6482
N. Lebouvier et al. / Tetrahedron Letters 47 (2006) 6479–6483
Table 4. Experimental data of synthesized compounds 23a–d and 24a–e
Compd R1
2,4-DiF
R2
F
Yield (%) Mp (°C)
Molecular formula
and weight
1H NMR (DMSO-d6)
23a
23b
23c
23d
24a
25
18
90
80
73
125–126
(Hexane)
C
19H15F3N4O
4.54 (d, 1H, J = 14.8 Hz), 4.58 (d, 1H, J = 14.2 Hz), 4.69
(d, 1H, J = 14.8 Hz), 4.88 (d, 1H, J = 14.2 Hz), 6.30 (s,
1H), 6.37 (d, 1H, J = 3.1 Hz), 6.85 (ddd, 1H, J = 8.6 Hz,
J = J = 2.4 Hz), 6.92 (ddd, 1H, J = J = 9.2 Hz,
J = 2.5 Hz), 7.19 (d, 1H, J = 3.1 Hz), 7.27 (dd, 1H,
J = 7.0 Hz, J = 2.5 Hz), 7.16–7.27 (m, 2H), 7.36 (dd, 1H,
J = 9.2 Hz, J = 4.3 Hz), 7.82 (s, 1H), 8.34 (s, 1H)
4.53 (d, 1H, J = 15.0 Hz), 4.59 (d, 1H, J = 14.4 Hz), 4.70
(d, 1H, J = 15.0 Hz), 4.88 (d, 1H, J = 14.4 Hz), 6.30 (s,
1H), 6.38 (d, 1H, J = 3.1 Hz), 6.85 (ddd, 1H, J = 8.9 Hz,
J = J = 2.4 Hz), 7.14–7.25 (m, 2H), 7.08 (dd, 1H,
J = 8.5 Hz, J = 1.8 Hz), 7.28 (d, 1H, J = 3.1 Hz), 7.39 (d,
1H, J = 8.5 Hz), 7.52 (d, 1H, J = 1.8 Hz), 7.83 (s, 1H),
8.34 (s, 1H)
4.54 (d, 1H, J = 14.8 Hz), 4.59 (d, 1H, J = 14.2 Hz), 4.70
(d, 1H, J = 14.8 Hz), 4.88 (d, 1H, J = 14.2 Hz), 6.31 (s,
1H), 6.38 (d, 1H, J = 3.1 Hz), 6.85 (ddd, 1H, J = 8.2 Hz,
J = J = 2.4 Hz), 7.15–7.27 (m, 2H), 7.18 (dd, 1H,
J = 8.9 Hz, J = 1.5 Hz), 7.27 (d, 1H, J = 3.1 Hz), 7.36 (d,
1H, J = 8.9 Hz), 7.67 (d, 1H, J = 1.5 Hz), 7.83 (s, 1H),
8.34 (s, 1H)
4.60 (d, 1H, J = 15.0 Hz), 4.63 (d, 1H, J = 14.5 Hz), 4.79
(d, 1H, J = 15.0 Hz), 4.90 (d, 1H, J = 14.5 Hz), 6.33 (s,
1H), 6.54 (d, 1H, J = 3.4 Hz), 6.84 (ddd, 1H, J = 8.2 Hz,
J = J = 2.5 Hz), 7.12–7.26 (m, 2H), 7.38 (d, 1H,
J = 3.4 Hz), 7.45 (dd, 1H, J = 8.6 Hz, J = 1.2 Hz), 7.54 (d,
1H, J = 8.6 Hz), 7.85 (s, 1H), 8.03 (d, 1H, J = 1.2 Hz),
8.35 (s, 1H)
4.60 (d, 1H, J = 14.4 Hz), 4.74 (d, 1H, J = 15.0 Hz), 4.91
(d, 1H, J = 15.0 Hz), 5.29 (d, 1H, J = 14.4 Hz), 6.38 (s,
1H), 6.38 (d, 1H, J = 3.7 Hz), 6.97 (ddd, 1H,
(372.34)
2,4-DiF Cl
2,4-DiF Br
2,4-DiF CN
96–97
(Hexane)
C
19H15ClF2N4O
(388.80)
132–133
(Hexane)
C
19H15BrF2N4O
(433.25)
115–116
(Hexane)
C
20H15F2N5O
(379.36)
2,4-DiCl
F
145–147
C
19H15Cl2FN4O
(Hexane)
(405.25)
J = J = 9.2 Hz, J = 2.4 Hz), 7.20 (d, 1H, J = 3.7 Hz), 7.22
(dd, 1H, J = 8.9 Hz, J = 2.1 Hz), 7.27 (dd, 1H, J = 4.6 Hz,
J = 2.4 Hz), 7.36 (d, 1H, J = 8.9 Hz), 7.49 (dd, 1H,
J = 9.2 Hz, J = 4.3 Hz), 7.62 (d, 1H, J = 2.1 Hz), 7.80 (s,
1H), 8.33 (s, 1H)
24b
24c
24d
24e
2,4-DiCl Cl
2,4-DiCl Br
2,4-DiCl CN
47
45
46
157–158
(Hexane)
C
19H15Cl3N4O
4.61 (d, 1H, J = 14.7 Hz), 4.75 (d, 1H, J = 15.0 Hz), 4.92
(d, 1H, J = 15.0 Hz), 5.29 (d, 1H, J = 14.7 Hz), 6.38 (s,
1H), 6.39 (d, 1H, J = 3.7 Hz), 7.12 (dd, 1H, J = 8.9 Hz,
J = 2.0 Hz), 7.22 (dd, 1H, J = 8.5 Hz, J = 2.1 Hz), 7.23 (d,
1H, J = 3.7 Hz), 7.33 (d, 1H, J = 8.5 Hz), 7.52 (d, 1H,
J = 8.9 Hz), 7.54 (d, 1H, J = 2.0 Hz), 7.62 (d, 1H,
J = 2.1 Hz), 7.81 (s, 1H), 8.33 (s, 1H)
4.62 (d, 1H, J = 14.3 Hz), 4.74 (d, 1H, J = 15.0 Hz), 4.92
(d, 1H, J = 15.0 Hz), 5.28 (d, 1H, J = 14.3 Hz), 6.38 (s,
1H), 6.38 (d, 1H, J = 3.4 Hz), 7.21 (dd, 1H, J = 8.9 Hz,
J = 2.1 Hz), 7.23 (d, 1H, J = 3.4 Hz), 7.24 (dd, 1H,
J = 8.9 Hz, J = 1.8 Hz), 7.35 (d, 1H, J = 8.9 Hz), 7.48 (d,
1H, J = 8.9 Hz), 7.62 (d, 1H, J = 1.8 Hz), 7.68 (d, 1H,
J = 2.1 Hz), 7.80 (s, 1H), 8.32 (s, 1H)
4.67 (d, 1H, J = 14.7 Hz), 4.78 (d, 1H, J = 15.3 Hz), 5.01
(d, 1H, J = 15.3 Hz), 5.29 (d, 1H, J = 14.7 Hz), 6.42 (s,
1H), 6.55 (d, 1H, J = 2.8 Hz), 7.20 (dd, 1H, J = 7.3 Hz,
J = 2.1 Hz), 7.31 (d, 1H, J = 7.3 Hz), 7.33 (d, 1H,
J = 2.8 Hz), 7.48 (dd, 1H, J = 7.6 Hz, J = 1.2 Hz), 7.63 (d,
1H, J = 2.1 Hz), 7.65 (d, 1H, J = 7.6 Hz), 7.84 (s, 1H),
8.05 (d, 1H, J = 1.2 Hz), 8.35 (s, 1H)
3.82 (s, 3H), 4.59 (d, 1H, J = 14.7 Hz), 4.80 (d, 1H,
J = 15.0 Hz), 4.90 (d, 1H, J = 15.0 Hz), 5.32 (d, 1H,
J = 14.7 Hz), 6.40 (s, 1H), 6.44 (d, 1H, J = 3.1 Hz), 7.03
(d, 2H, J = 8.6 Hz), 7.24 (dd, 1H, J = 8.9 Hz, J = 3.4 Hz),
7.40 (d, 1H, J = 8.9 Hz), 7.42 (d, 1H, J = 3.1 Hz), 7.44–
7.53 (m, 1H), 7.57 (d, 1H, J = 8.2 Hz), 7.61 (d, 2H,
J = 8.6 Hz), 7.64 (d, 1H, J = 3.4 Hz), 7.71 (s, 1H), 7.80 (s,
1H), 8.34 (s, 1H)
(421.71)
167–168
(Hexane)
C
19H15BrCl2N4O
(466.16)
165–167
(Hexane)
C
20H15BrCl2N5O
(412.27)
2,4-DiCl 4-OMePh 10
128–130
(Hexane)
C
26H22Cl2N4O2
(493.38)