FEATURE ARTICLE
Mesomeric Betaines and N-Heterocyclic Carbenes of Indazole
1889
Table 1 Indazole Derivatives 4, 10, 12, 14–16, 18–28, 30–37 Prepared (continued)
Product
Mp (°C)
n.d.c
1H NMR (DMSO-d6)
d, J (Hz)
13C NMR (DMSO-d6)
d, J (Hz)
ESI-
MSa
m/z
14
9.53 (s, 1 H), 9.21 (d, J = 2.1 Hz, 1 H), 8.60 (dd, J = 9.6
Hz, 2.1, 1 H), 8.25 (d, J = 9.6 Hz, 1 H), 4.47 (s, 3 H), 4.43
(s, 3 H)
n.d.c
192.1
15a
15b
16a
16b
18a
194b,d
167
8.09 (d, J = 9.6 Hz, 1 H), 7.78 (dd, J = 9.6 Hz, 1.8, 1 H),
7.21 (s, 1 H), 4.57 (s, 3 H), 4.38 (s, 3 H), 3.06 (s, 6 H)
159.4, 148.3, 134.4, 127.7, 124.5,
121.4, 112.4, 112.2, 36.6, 34.1
234.1
191.1
234.1
197.1
190.1
8.31 (m, 1 H), 8.16 (m, 1 H), 7.93 (m, 1 H), 7.64 (m, 1 H), 158.7, 139.2, 133.0, 131.9, 126.8,
4.63 (s, 3 H, CH3), 4.40 (s, 3 H, CH3)
123.2, 119.5, 111.6, 36.8, 34.0
135b
7.76 (d, J = 9.7 Hz, 1 H), 7.54 (d, J = 9.7 Hz, 1 H), 7.40
(s, 1 H), 4.61 (s, 3 H), 4.16 (s, 3 H), 2.96 (s, 6 H)
158.4, 147.7, 134.0, 133.8, 123.5,
120.8, 110.7, 101.4, 34.6, 32.6
148–151
186–188
8.33 (m, 1 H), 8.02 (m, 1 H), 7.92 (m, 1 H), 7.62 (m, 1 H), 158.7, 139.1, 132.9, 132.8, 126.4,
4.63 (s, 3 H, CH3), 4.36 (s, 3 H, CH3)
123.4, 119.4, 111.3, 36.4, 33.7
8.86 (s, 1 H), 7.84 (d, J = 9.5 Hz, 1 H), 7.63 (dd, J = 9.5
147.9, 134.6, 130.0, 124.1, 120.2,
Hz, 2.0, 1 H), 6.96 (d, J = 2.0 Hz, 1 H), 4.32 (s, 3 H), 4.21 111.4, 98.5, 37.3, 33.0
(s, 3 H), 2.97 (s, 6 H)
19a
19b
20
136–137
118
7.19 (m, 3 H), 3.94 (s, 3 H), 3.48 (s, 3 H), 2.99 (s, 6 H)
147.88, 138.94, 128.25, 121.02, 110.80, 222.1
109.18, 106.02, 41.60, 36.43, 32.45
8.05 (m, 1 H), 7.56 (m, 1 H), 7.27–7.15 (m, 2 H), 3.97
(s, 3 H, CH3), 3.62 (s, 3 H, CH3)
171.0, 144.2, 132.0, 126.7, 125.2,
122.5, 109.7, 35.3, 32.3
179.1
208–211b
8.71 (m, 1 H), 7.94 (m, 1 H), 7.80 (m, 1 H), 7.68 (d, J = 1.9 159.0, 154.3, 139.1, 132.9, 132.1,
Hz, 2 H), 7.46 (m, 1 H), 6.90 (t, J = 1.9 Hz, 1 H), 4.77
(s, 3 H, CH3), 4.24 (s, 3 H, CH3)
334.2
126.0, 124.3, 122.4, 119.0, 118.7,
110.4, 110.4, 35.5, 32.8
21
212–214b
8.93 (d, J = 8.5 Hz, 1 H), 8.32 (d, J = 8.8 Hz, 1 H), 7.94
(d, J = 8.70 Hz, 1 H), 7.80 (dd, J = 7.4 Hz, 7.2, 1 H), 7.47 128.4, 127.9, 126.3, 126.2, 125.7,
158.0, 147.4, 141.9, 139.1, 132.1,
334.2
(dd, J = 7.4 Hz, 7.6, 1 H), 7.39 (d, J = 2.4 Hz, 1 H), 7.17
(dd, J = 8.8 Hz, 2.4, 1 H), 4.85 (s, 3 H, CH3), 4.25
(s, 3 H, CH3)
124.2, 122.8, 119.3, 110.3, 35.5, 32.8
22
23
24
26
27
28
30
175–178b
238b
8.66 (m, 1 H), 7.96 (m, 1 H), 7.83 (m, 1 H), 7.82 (m, 2 H), 201.3, 163.4, 160.4, 146.4, 144.3,
7.69 (m, 2 H), 7.48 (m, 1 H), 4.76 (s, 3 H, CH3), 4.26 (s, 3 137.4, 134.5, 134.1, 130.8, 129.6,
308.1
334.2
334.2
304.2
350.2
350.2
266.1
H, CH3), 2.49 (s, 3 H, CH3)
128.5, 124.1, 115.7, 40.8, 38.1, 31.5
8.12 (m, 1 H), 8.02 (m, 1 H), 7.93 (m, 1 H), 7.81 (d, J = 1.8 155.8, 140.0, 139.8, 135.0, 134.3,
Hz, 2 H), 7.61 (m, 1 H), 7.46 (t, J = 1.8 Hz, 1 H), 4.43
(s, 3 H, CH3), 4.33 (s, 3 H, CH3)
127.0, 125.5, 12.8, 119.9, 118.1, 112.4,
111.9, 37.5, 34.4
193b
8.26 (m, 1 H), 8.16 (m, 1 H), 7.20–8.04 (m, 3 H), 7.55–
7.75 (m, 2 H), 4.53 (s, 3 H, CH3), 4.43 (s, 3 H, CH3)
155.3, 139.1, 134.5, 133.4, 132.2,
132.1, 130.0, 129.3, 129.3, 128.0,
126.2, 122.1, 117.5, 111.5, 36.9, 33.9
168–170b
180–183
172–174b
200–202b
8.21 (m, 1 H), 7.91 (m, 1 H), 7.81 (m, 1 H), 7.43 (m, 1 H), 169.3, 152.4, 145.7, 139.2, 132.3,
7.23–7.32 (m, 4 H), 6.96 (m, 1 H), 4.40 (s, 3 H, CH3), 4.23 127.9, 123.9, 123.7, 122.2, 121.9,
(s, 3 H, CH3)
117.2, 110.3, 34.8, 32.7
8.24 (m, 1 H), 7.92 (m, 1 H), 7.81 (m, 1 H), 7.44 (m, 1 H), 172.7, 155.3, 145.2, 139.2, 133.3,
7.29 (m, 1 H), 7.14 (m, 1 H), 4.40 (s, 3 H, CH3), 4.24
(s, 3 H, CH3)
132.5, 124.0, 123.9, 121.0, 121.0,
117.2, 110.5, 35.2, 32.9
8.25 (m, 1 H), 7.93 (m, 1 H), 7.82 (m, 1 H), 7.52 (m, 1 H), 172.6, 149.3, 145.2, 139.2, 132.4,
7.46 (m, 1 H), 7.32 (m, 2 H), 4.48 (s, 3 H, CH3), 4.25
(s, 3 H, CH3)
128.3, 126.9, 126.0, 125.7, 124.5,
123.9, 123.8, 117.2, 110.4, 35.1, 32.8
11.39 (s, 1 H), 8.16 (m, 2 H), 7.98 (m, 1 H), 7.80 (m, 2 H), 154.6, 139.1, 137.4, 135.2, 133.4,
7.65 (m, 1 H), 7.47 (m, 2 H), 7.26 (m, 1 H), 4.49 (s, 3 H,
CH3), 4.42 (s, 3 H, CH3)
129.0, 125.9, 125.4, 122.5, 120.8,
117.3, 111.4, 36.9, 33.8
Synthesis 2006, No. 11, 1882–1894 © Thieme Stuttgart · New York