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PAPER
Table 2 1H NMRa and APCI MS Data of Quinolines 9–18 (continued)
1H NMR d (DMSO-d6), J (Hz)
MS m/z
[M + H]+
9g
0.82 (t, 3J = 6.8, 3 H, CH2CH3), 3.97 (q, 3J = 6.8, 2 H, CH2CH3), 5.01 (s, 2 H, CH2Cl), 7.35 (m, 2 H, Ph), 7.52 (m, 4 326
H, Ph, 5-Qn), 7.66 (t, 3J = 8.4, 1 H, 7-Qn), 7.90 (t, 3J = 8.4, 1 H, 6-Qn), 8.14 (d, 3J = 8.4, 1 H, 8-Qn)
10
2.99 (s, 3 H, CH3), 7.58 (m, 3 H, Ph), 7.77 (m, 1 H, 7-Qn), 7.87 (m, 2 H, Ph), 7.97 (m, 1 H, 6-Qn), 8.12 (d, 3J = 8.4, 245
1 H, 5-Qn), 8.30 (d, 3J = 8.4, 1 H, 8-Qn)
11a
11b
11c
2.95 (s, 3 H, CH3), 7.68 (m, 3 H, 3,4,5-Ph), 7.85 (t, 3J = 8.0, 1 H, 7-Qn), 8.05 (s, 1 H, 3-Qn), 8.30 (m, 4 H, 2,6-Ph, 220
5,6-Qn), 8.48 (m, 1 H, 8-Qn)
2.80 (s, 3 H, CH3), 7.30 (m, 1 H, 4-Th), 7.67 (m, 1 H, 7-Qn), 7.83–7.91 (m, 2 H, 6-Qn, 3-Th), 8.07 (s, 1 H, 3-Qn), 226
8.14 (dd, 3J = 8.4, 4J = 0.9, 1 H, 5-Qn), 8.26–8.30 (m, 2 H, 8-Qn, 5-Th)
2.82 (s, 3 H, CH3), 6.43 (dd, 3J1 = 4.2, 3J2 = 2.1, 1 H, 4-pyr), 7.45 (d, 3J = 2.1, 1 H, 3-pyr), 7.64 (d, 3J = 4.2, 1 H, 5- 209
pyr), 7.72 (t, 3J = 8.4, 1 H, 7-Qn), 7.94 (t, 3J = 8.4, 1 H, 6-Qn), 8.14 (d, 3J = 8.4, 1 H, 5-Qn), 8.24 (s, 1 H, 3-Qn), 8.63
(d, 3J = 8.4, 1 H, 8-Qn), 13.40 (br s, 1 H, NH)
11d
11e
11f
6.82 (dd, 3J = 3.6, 4J = 2.0, 1 H, 4-fur), 7.58–7.70 (m, 6 H), 7.94 (t, 3J = 8.0, 2 H), 8.04 (d, 3J = 6.8, 2 H), 8.18 (m, 1 272
H), 8.65 (m, 1 H, 8-Qn)
7.28 (t, 3J = 8.1, 1 H), 7.42 (t, 3J = 8.1, 1 H), 7.55–7.65 (m, 7 H,), 7.76 (d, 3J = 8.1, 1 H), 7.84 (t, 3J = 8.1, 1 H), 7.92 322
(d, 3J = 8.1, 1 H), 8.10 (m, 2 H), 8.39 (m, 1 H, 8-Qn)
2.69 (s, 3 H, CH3), 6.27 (s, 2 H, CH2), 7.48 (s, 1 H, 5-Qn), 7.52 (s, 1 H, 8-Qn), 7.87 (dd, 3J1 = 8.0, 3J2 = 5.2, 1 H, 5- 265
py), 8.05 (s, 1 H, 3-Qn), 8.82 (dd, 3J = 5.2, 4J = 1.2, 1 H, 6-py), 8.91 (dd, 3J = 8.0, 4J = 1.2, 1 H, 4-py), 9.47 (d,
4J = 1.2, 1 H, 2-py)
11g
1.50 (s, 9 H, CH3), 7.60 (m, 5 H), 7.71 (s, 1 H, 3-Qn), 7.77 (d, 4J = 2.4, 1 H, 5-Qn), 7.85 (dd, 3J = 8.6, 4J = 2.4, 1 H, 297
7-Qn), 8.36 (d, 3J = 8.6, 1 H, 8-Qn)
11h
11i
1.73 (s, 6 H), 2.05 (s, 9 H), 7.52 (m, 6 H), 7.71 (s, 1 H), 7.74 (d, 3J = 9.1, 1 H), 8.09 (m, 1 H)
375
3.04 (t, 3J = 7.85, 2 H), 3.25 (t, 3J = 7.85, 2 H), 7.17 (m, 1 H), 7.37 (t, 3J = 8.8, 2 H), 7.43 (d, 3J = 6.6, 2 H), 7.59 (m, 397
1 H), 7.63 (m, 2 H), 7.69 (m, 2 H), 7.77 (dd, 3J = 9.1, 4J = 2.5, 1 H), 8.08 (d, 3J = 9.1, 1 H)
11j
0.86 (d, 3J = 7.1, 6 H), 3.16 (m, 1 H), 6.98 (s, 1 H), 7.35 (d, 3J = 6.6, 2 H), 7.47 (m, 5 H), 7.55 (m, 3 H), 7.68 (d,
3J = 9.0, 1 H), 8.00 (d, 3J = 9.0, 1 H)
359
230
292
12a
12b
13a
13b
14a
1.38 (t, 3J = 6.9, 3 H, CH2CH3), 2.81 (s, 3 H, CH3), 2.85 (s, 3 H, CH3), 4.50 (q, 3J = 6.9, 2 H, CH2CH3), 7.86 (t,
3J = 8.7, 1 H, 7-Qn), 8.05 (t, 3J = 8.7, 1 H, 6-Qn), 8.36 (d, 3J = 8.7, 1 H, 5-Qn), 8.58 (d, 3J = 8.7, 1 H, 8-Qn)
0.88 (t, 3J = 7.2, 3 H, CH2CH3), 2.68 (s, 3 H, CH3), 4.02 (q, 3J = 7.2, 2 H, CH2CH3), 7.34 (m, 2 H, Ph), 7.54 (m, 5
H, Ph, 5,6-Qn), 7.81 (t, 3J = 8.3, 1 H, 7-Qn), 8.04 (d, 3J = 8.3, 1 H, 8-Qn)
2.74 (s, 3 H, CH3), 3.03 (s, 3 H, CH3), 3.98 (s, 2 H, CH2), 7.82 (t, 3J = 8.4, 1 H, 7-Qn), 7.98 (t, 3J = 8.4, 1 H, 6-Qn), 216
8.34 (d, 3J = 8.4, 1 H, 5-Qn), 8.66 (d, 3J = 8.4, 1 H, 8-Qn)
3.00 (s, 3 H, CH3), 3.71 (s, 2 H, CH2), 7.31 (m, 2 H, Ph), 7.45 (d, 3J = 8.4, 1 H, 5-Qn), 7.64 (m, 3 H, Ph), 7.77 (t,
3J = 8.4, 1 H, 7-Qn), 8.06 (t, 3J = 8.4, 1 H, 6-Qn), 8.49 (d, 3J = 8.4, 1 H, 8-Qn)
278
2.49 (s, 3 H, CH3), 2.96 (s, 3 H, CH3), 3.15 (t, 3J = 6.9, 2 H, CH2), 4.55 (t, 3J = 6.9, 2 H, OCH2), 7.11 (d, 3J = 8.1, 1 276
H, 6-Ar), 7.41 (d, 3J = 8.1, 1 H, 5-Ar), 7.83 (t, 3J = 8.4, 1 H, 7-Qn), 7.89 (s, 1 H, 3-Ar), 7.94 (t, 3J = 8.4, 1 H, 6-Qn),
8.35 (d, 3J = 8.4, 1 H, 5-Qn), 8.76 (d, 3J = 8.4, 1 H, 8-Qn)
14b
14c
1.73 (m, 4 H, CH2CH2CH2CH2CH), 1.89 (m, 2 H, CH2CH2CH2CH2CH), 2.62 (s, 3 H, CH3), 3.00 (m, 2 H,
CH2CH2CH2CH2CH), 3.07 (s, 3 H, OCH3), 3.15 (m, 1 H, CH2CH2CH2CH2CH), 7.44 (t, 3J = 8.4, 1 H, 7-Qn), 7.55
(t, 3J = 8.4, 1 H, 6-Qn), 7.81 (d, 3J = 8.4, 1 H, 5-Qn), 7.94 (d, 3J = 8.4, 1 H, 8-Qn)
270
2.72 (s, 3 H, CH3), 2.94 (m, 2 H, CH2CH2N), 3.55 (m, 2 H, CH2CH2N), 3.72 (s, 2 H, CH2N), 4.56 (m, 2 H, NCH2Ph), 289
7.45 (m, 3 H, Ph), 7.81 (m, 3 H, Ph, 7-Qn), 7.91 (t, 3J = 8.1, 1 H, 6-Qn), 8.29 (d, 3J = 8.1, 1 H, 5-Qn), 8.36 (d, 3J = 8.1,
1 H)
14d
14e
2.17 (qt, 3J = 6.9, 2 H, CH2CH2CH2), 2.89 (t, 3J = 6.9, 2 H, CH2), 3.17 (t, 3J = 6.9, 2 H, CH2), 7.64 (d, 3J = 8.4, 2 H, 246
Ph), 7.40–7.54 (m, 6 H, Ph, 5,6,7-Qn), 7.93 (d, 3J = 8.4, 1 H, 8-Qn)
1.35 (m, 2 H), 1.48 (m, 4 H), 1.95 (m, 2 H), 2.80 (t, 3J = 6.0, 2 H), 3.49 (t, 3J = 6.0, 2 H), 7.32 (d, 3J = 8.4, 1 H, 5- 288
Qn), 7.37 (d, 3J = 8.0, 2 H, Ph), 7.82 (m, 3 H, Ph), 7.86 (t, 3J = 8.4, 1 H, 7-Qn), 8.05 (t, 3J = 8.4, 1 H, 6-Qn), 8.51 (d,
3J = 8.4, 1 H, 8-Qn)
Synthesis 2007, No. 8, 1214–1224 © Thieme Stuttgart · New York