PAPER
Synthesis and Reactions of 2- and 4-Phosphonatoquinolines and Related Compounds
2079
Table 5 Spectroscopic Data of Compounds 26–34
1
13
Prod- IR n
H NMR (CDCl /TMS)
C NMR (CDCl /TMS)
MS (70 eV)
m/z (%)
3
3
-
1 a
uct
(cm )
d, (ppm), J (Hz)
d, (ppm), J (Hz)
26a
3052,
0.96 (t, 3 H, J = 7.4, CH ), 1.46 (m, 2 H, CH ), 1.82 13.98 (1 C, CH ), 22.97 (1 C, CH ), 31.93 (1 C, CH ), DIE: 185
3 2 3 2 2
+
2
2
2
957,
928,
864
(m, 2 H, CH ), 3.26 (t, 2 H, J = 7.8, CCH ), 7.44 (d, 35.17 (1 C, CCH ),118.98 (1 C, C-4), 125.24 (1 C, C- (M , 10)
2
2
2
1 H, J = 5.7, H-4), 7.55 (t, 1 H, J = 7.0, H-7), 7.58 (t, 8), 126.84 (1 C, C-7), 127.25 (1 C, C-5), 126.78 (1 C,
1 H, J = 7.0, H-6), 7.74 (d, 1 H, J = 8.1, H-5), 8.11 (d, C-8a), 129.59 (1 C, C-6), 136.18 (1 C, C-4a), 141.80
1
H, J = 8.3, H-8), 8.39 (d, 1 H, J = 5.7, H-3)
(1 C, C-3), 162.30 (1 C, C-1)
2
2
6b
6c
3087,
7.51 (m, 4 H, H-7, o, p-Ph), 7.63 (d, 1 H, J = 5.6,
119.38 (1 C, C-4), 126.69 (1 C, C-8a), 126.98 (1 C, EI: 204
+
3
2
2
055,
956,
853
H-4), 7.67 (m, 3 H, H-6, m-Ph), 7.86 (d, 1 H, J = 8.2, C-5), 127.19 (1 C, C-7), 127.57 (1 C, C-8), 129.86
H-5), 8.09 (d, 1 H, J = 8.5, H-8), 8.59 (d, 1 H, J = 5.6, (1 C, C-6), 136.83 (1 C, C-4a), 139.55 (1 C, i-Ph),
H-3) 142.19 (1 C, C-3), 160.72 (1 C, C-1)
0.94 (t, 3 H, J = 7.4, CH ), 1.42 (q, 2 H, J = 7.6, CH ), 13.93 (1 C, CH ), 22.62 (1 C, CH ), 32.15 (1 C, CH ), DIE: 186
(M , 100)
3059,
3
2
3
2
2
+
2
2
2
956,
926,
863
1.76 (m, 2 H, CH ), 2.96 (t, 2 H, J = 7.9, C-CH ), 7.27 38.97 (1 C, CH ), 121.29 (1 C, C-3), 125.57 (1 C,
(M , 48)
2
2
2
(d, 1 H, J = 8.4, H-3), 7.45 (t, 1 H, J = 7.0, H-6), 7.65 C-8), 126.62 (1 C, C-4a), 127.39 (1 C, C-5), 128.63
(t, 1 H, J = 5.5, H-7), 7.74 (d, 1 H, J = 8.0, H-5), 8.03 (1 C, C-7), 129.27 (1 C, C-6), 136.18 (1 C, C-4),
(
d, 2 H, J = 8.4, H-4, 8)
147.71 (1 C, C-8a), 163.02(1 C, C-2)
2
2
6d
6e
3063,
1.45 ( 9 H, CH ), 7.45 (t, 1 H, J = 7.4, H-6), 7.50 (d, 30.12 (3 C, CH ), 38.10 (1 C, CCH ), 118.20 (1 C, C- DIE: 185
1 H, J = 8.8, H-3), 7.64 (t, 1 H, J = 7.1, H-7), 7.74 (d, 3), 125.58 (1 C, C-8), 126.42 (1 C, C-4a), 127.19 (1 (M , 40)
1 H, J = 8.0, H-5), 8.04 (d, 1 H, J = 8.4, H-8), 8.05 (d, C, C-5), 128.95 (1 C, C-7), 129.36 (1 C, C-6), 135.83
3
3
3
+
2
2
2
959,
927,
857
1 H, J = 8.7, H-4)
(1 C, C-4), 147.39 (1 C, C-8a), 169.24 (1 C, C-2)
3057,
7.45 (d, 1 H, J = 7.2, H-3), 7.51 (t, 3 H, J = 7.0, H-6, 118.96 (1 C, C-3), 126.20 (1 C, C-8), 127.10 (1 C, C- EI: 205
+
3
2
2
2
011,
960,
928,
857
m-Ph), 7.71 (t, 1 H, J = 6.9, H-7), 7.81 (d, 1 H, J = 8.1, 4a), 127.37 (1 C, C-5), 127.49 (1 C, o-Ph), 128.76 (1 (M , 100)
H-5), 7.86 (d, 1 H, J = 8.6, p-Ph), 8.14 (m, 2 H, H-4, C, m-Ph), 129.23 (1 C, C-7), 129.58 (1 C, p-Ph),
8), 8.21 (d, 1 H, J = 8.6, o-Ph)
129.63 (1 C, C-6), 136.71 (1 C, C-4), 139.61 (1 C, i-
Ph), 148.19 (1 C, C-8a), 157.32 (1 C, C-2)
26f
3064,
4.33 (s, 2 H, CH ), 7.16 (d, 1 H, J = 6.4, H-3), 7.0–
45.45 (1 C, CH ), 121.46 (1 C, C-3), 125.92 (1 C, C- EI: 218
2
2
+
3
3
2
2
028,
008,
961,
857
7.22 (m, 5 H, C H ), 7.34 (d, 1 H, J = 8.03, H-5), 7.48 6), 126.41 (2 C, o-Ph), 126.61 (1 C, C-4a), 127.43 (1 (M , 100)
6
5
(t, 1 H, J = 6.9, H-6), 7.69 (t, 1 H, J = 8.45, H-7), 8.01 C, C-5), 128.28 (1 C, C-8), 128.85 (2 C, m-Ph),
(m, 2 H, J = 8.52, H-4), 8.08 (m, 2 H, J = 8.52, H-8) 129.43 (1 C, C-7), 130.56 (1 C, p-Ph), 136.47 (1 C,
C-4), 139.11 (1 C, i-Ph), 147.67 (1 C, C-8a), 147.67
(1 C, C-6)
2
2
2
6g
6h
6i
3066,
0.92 (t, 3 H, J = 7.4, CH ), 1.39 (m, 4 H, CH ), 1.67 13.80 (1 C, CH ), 22.63 (1 C, CH ), 32.05 (1 C, CH ), EI: 186
(m, 2 H, CH ), 2.98 (t, 2 H, J = 7.7, CCH ), 7.15 (d, 31.72 (1 C, CH ), 120.63 (1 C, C-3), 123.48 (1 C, C- (M , 100)
2 2 2
1 H, J = 4.4, H-3), 7.48 (t, 1 H, J = 7.2, H-6), 7.62 (t, 5), 126.06 (1 C, C-6), 127.86 (1 C, C-4a), 128.82 (1
1 H, J = 8.2, H-7), 7.97 (d, 1 H, J = 8.4, H-5), 8.06 (d, C, C-7), 130.07 (1 C, C-8), 148.21 (1 C, C-4), 148.61
3
2
3
2
2
+
2
2
2
2
960,
929,
871,
734
1H, J = 8.4, H-8), 8.74 (d, 1H, J = 4.4, H-2)
7.30 (d, 1 H, J = 4.4, H-3), 7.36 (dd, 1 H, J = 8.2, J = 121.0 (1 C, C-5), 121.30 (1 C, C-3), 125.82 (2 C, o- EI: 205 (M,
4.3, H-5), 7.5 (m, 2 H, Ph-H), 7.69 (t, 1 H, J = 7.1, Ph), 126.67 (1 C, C-4a), 127.73 (1 C, p-Ph), 129.25 100)
H-7), 7.78 (d, 1 H, J = 8.23, Ph-H), 7.89 (d, 2 H, J = (1 C, C-7), 129.47 (2 C, m-Ph), 129.73 (1 C, C-8),
(1 C, C-8a), 152.31 (1 C, C-2)
3061,
3
3
2
2
033,
002,
931,
858
8.14, Ph-H) 8.11 (t, 1 H, J = 9.1, H-6), 8.16 (d, 1H,
J = 8.4, H-8), 8.92 (d, 1H, J = 4.3, H-2)
136.03 (1 C, C-6), 148.17 (1 C, C-4), 148.43 (1 C, C-
8a), 149.92 (1 C, C-2)
3061,
0.91 (t, 3 H, J = 7.3, CH ), 1.34 (m, 2 H, CH ), 1.67 13.84 (1 C, CH ), 22.38 (1 C, CH ), 31.96 (1 C, CH ), EI: 134
3 2 3 2 2
+
2
2
2
954,
926,
855
(m, 2 H, CH ), 2.76 (t, 2 H, J = 7.8, CCH ), 7.06 (t, 38.00 (1 C, C-CH ), 120.75 (1 C, C-5), 122.56 (1 C, (M , 6)
2 2 2
1 H, J = 5.8, H-5), 7.11 (d, 1 H, J = 7.8, H-3), 7.55 (t, C-3), 136.15 (1 C, C-4), 149.04 (1 C, C-6), 162.41 (1
1H, J = 7.6, H-4), 8.49 (d, 1 H, J = 4.2, H-6) C, C-2)
1.34 (s, 9 H, CH ), 7.05 (t, 1 H, J = 6.2, H-5), 7.30 (d, 30.15 (3 C, CCH ), 37.35 (1 C, CCH ), 119.07 (1 C, EI: 136
2
3
6k
0a
3061,
3
3
3
+
2
2
926,
854
1 H, J = 8.1, H-3), 7.57 (t, 1 H, J = 7.5, H-4), 8.54 (d, C-5), 120.80 (1 C, C-3), 136.15 (1 C, C-4), 148.53 (1 (M , 6)
1 H, J = 4.7, H-6) C, C-6), 169.25 (1 C, C-2)
3.21 ( 6 H, CH ), 6.87 (d, 1 H, J = 9.1, H-3), 7.16 (t, 38.05 (2 C, CH ), 109.03 (1 C, C-3), 121.60 (1 C, C- EI: 172
1 H, J = 8.1, H-6), 7.50 (t, 1 H, J = 8.5, H-7), 7.70 (d, 6), 122.39 (1 C, C-4a), 126.27 (1 C, C-8), 127.76 (1 (M , 100)
1 H, J = 8.3, H-8), 7.83 (d, 1 H, J = 8.8, H-4), 8.56 (d, C, C-5), 129.38 (1 C, C-7), 137.14 (1 C, C-4), 148.09
3052,
3
3
+
2
2
927,
854
1
H, J = 7.9, H-5)
(1 C, C-8a), 157.63 (1 C, C-2)
3
3
0b
3072,
2.99 ( 6 H, CH ), 6,71 (d, 1 H, J = 5.1, H-3), 7.41 (t, 43.78 (2 C, CH ), 107.18 (1 C, C-3), 122.89 (1 C, C- EI: 172
1 H, J = 7.9, H-7), 7.59 (t, 1 H, J = 7.8, H-6), 7.99 (d, 4a), 124.39 (1 C, C-5), 124.51 (1 C, C-7), 128.75 (1 (M , 100)
1 H, J = 8.8, H-8), 8.02 (d, 1 H, J = 8.5, H-5), 8.62 (d, C, C-6), 129.71 (1 C, C-8), 149.58 (1 C, C-4), 150.36
3
3
+
2
2
2
947,
845,
792
1 H, J = 5.1, H-2)
(1 C, C-2), 155.28 (1 C, C-8a)
0c
3006,
3.02 (6 H, N-CH ), 6.45 (d, 1 H, J = 8.6, H-3), 6.48 38.00 (2 C, CH ), 105.74 (1 C, C-5), 111.33 (1 C, C- EI: 122
3
3
+
2
2
929,
808
(t, 1 H, J = 6.4, H-5), 7.38 (t, 1 H, J = 6.8, H-4),
8.12(d, 1 H, J = 4.9, H-6)
3), 136.99 (1 C, C-4), 147.78 (1 C, C-6), 159.24 (1 C, (M , 100)
C-2)
3
3
0d
2918,
820,
4ab 3056,
030
2.96 (6 H, N-CH ), 6.45 (d, 2 H, J = 5.0, H-3, 5), 8.18 38.98 (1 C, NCH ), 106.45 (2 C, C-3, 5), 149.22 (2 C, EI: 122
3
3
+
2
(d, 2 H, J = 5.0, H-2, 6)
C-2, 6), 154,27 (1 C, C-4)
(M , 100)
7.48 (m, 3 H, m, p-Ph), 7.60 (m, 2 H, o-Ph, H-3), 8.64 126.97 (2 C, C-3, 5), 128.56, 239.09, 129.06 (5 C, Ar- EI: 155
+
3
(d, 2 H, J = 5.4, H-2, 6)
C), 138.11 (1 C, C-Ph), 148.97 (1 C, C-4), 150.20 (2 (M , 100)
C, C-2/6)
a
Film or KBr.
Compound 34b is equivalent to 26h.
b
Synthesis 1999, No. 12, 2071–2081 ISSN 0039-7881 © Thieme Stuttgart · New York