772 J. Chin. Chem. Soc., Vol. 51, No. 4, 2004
Khalafallah et al.
Table 2.
Table 3.
Comp.
No.
(Calcd.) Found
Comp.
No.
1H-NMR (DMSO) d ppm
IR (umax/cm-1)
C
H
N
1
2
7
8
3.43 (s, 3H, CH3), 8.1-7.3 (m, 5H, aromatic protons
and heterocyclic hydrogen), 6.7 (s, 2H, NH2), 10.2 (s,
1H, NH).
3.44 (s, 3H, CH3), 5.73 (s, 2H, NH2), 8.01-7.48 (m,
7H, aromatic protons and heterocyclic hydrogen), 12,
41 (s, 2H, two NH).
3.42 (s, 3H, CH3), 8.11-7.25 (m, 5H, aromatic protons
and heterocyclic hydrogen), 6.65 (s, 2H, NH2), 10.22
(s, 1H, NH), 10.5 (s, 1H, OH).
3.45 (s, 3H, CH3), 8.2-7.47 (m, 7H, aromatic protons
and heterocyclic hydrogen), 5.75 (s, 2H, NH2), 10.55
(s, 1H, OH).
5.7 (s, 2H, NH2), 8.1-7.2 (m, 11H, aromatic protons
and heterocyclic hydrogens), 12.25 (br. s., 2H, 2NH).
5.76 (s, 2H, NH2), 8.01-7.1 (m, 15H, aromatic protons
and heterocyclic hydrogens), 12.24 (br. s., 1H, NH).
5.75 (s, 2H, NH2), 8.1-7.01 (m, 14H, aromatic protons
and heterocyclic hydrogens).
1
2216 (CºN), 3400-3100 (NH, (67.92) (4.18) (15.84)
NH2), 1640 (C=O). 67.90 4.15 15.80
2206 (CºN), 3350-3200 (NH, (64.70) (4.22) (16.77)
NH2), 1640 (C=O). 64.65 4.10 16.66
2220 (CºN), 3400-3100 (NH, (68.29) (4.09) (18.96)
NH2), 1655 (C=O). 68.28 4.07 18.95
2214 (CºN), 3450-3100 (NH, (65.45) (3.92) (18.17)
NH2), 1650 (C=O). 65.43 3.91 18.16
2210 (CºN), 3400-3150 (NH, (60.87) (3.41) (20.28)
NH2), 1655 (C=O). 60.86 3.40 29.27
2210 (CºN), 3400-3100 (NH, (65.75) (4.14) (19.17)
NH2), 1645 (C=O). 65.74 4.13 19.15
2208 (CºN), 3400-3100 (NH, (63.43) (3.99) (18.49)
NH2), 1640 (C=O). 63.41 3.98) 18.47
2215 (CºN), 3400-3100 (NH, (59.63) (3.54) (20.28)
2
3a
3b
3c
4a
4b
4c
3a
4a
5a
6a
NH2), 1655 (C=O).
59.62 3.52 20.27
(66.05) (3.69) (19.26)
66.04 3.68 19.25
(63.72) (3.56) (18.58)
63.71 3.55 18.57
(59.88) (3.14) (20.37)
59.87 3.12 20.35
(64.16) (3.79) (19.39)
64.15 3.78 19.38
(62.19) (3.67) (18.80)
62.18 3.65 18.79
(58.91) (3.29) (20.36)
58.90 3.27 20.35
5a
5b
5c
2218 (CºN), 3400-3100
(NH2, NH), 1645 (C=O).
2217 (CºN), 3450-3100
(NH2, NH), 1655 (C=O).
2220 (CºN), 3400-3100
(NH2, NH), 1650 (C=O).
2213 (CºN), 3450-3100
(NH2, NH), 1645 (C=O).
2215 (CºN), 3400-3100
(NH2, NH), 1644 (C=O).
2219 (CºN), 3400-3100
(NH2, NH), 1650 (C=O).
5.77 (s, 2H, NH2), 8.01-7.1 (m, 16H, aromatic protons
and heterocyclic hydrogens), 12.25 (brs. s., 1H, NH).
6a
6b
6c
solvent to give the title compounds (5a-c) and (6a-c).
Synthesis of 4-amino-2-methyl-1H-benz[g]quinoline-5,10-
dione-3-carboxylic acid (7) and 4-amino-2-methyl-1,2,3-
trihydropiperidino[2,3-b] benz[g]-1,2,3,4-trihydroquino-
line-5,6,11-trion-3-carboxilic acid (8)
7
3500-3150 (NH2, NH, OH). (63.44) (4.25) (9.85)
63.42 3.23 9.84
3350-3100 (NH2, NH, OH), (61.19) (4.28) (11.89)
1640 (C=O). 61.17 4.27 11.88
3500-3100 (NH2, NH, OH), (64.94) (4.15) (14.43)
1645 (C=O), 2206 (CºN). 64.93 4.13 14.42
3500-3100 (NH, NH2, OH), (62.38) (3.99) (13.86)
1650 (C=O), 2210 (CºN). 62.36 3.98 13.85
3500-3100 (NH, NH2, OH), (58.20) (3.49) (3.23)
1655 (C=O), 2215 (CºN). 58.19 3.47 3.22
3500-3150 (NH, NH2, OH), (63.02) (4.19) (15.31)
1645 (C=O), 2216 (CºN). 63.01 4.17 15.30
3500-3100 (NH, NH2, OH), (60.89) (4.05) (14.79)
1644 (C=O), 2220 (C=N). 60.88 4.03 14.78
3500-3150 (NH, NH2, OH), (57.37) (3.61) (16.73)
1645 (CO), 2217 (CºN). 57.36 3.60 16.72
3500-3100 (NH, NH2, OH), (63.29) (3.76) (15.38)
1640 (C=O), 2212 (CºN). 63.28 3.75 15.36
3500-3150 (NH, NH2, OH), (61.15) (3.64) (14.86)
1645 (C=O), 2213 (CºN) 61.13 3.63 14.84
3500-3100 (NH, NH2, OH), (57.60) (3.22) (16.97)
1640 (C=O), 2216 (CºN). 57.59 3.21 16.95
3500-3150 (NH, NH2, OH), (61.83) (3.84) (16.02)
1644 (C=O), 2218 (CºN). 61.81 3.82 16.01
3500-3100 (NH, NH2, OH), (60.00) (3.73) (15.55)
1645 (C=O), 2216 (CºN). 60.00 3.72 15.54
3500-3100 (NH, NH2, OH), (56.95) (3.36) (17.22)
1640 (C=C), 2214 (CºN). 56.94 3.35 17.20
8
A solution of 1 and or 2 (0.01 mole) in glacial acetic
acid (20 mL) containing a few drops of concentrated hydro-
chloric acid respectively was heated under reflux for 6-7 h.
The solvent was then evaporated under reduced pressure and
the residue treated with alkali solution of sodium hydroxide;
the solid product was collected by filtration and crystallized
from ethanol to give the title compounds.
9a
9b
9c
10a
10b
10c
11a
11b
11c
12a
12b
12c
Synthesis of azodye (9a-c) and (10a-c)
A solution of compounds 7 and or 8 (0.01 mol) in etha-
nol was reacted with diazonium salt of a different aromatic
amine (0.01 mol). The reaction product was cooled and col-
lected by filtration and crystallized from the proper solvent to
give the title compounds.
Synthesis of compounds (11a-c) and (12a-c)
A solution of compounds (9a-c) and or (10a-c) (0.01
mol) in ethanol (20 mL) was treated with ethylcyano acetate
(0.01 mol) in the presence of a few drops of piperidine; the re-
action mixture was heated under reflux for 10-12 h. The sol-