290
Y. Liu et al.
Arch. Pharm. Chem. Life Sci. 2012, 345, 287–293
Table 2. The IR, 1H-NMR data of compounds 7a–f, 12a–f and 20a–f.
Compd.
7a
IR, n=cmꢂ1
1H-NMR (300 MHz, DMSO-d6), d
–
–
3412.1 (yNH), 1675.8 (yC O),
1601.4, 1521.6, 1409.9 (yC C),
–
9.78 (s, 1H, CNHC O), 8.44 (d, J ¼ 5.8 Hz, 2H, pyridinyl-2H,6H), 8.15 (m, 2H,
–
–
phthalazine-5H,8H), 7.93 (m, 2H, phthalazine-6H,7H), 7.54 (d, J ¼ 8.3 Hz, 2H, Ph-2H,6H),
–
818.0, 779.1 (d–
)
CH
7.31 (d, J ¼ 5.6 Hz, 2H, pyridine-3H,5H), 7.13 (d, J ¼ 8.3 Hz, 2H, Ph-3H,5H), 4.62 (s, 2H, CCH2C),
–
–
–
3.46 (s, 4H, (CH CH ) N), 3.26 (s, 2H, NCH C O), 2.83 (s, 4H, CH N(CH ) ), 2.25 (s, 3H, CCH ).
2
2 2
2
2
2 2
3
–
7b
7c
7d
7e
7f
3298.7 (yNH), 1698.7 (yC O),
–
9.96 (s, 1H, CNHC O), 8.44 (d, J ¼ 5.6 Hz, 2H, pyridinyl-2H,6H), 8.27 (d, J ¼ 8.1 Hz, 1H, Ph-3H),
–
–
1590.1, 1529.3 (yC C),
–
8.18 (m, 2H, phthalazine-5H,8H), 7.94 (m, 2H, phthalazine-6H,7H), 7.72 (m, 2H, Ph-4H,5H),
7.34 (m, 3H, pyridinyl-3H,5H þ Ph-6H), 4.63 (s, 2H, CCH2C), 3.47 (s, 4H, (CH2CH2)2N), 3.34
–
766.5 (d–
)
CH
–
–
–
(s, 2H, NCH C O), 2.89 (s, 4H, CH N(CH ) ).
2
2
2 2
–
–
3269.7 (yNH), 1686.5 (yC O),
10.10 (s, 1H, CNHC O), 8.44 (d, J ¼ 5.6 Hz, 2H, pyridinyl-2H,6H), 8.16 (m, 2H,
–
–
1595.6, 1518.1 (yC C), 877.0,
phthalazine-5H,8H), 7.93 (m, 3H, phthalazine-6H,7H þ Ph-2H), 7.58 (d, J ¼ 7.7 Hz, 1H, Ph-6H),
–
–
778.6, 680.2 (d–
)
CH
7.34 (m, 3H, pyridinyl-3H,5H þ Ph-5H), 7.13 (d, J ¼ 7.7 Hz, 1H, Ph-4H), 4.62 (s, 2H, CCH2C),
–
–
–
3.47 (s, 4H, (CH CH ) N), 3.30 (s, 2H, NCH C O), 2.83 (s, 4H, CH N(CH ) ).
2
2 2
2
2
2 2
–
–
3411.8 (yNH), 1688.3 (yC O),
10.10 (s, 1H, CNHC O), 8.44 (d, J ¼ 5.1 Hz, 2H, pyridinyl-2H,6H), 8.15 (m, 2H,
–
–
1602.4, 1512.9, 1411.6 (yC C),
–
phthalazine-5H,8H), 7.91 (m, 2H, phthalazine-6H,7H), 7.82 (d, J ¼ 9.0 Hz, 2H, Ph-2H,6H),
7.32 (d, J ¼ 7.9 Hz, 4H, pyridine-3H,5H þ Ph-3H,5H), 4.62 (s, 2H, CCH2C), 3.47
–
805.4, 778.5 (d–
)
CH
–
–
(s, 4H, (CH CH ) N), 3.30 (s, 2H, NCH C O), 2.83 (s, 4H, CH N(CH ) ).
–
2
2 2
2
2
2 2
–
3263.4 (yNH), 1671.0 (yC O),
9.93 (s, 1H, CNHC O), 8.44 (d, J ¼ 5.6 Hz, 2H, pyridinyl-2H,6H), 8.15 (m, 2H,
–
–
–
1532.6, 1508.8 (yC C), 836.1,
–
phthalazine-5H,8H), 7.92 (m, 2H, phthalazine-6H,7H), 7.71 (m, 2H, Ph-2H,6H), 7.31
(d, J ¼ 5.7 Hz, 2H, pyridine-3H,5H), 7.16 (t, J ¼ 8.8 Hz, 2H, Ph-3H,5H), 4.62 (s, 2H, CCH2C),
–
779.4 (d–
)
CH
–
–
–
3.47 (s, 4H, (CH CH ) N), 3.27 (s, 2H, NCH C O), 2.83 (s, 4H, CH N(CH ) ).
2
2 2
2
2
2 2
–
–
3422.1 (yNH), 1695.5 (yC O),
10.55 (s, 1H, CNHC O), 8.44 (m, 4H, pyridinyl-2H,6H þ phthalazine-5H,8H), 8.15 (m, 2H,
–
–
1601.6, 1532.4 (yC C), 778.3,
Ph-2H,6H), 7.93 (m, 2H, phthalazine-6H,7H), 7.78 (s, 1H, Ph-4H), 7.32 (d, J ¼ 5.8 Hz, 2H,
–
–
–
Ph-3H,5H), 4.62 (s, 2H, CCH C), 3.49 (s, 4H, (CH CH ) N), 3.36 (s, 2H, NCH C O), 2.85
–
2 2 2 2 2
703.2, 680.8 (d–
)
CH
–
(s, 4H, CH2N(CH2)2).
–
12a
12b
3391.2 (yNH), 1671.6 (yC O),
9.78 (s, 1H, CNHC O), 8.18 (m, 2H, phthalazine-5H,8H), 7.90 (m, 2H, phthalazine-6H,7H), 7.54
–
–
–
1521.5, 1407.7 (yC C), 818.6,
(d, J ¼ 8.4 Hz, 2H, aniline-2H,6H), 7.31 (m, 4H, Ph-2H,3H,5H,6H), 7.10 (m, 3H, Ph-4H,
–
–
–
–
2
763.2, 713.6 (d–
)
CH
aniline-3H,5H), 4.58 (s, 2H, CCH C), 3.46 (s, 4H, (CH CH ) N), 3.26 (s, 2H, NCH C O), 2.83
2
2
2 2
–
(s, 4H, CH2N(CH2)2), 2.25 (s, 3H, CCH3).
–
3264.2 (yNH), 1698.4 (yC O),
–
9.97 (s, 1H, CNHC O), 8.18 (m, 3H, aniline-3H, phthalazine-5H,8H), 7.88 (m, 2H,
–
–
1588.1, 1532.7 (yC C),
–
phthalazine-6H,7H), 7.91 (m, 2H, aniline-4H,5H), 7.32 (m, 5H, Ph-2H,3H,5H,6H þ aniline-6H),
–
768.5 (d–
)
7.18 (t, J ¼ 7.2 Hz, 1H, Ph-4H), 4.59 (s, 2H, CCH2C), 3.46 (s, 4H, (CH2CH2)2N), 3.34 (s, 2H,
CH
–
–
NCH C O), 2.89 (s, 4H, CH N(CH ) ).
–
2
2
2 2
–
12c
12d
12e
12f
20a
3276.2 (yNH), 1687.4 (yC O),
10.10 (s, 1H, CNHC O), 8.17 (m, 2H, phthalazine-5H,8H), 7.92 (m, 3H, phthalazine-6H,7H þ
–
–
–
1594.4, 1516.9 (yC C), 778.8,
aniline-2H), 7.61 (d, J ¼ 8.3 Hz, 1H, aniline-6H), 7.31 (m, 5H, Ph-2H,3H,5H,6H þ aniline-5H),
–
–
713.8, 675.1 (d–
)
CH
7.13 (m, 2H, Ph-4H, aniline-4H), 4.58 (s, 2H, CCH2C), 3.46 (s, 4H, (CH2CH2)2N), 3.30
–
–
–
(s, 2H, NCH C O), 2.83 (s, 4H, CH N(CH ) ).
2
2
2 2
–
3303.0 (yNH), 1688.4 (yC O),
10.11 (s, 1H, CNHC O), 8.18 (m, 2H, phthalazine-5H,8H), 7.89 (m, 2H, phthalazine-6H,7H),
–
–
–
1513.8, 1410.8 (yC C), 846.7,
7.82 (d, J ¼ 8.6 Hz, 2H, aniline-2H,6H), 7.29 (m, 6H, Ph-2H,3H,5H,6H þ aniline-3H,5H), 7.14
–
–
–
–
762.8, 712.8 (d–
)
CH
(t, J ¼ 7.1 Hz, 1H, Ph-4H), 4.58 (s, 2H, CCH C), 3.46 (s, 4H, (CH CH ) N), 3.31 (s, 2H, NCH C O),
2
2
2 2
2
–
2.84 (s, 4H, CH2N(CH2)2).
–
–
3282.3 (yNH), 1695.8 (yC O),
–
9.93 (s, 1H, CNHC O), 8.17 (m, 2H, phthalazine-5H,8H), 7.93 (m, 2H, phthalazine-6H,7H),
–
1506.3 (yC C), 824.4,
7.70 (m, 2H, aniline-2H,6H), 7.31 (m, 4H, Ph-2H,3H,5H,6H), 7.16 (t, J ¼ 8.9 Hz, 3H, Ph-4H,
–
–
–
aniline-3H,5H), 4.58 (s, 2H, CCH C), 3.46 (s, 4H, (CH CH ) N), 3.27 (s, 2H, NCH C O), 2.83
–
2 2 2 2 2
762.9 (d–
)
CH
–
(s, 4H, CH2N(CH2)2).
–
3282.8 (yNH), 1696.7 (yC O),
10.58 (s, 1H, CNHC O), 8.47 (s, 2H, aniline-2H,6H), 8.17 (m, 2H, phthalazine-5H,8H), 7.89
–
–
–
1532.4 (yC C), 762.4, 700.4,
(m, 2H, phthalazine-6H,7H), 7.78 (s, 1H, aniline-4H), 7.26 (m, 4H, Ph-2H,3H,5H,6H), 7.16
–
–
–
–
680.9 (d–
)
(t, J ¼ 6.9 Hz, 1H, Ph-4H), 4.58 (s, 2H, CCH C), 3.48 (s, 4H, (CH CH ) N), 3.36 (s, 2H, NCH C O),
CH
2
2
2 2
2
–
2.85 (s, 4H, CH2N(CH2)2).
–
–
3419.7 (yNH), 1690.2 (yC¼O),
1515.0, 1464.7, 1420.7 (yC C),
817.4 (d–CH).
9.76 (s, 1H, CNHC O), 7.54 (d, J ¼ 8.2 Hz, 2H, aniline-2H,6H), 7.34 (m, 6H,
phthalazine-5H,8H þ Ph-2H,3H,5H,6H), 7.13 (m, 3H, aniline-3H,5H þ Ph-4H), 4.55
–
–
(s, 2H, CCH2C), 3.94 (s, 3H, OCH3), 3.87 (s, 3H, OCH3), 3.40 (s, 4H, (CH2CH2)2N), 3.25
–
(s, 2H, NCH C O), 2.82 (s, 4H, CH N(CH ) ), 2.25 (s, 3H, CCH ).
–
2
2
2 2
3
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