1958
M. Periasamy et al. / Tetrahedron Letters 48 (2007) 1955–1958
124.6, 110.5, 44.5, 12.3. Compound 1d: 1H NMR: Compound 5d: 1H NMR: (200 MHz, d ppm, CDCl3)
(200 MHz, ppm, CDCl3) 9.98 (s, 1H,), 7.68 (d,
d
8.06 (d, J = 8.8 Hz, 2H), 7.66 (d, J = 8.8 Hz, 2H), 7.55 (d,
J = 6.8 Hz, 2H), 7.31–7.17 (m, 4H), 6.71 (d, J = 8.6 Hz,
4H), 6.47 (d, J = 8.8 Hz, 4H), 6.22 (d, J = 8.8 Hz, 4H),
4.89 (br s, 1H), 4.76 (br s, 1H), 2.88 (t, J = 6.0 Hz, 8H),
J = 9.0 Hz, 2H), 6.64 (d, J = 8.8 Hz, 2H), 3.54–3.28 (m,
4H), 1.70–1.48 (m, 2H), 1.46–1.20 (m, 2H), 1.18 (t,
J = 6.8 Hz, 3H), 0.95 (t, J = 7.2 Hz, 3H); 13C NMR:
(50 MHz, d ppm, CDCl3) 189.8, 152.4, 132.2, 124.6, 110.6,
50.2, 45.1, 29.5, 20.2, 13.9, 12.2, mass GC–MS (m/z) 205
(M+). Compound 2a: 1H NMR: (200 MHz, d ppm,
CDCl3) 7.50–6.70 (m, 9H), 4.23 (q, J = 7.2 Hz, 1H), 3.52
(q, J = 6.8 Hz, 4H), 1.75 (d, J = 7.2 Hz, 3H) 1.32 (t,
J = 6.8 Hz, 6H); 13C NMR: (50 MHz, d ppm, CDCl3)
147.5, 146.6, 133.5, 128.4, 128.3, 127.7, 125,5, 112.2, 44.5,
43.9, 22.2, 12.8. Compound 3a: 1H NMR: (200 MHz, d
ppm, CDCl3) 7.50–6.90 (m, 13H), 5.70 (s, 1H), 3.60 (q,
J = 6.8 Hz, 8H), 1.50 (t, J = 6.8 Hz, 12H); 13C NMR:
(50 MHz, d ppm, CDCl3) 146.4, 146.0, 132.1, 130.4, 129.7,
128.3, 125.9, 112.1, 55.4, 44.6, 13.0. Compound 3b: 1H
NMR: (200 MHz, d ppm, CDCl3) 7.30–6.60 (m, 13H),
4.15 (t, J = 6.8 Hz, 1H), 3.45–3.25 (m, 10H), 1.25 (t,
J = 6.8 Hz, 12H); 13C NMR: (50 MHz, d ppm, CDCl3)
146.2, 141.4, 132.8, 129.2, 128.7, 127.9, 125.7, 112.3, 51.1,
44.4, 42.8, 12.7, mass (EI) (m/z) 400 (M+). Compound 5a:
1H NMR: (200 MHz, d ppm, CDCl3) 7.32–7.06 (m, 14H),
6.56 (d, J = 8.8 Hz, 4H), 4.79 (d, J = 11.7 Hz, 1H), 4.67
(d, J = 11.7 Hz, 1H), 3.32 (q, J = 6.8 Hz, 8H), 1.19 (t,
J = 6.8 Hz, 12H); 13C NMR: (50 MHz, d ppm, CDCl3)
148.8, 144.5, 131.8, 129.1, 128.6, 127.9, 125.4, 112.2, 56.9,
54.2, 44.2, 12.5. Compound 5b: 1H NMR: (200 MHz, d
ppm, CDCl3) 6.36–6.08 (m, 14H), 5.78 (d, J = 8.6 Hz,
4H), 4.84 (d, J = 11.7 Hz, 1H), 4.72 (d, J = 11.7 Hz, 1H),
2.21 (t, J = 5.0 Hz, 8H), 0.80–0.62 (m, 12H); 13C NMR:
(50 MHz, d ppm, CDCl3) 149.9, 144.0, 134.9, 128.8, 128.5,
127.9, 116.2, 56.7, 54.6, 50.6, 25.9, 24.2. Compound 5c: 1H
NMR: (200 MHz, d ppm, CDCl3) 8.14–7.20 (m, 14H),
6.71 (d, J = 8.4 Hz, 4H), 6.29 (d, J = 8.4 Hz, 4H), 4.90
(br s, 1H), 4.78 (br s, 1H), 3.15 (q, J = 6.8 Hz, 8H), 0.99
1.70–1.86 (m, 12H); 13C NMR: (50 MHz,
d ppm,
CDCl3) 150.0, 140.1, 134.4, 133.5, 132.2, 129.2,
128.4, 126.4, 125.4, 125.0, 124.6, 123.5, 116.0, 56.1, 50.7,
25.6, 24.2. Crystal data for amine (5c): C42H44N2, MW
576.79, triclinic, space group: P-1, a = 11.2663(8) A,
=
˚
˚
˚
b = 13.1471(9) A, c = 13.8028(9) A, a = 102.9260(10)ꢁ,
3
˚
b = 111.8580(10)ꢁ, c = 108.1940(10)ꢁ V = 1663.3(2) A ,
Z = 2, qc = 1.152 mg mꢀ3, l = 0.066 mmꢀ1, T = 298(2) K.
Of the 19,581 reflections collected, 7789 were unique
[R(int) = 0.0415]. Refinement on all data converged at
R1 = 0.0710, wR2 = 0.1950 (CCDC Deposition Number
293540).
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(t, J = 6.8 Hz, 12H); 13C NMR: (50 MHz,
d ppm,
CDCl3)140.4, 133.6, 132.2, 129.5, 128.4, 126.6, 126.4,
125.4, 125.1, 124.6, 123.7, 112.4, 55.9, 44.6, 12.3.