March 1998
SYNTHESIS
273
Table 1. Alkynes 5
Product Yield
mp
(°C)
1H NMR (250 MHz, CDCl3)
d, J (Hz)
13C NMR (250 MHz, CDCl3)
d, J (Hz)
MS-FAB
(%)
m/z M+
5a8
95
89
57–59
oil
7.3–7.4 (m, 3 H, Ar–H), 7.42–7.6
(m, 2 H, Ar–H)
90.04 (ºC), 123.91 (Ar–C), 128.93
178
192
(Ar–C), 129.00 (Ar–C), 132.28 (Ar–C)
5b26
2.68 (s, 3 H, Ar–CH3), 7.23–7.4
(m, 3 H, Ar–H), 7.42–7.55 (m,
3 H, Ar–H), 7.61–7.73 (m, 3 H,
Ar–H)
21.3 (CH3), 89.04 (ºC), 94.05 (ºC),
123.63 (Ar–C), 124.15 (Ar–C), 126.21
(Ar–C), 128.76 (Ar–C), 128.94 (Ar–
C), 130.07 (Ar–C), 132.1 (Ar–C),
132.43 (Ar–C), 140.71 (Ar–C)
86.83 (ºC), 95.17 (ºC), 123.49 (Ar–
C), 123.79 (Ar–C), 127.07 (Ar–C),
128.80 (Ar–C), 129.0 (Ar–C), 129.27
(Ar–C), 129.88 (Ar–C), 131.88 (Ar–
C), 132.34 (Ar–C), 133.82 (Ar–C),
136.5 (Ar–C)
5c27
92
oil
7.2–7.33 (m, 3 H, Ar–H), 7.35–
7.5 (m, 3 H, Ar–H), 7.56–7.65
(m, 3 H, Ar–H)
212 + 214
5d28
75
91
oil
2.53 (s, 6 H, Ar–CH3), 7.1–7.3
(m, 6 H, Ar–H), 7.45–7.55 (m,
2 H, Ar–H)
21.58 (CH3), 92.98 (ºC), 123.97 (Ar–
C), 126.23 (Ar–C), 128.83 (Ar–C),
130.1 (Ar–C), 132.49 (Ar–C), 140.54
(Ar–C),
206
192
5e29
29–30
2.5 (s, 3 H, Ar–CH3), 7.2–7.6
(m, 7 H, Ar–H), 7.65–7.8 (m,
2 H, Ar–H)
21.74 (CH3), 89.73 (ºC), 90.30 (ºC),
123.72 (Ar–C), 124.03 (Ar–C), 128.72
(Ar–C), 128.82 (Ar–C), 128.90 (Ar–
C), 129.30 (Ar–C), 132.17 (Ar–C),
132.77 (Ar–C), 138.50 (Ar–C)
22.12 (CH3), 88.38 (ºC), 90.22 (ºC),
120.82 (Ar–C), 121.50 (Ar–C), 128.69
(Ar–C), 128.94 (Ar–C), 129.09 (Ar–
C), 129.74 (Ar–C), 132.14 (Ar–C),
138.98 (Ar–C)
5f30
93
88
59–61
52–54
2.43 (s, 3 H, Ar–CH3), 7,13–7.3
(m, 2 H, Ar–H), 7.32–7.7 (m,
7 H, Ar–H)
192
208
5g31
3.64 (s, 3 H, CH3O), 6.65–6.75
(m, 3 H, Ar–H), 7.1–7.25 (m,
3 H, Ar–H), 7.29–7.4 (m, 3 H,
Ar–H)
55.66 (OCH3), 88.65 (ºC), 90.01
(ºC), 114.51 (Ar–C), 115.84 (Ar–C),
124.12 (Ar–C), 127.82 (Ar–C), 128.46
(Ar–C), 128.85 (Ar–C), 131.94 (Ar–
C), 133.56 (Ar–C), 160.11 (Ar–OCH3)
5h
97
86
110–112
150–152
3.85 (s, 3 H, CH3O), 6.8–6.95
(m, 2 H, Ar–H), 7.4–7.51 (m,
2 H, Ar–H), 7.59 (s, 4 H, Ar–H)
56.01 (OCH3), 87.53 (ºC), 92.60
(ºC), 114.8 (Ar–C), 125.9 (Ar–C),
127.4–131.9 (3 ´ Ar–C), 132.3 (Ar–C),
133.9 (Ar–C), 160.7 (Ar–C)
276
238
5i32
3.85 (s, 6 H, MeO), 6.82–6.92
(m, 4 H, Ar–H), 7.41–7.5 (m,
4 H, Ar–H)
55.81 (OCH3), 88.59 (ºC), 114.57
(Ar–C), 116.30 (Ar–C), 133.49 (Ar–
C), 160,0 (Ar–C)
5j33
86
89
174–176
94–96
7.31–7.41 (m, 4 H, Ar–H), 7.43–
7.54 (m, 4 H, Ar–H)
6.9–7.15 (m, 4 H, Ar–H), 7.43–
7.6 (m, 4 H, Ar–H)
89.93 (ºC), 122.09 (Ar–C), 129.41
(Ar–C), 133.45 (Ar–C), 135.16 (Ar–C)
88.65 (ºC), 116.33 (d,2JCF = 22, Ar–
C), 119.9 (Ar–C), 134.12 (d,3JCF = 8,
Ar–C), 162.5 (d,1JCF = 250, Ar–C)
40.95 (CH3), 88.76 (ºC), 111.78 (Ar–
C), 112.60 (Ar–C), 133.03 (Ar–C),
150.35 (Ar–C)
246 + 248
214
5k33,34
5l35
87
95
240–243
66–70
3.02 [s, 12 H, N(CH3)2], 6.65
(d, 4 H, J = 8.5, Ar–H), 7.4 (d,
4 H, J = 8.5, Ar–H)
264
190
5m28, 36
6.99 (dd, 2 H, J = 5.1, 3.7,
C4H3S), 7.26 (d, 2 H, J = 3.7,
C4H3S), 7.25–7.28 (m, 2 H,
C4H3S)
86.9 (ºC), 127.8 (C4H3S), 128.3
(C4H3S), 128.3 (C4H3S), 130.4–130.5
(C4H3S), 132.8 (C4H23S)
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