR (500 MHz, CDCl3)
d 160.9, 148.8, 129.9,
106.4, 101.8, 99.1, 55.1, 51.7, 33.5, 25.9, 25.0.
CDCl3)
d 147.3, 146.0, 135.7, 130.1, 127.03, 126.95, 123.8, 121.3, 117.5,
111.4, 28.2, 24.7, 23.0, 17.6.
4.2.36. Compound 4aj.9g A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
d
7.17 (t, J¼7.5 Hz, 2H, Ar), 6.68 (t, J¼7.5 Hz, 1H, Ar), 6.60
4.2.26. Compound 4z.22 A white solid. 1H NMR (500 MHz, CDCl3,
(d, J¼7.5 Hz, 2H, Ar), 3.59 (s, 1H), 3.10 (t, J¼7.0 Hz, 2H), 1.63e1.56 (m,
TMS)
d
6.97 (d, J¼7.5 Hz, 4H, Ar), 6.84 (t, J¼7.5 Hz, 2H, Ar), 4.79 (s,
2H), 1.41e1.26 (m, 10H), 0.89 (t, J¼6.5 Hz, 3H). 13C NMR (125 MHz,
1H), 2.01 (s, 12H, 4Me). 13C NMR (125 MHz, CDCl3)
128.7, 121.7, 19.1.
d
141.8, 129.6,
CDCl3) d 148.4, 129.2, 117.3, 112.9, 44.2, 31.8, 29.5, 29.4, 29.3, 27.2,
22.6, 14.1.
4.2.27. Compound 4aa.23 A yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
4.2.37. Compound 4ak.27 A pale yellow liquid. 1H NMR (500 MHz,
d
7.16e7.11 (m, 3H, Ar), 6.94 (d, J¼7.5 Hz, 2H, Ar),
CDCl3, TMS)
d
6.99 (d, J¼8.0 Hz, 2H, Ar), 6.54 (d, J¼8.0 Hz, 2H, Ar),
6.72 (t, J¼7.5 Hz, 1H, Ar), 4.79 (s, 1H), 3.15 (hep, J¼7.0 Hz, 2H), 1.98
3.08 (t, J¼7.0 Hz, 2H), 2.24 (s, 3H, Me), 1.63e1.58 (m, 2H), 1.42e1.23
(s, 6H, 2Me), 1.12 (d, J¼7.0 Hz, 12H, 4Me). 13C NMR (125 MHz,
(m, 10H), 0.89 (t, J¼7.0 Hz, 3H). 13C NMR (125 MHz, CDCl3)
d 146.3,
CDCl3)
d
144.1, 143.1, 138.8, 129.5, 125.7, 124.8, 123.2, 119.6, 28.0,
129.7, 126.3, 112.9, 44.4, 31.8, 29.6, 29.4, 29.3, 27.2, 22.6, 20.3, 14.1.
23.4, 19.3.
4.2.38. Compound 4al. A pale yellow liquid. 1H NMR (500 MHz,
4.2.28. Compound 4ab.24 A yellow liquid. 1H NMR (300 MHz, CDCl3,
CDCl3, TMS)
d
7.06 (t, J¼7.5 Hz, 1H, Ar), 6.52 (d, J¼7.5 Hz, 1H, Ar),
TMS)
J¼6.9 Hz, 2H), 2.22 (s, 3H, Me), 1.95 (s, 6H, 2Me), 1.11 (d, J¼6.9 Hz,
12H, 4Me). 13C NMR (125 MHz, CDCl3)
143.4, 140.5, 139.2, 130.0,
129.1, 126.4, 124.2, 123.2, 28.0, 23.4, 20.4, 19.2.
d
7.09 (s, 3H, Ar), 6.75 (s, 2H, Ar), 4.69 (s, 1H), 3.12 (hep,
6.44 (d, J¼7.5 Hz, 2H, Ar), 3.09 (t, J¼7.0 Hz, 2H), 2.28 (s, 3H, Me),
1.64e1.58 (m, 2H), 1.31e1.26 (m, 10H), 0.89 (t, J¼6.5 Hz, 3H). 13C
d
NMR (125 MHz, CDCl3) d 148.6, 139.0, 129.1, 118.0, 113.5, 109.9, 44.1,
31.8, 29.6, 29.4, 29.3, 27.2, 22.6, 21.6, 14.1. IR (neat)
n 3418, 3389,