3804
N. A. Tolmachova et al.
PAPER
Table 2 Selected Physical and Spectral Data of Synthesized Products (continued)
Compd
(solvent) (%)
Yield 19F NMR [d (ppm)]
1H NMR [d (ppm)]
13C NMR [d (ppm)]
22f
(CDCl3)
83
–65.53 (s)
5.23 (1 H, d, J3,4 = 10.4 Hz, H-3), 6.86 (1 H, d,
J4,3 = 10.4 Hz, H-4), 7.31 (2 H, m, H-11, H-12),
78.2, 88.9 (t, J = 26.1 Hz), 90.6, 105.2,
113.6, 115.3, 122.9, 124.0, 128.1, 128.2,
7.44 (3 H, m, H-22, H-24, H-26), 7.53 (2 H, m, H- 129.7, 129.8, 129.9 (t, J = 309.0 Hz),
25, H-23), 7.07 (1 H, m, H-13), 7.85 (1 H, m, H- 138.6, 149.5, 180.7
10), 8.00 (1 H, s, OH), 13.17 (1 H, br s, NH)
22i
(CDCl3)
43
–80.80 (3 F, t, J = 8.2
Hz), –119.00 (2 F, br
4.95 (1 H, d, J3,4 = 10.1 Hz, H-3), 6.78 (1 H, d,
J4,3 = 10.1 Hz, H-4), 7.29 (2 H, m, H-11, H-12),
88.0, 88.8, 90.6, 101.7, 113.2, 115.4, 123.3,
124.7, 128.2, 128.6, 129.7, 130.0, 130.4,
m), –123.96 (2 F, br s) 7.47 (5 H, s, H-22, H-23, H-24, H-25, H-26), 7.70 131.9, 140.5, 148.2, 174.8 (t, J = 27.9 Hz)a
(1 H, m, H-13), 7.84 (1 H, m, H-10), 9.06 (1 H, s,
OH), 13.21 (1 H, br s, NH)
23a
(CDCl3)
85
94
56
–65.24 (s)
–65.70 (s)
–65.86 (s)
7.57 (1 H, m, H-6), 7.69 (2 H, m, H-8, H-7), 8.04 106.4, 112.0, 114.6, 115.1, 120.3 (q, J =
(1 H, d, J11,12 = 7.8 Hz, H-11), 8.09 (1 H, d, 271.8 Hz), 121.0, 124.2, 127.4, 127.8, 129.7
J12,11 = 7.8 Hz, H-12), 8.33 (1 H, d, J9,8 = 7.3 Hz, (q, J = 36.2 Hz), 136.6, 144.6, 146.4
H-9)
23b
(CDCl3)
7.47 (4 H, m, H-Ar), 7.59 (3 H, m, H-Ar), 7.94
110.0 (q, J = 6.6 Hz), 114.2 (q, J = 6.6 Hz),
(2 H, m, H-6, H-11), 8.00 (1 H, d, J12,11 = 8.1 Hz, 120.5 (q, J = 273.2 Hz), 123.3, 126.4, 126.5,
H-12), 8.18 (1 H, d, J9,8 = 8.6 Hz, H-9)
127.4, 128.6 (q, J = 36.8 Hz), 128.6, 133.0,
134.2, 136.0, 145.0 146.1 192.4
23c
(CDCl3)
4.01 (3 H, s, CH3), 7.35 (1 H, d, J11,12 = 7.8 Hz, H- 53.0, 106.4, 111.9, 114.6, 115.1, 120.0 (q,
11), 7.51 (1 H, m, H-8), 7.62 (1 H, m, H-7), 7.95 J = 271.8 Hz), 124.3, 127.4, 127.8, 129.7 (q,
(1 H, d, J12,11 = 7.8 Hz, H-12), 8.44 (1 H, d,
J = 36.2 Hz), 137.0, 144.0, 146.5, 160.5
J6,7 = 7.3 Hz, H-6), 9.43 (1 H, d, J9,8 = 7.3 Hz, H-
9)
23d
(CDCl3)
76
–65.32 (s)
4.86 (2 H, d, J = 6.1 Hz, CH2), 7.34 (3 H, m, H-
Ar), 7.49 (4 H, m, H-Ar), 7.62 (1 H, m, H-8), 7.96 Hz), 120.3, 120.5 (q, J = 272.9 Hz), 124.8,
43.9, 111.3 (q, J = 7.8 Hz), 114.5 (q, J = 7.8
(1 H, d, J12,11 = 7.4 Hz, H-12), 8.16 (1 H, br d,
J6,7 = 8.8 Hz, H-6), 8.57 (1 H, d, J11,12 = 7.4 Hz,
H-11), 11.13 (1 H, br s, NH)
126.8, 127.4, 127.5, 128.7 (q, J = 35.3 Hz),
129.1, 130.4, 138.3, 143.5, 146.6, 162.1
23e
(CDCl3)
79
83
73
95
–51.64 (s)
–53.56 (s)
7.16 (1 H, m, H-9), 7.53 (1 H, m, H-8), 7.65 (1 H, 99.4 (t, J = 3.5 Hz), 105.3 (t, J = 5.4 Hz),
m, H-7), 7.99 (1 H, d, J12,11 = 7.7 Hz, H-12), 8.07 111.1, 111.7, 121.2, 123.1 (t, J = 28.3 Hz),
(1 H, d, J11,12 = 7.7 Hz, H-11), 8.78 (1 H, d,
J6,7 = 6.1 Hz, H-6)
123.9, 127.9, 128.5, 129.5, 141.4 (t, J = 28.3
Hz), 144.5, 145.3
23f
(CDCl3)
7.47 (4 H, m, H-Ar), 7.59 (3 H, m, H-Ar), 7.65
109.2 (t, J = 8.0 Hz), 115.9 (t, J = 7.6 Hz),
(1 H, m, H-Ar), 7.94 (2 H, m, H-Ar), 8.00 (1 H, d, 121.5 (t, J = 288.2 Hz), 123.1, 126.3, 126.6,
J12,11 = 7.8 Hz, H-12), 8.18 (1 H, d, J11,12 = 7.8 Hz, 127.5, 128.6, 130.4, 132.5, 133.9 (t, J = 33.7
H-11)
Hz), 134.2, 136.0, 145.1, 146.3, 192.4
23i
(CDCl3)
–80.13 (3 F, t, J = 8.8
Hz), –107.44 (2 F, q,
J = 8.8 Hz), –123.33
(2 F, s)
7.44 (4 H, m, H-Ar), 7.59 (3 H, m, H-Ar), 7.94
113.7 (t, J = 9.7 Hz), 115.1 (t, J = 11.5 Hz),
(2 H, m, H-6, H-11), 8.00 (1 H, d, J12,11 = 8.1 Hz, 121.2, 123.2, 125.8, 126.3, 128.1 (t, J = 32.2
H-12), 8.09 (1 H, d, J9,8 = 8.6 Hz, H-9)
Hz), 128.2, 128.7, 133.6, 132.5, 134.2, 135.9,
145.0, 146.5, 192.3a
26b
(DMSO-
–66.88 (3 F, s),
–80.58 (3 F, s)
3.57 (3 H, s, CH3), 7.15 (2 H, m, H-11, H-12),
52.0, 89.0, 89.3 (q, J = 35.0 Hz), 97.4, 116.8
7.45 (1 H, d, J10,11 = 7.8 Hz, H-10), 7.73 (1 H, d, (q, J = 2.3 Hz), 118.3 (q, J = 290.1 Hz), 125.6
d6)
J13,12 = 7.5 Hz, H-13), 9.04 (1 H, s, H-4), 9.05
(1 H, s, NH), 12.94 (1 H, s, OH)
(q, J = 296.7 Hz), 125.7, 126.5, 130.4, 131.7,
144.6 (q, J = 2.4 Hz), 146.7, 164.9, 176.4 (q,
J = 33.2 Hz)
27
(DMSO-
d6)
84
56
–66.02 (s)
–70.91 (s)
7.52 (6 H, m, H-7, H-8, H-12, H-23, H-24, H-25), 109.4 (q, J = 6.1 Hz), 114.0 (q, J = 6.1 Hz),
8.09 (2 H, m, H-6, H-11), 8.39 (3 H, m, H-9, H-
22, H-26)
119.9 (q, J = 272.6 Hz), 121.4, 123.6, 126.6,
127.2, 128.6, 129.1, 129.5, 131.0 (q, J = 36.1
Hz), 133.2, 133.9, 138.7, 144.7
29
(DMSO-
d6)
3.71 (3 H, s, CH3), 5.70 (1 H, d, J9,8 = 13.0 Hz, H- 32.1, 67.5, 98.3, 111.0, 112,1, 118.0, 118.5
9), 7.13 (2 H, m, H-12, H-8), 7.23 (1 H, m, H-7), (q, J = 296.3 Hz), 124.3, 125.1, 130.8, 133.6,
7.42 (1 H, s, NH), 8.08 (1 H, d, J6,7 = 13.6 Hz, H- 149.5, 149.9, 174.1 (q, J = 32.4 Hz)
6)
Synthesis 2007, No. 24, 3797–3806 © Thieme Stuttgart · New York