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Med Chem Res (2012) 21:844–852
Table 2 Quantity of reactants
used in synthesis
Compound
no.
Quantity of reactants
Aldehyde
Amine
0.03 mol 3-amino-1,2,4-triazole (2.5 g)
1
2
3
4
5
0.03 mol furan-2-carbaldehyde (2.5 ml)
0.024 mol naphthalene-1-carbaldehyde (3.26 g) 0.024 mol 3-amino-1,2,4-triazole (2.0 g)
0.006 mol 3-formylchromone (1.0 g)
0.006 mol p-chloroaniline (0.762 g)
0.006 mol each of 3-formylchromone (1.0 g)
0.006 mol 3-amino-1,2,4-triazole (0.5 g)
0.012 mol naphthalene-1-carbaldehyde (1.8 ml) 0.012 mol 2-amino-5-methylisoxazole
(1.2 g)
6
0.012 mol thiophene-2-carbaldehyde (1.1 ml)
0.012 mol thiophene-2-carbaldehyde (1.1 ml)
0.012 mol 3-amino-1,2,4-triazole (1 g)
7
0.012 mol p-chloroaniline (1.5 g)
8
0.024 mol naphthalene-1-carbaldehyde (3.2 ml) 0.024 mol p-chloroaniline (3.0 g)
0.03 mol naphthalene-1-carbaldehyde (4.0 ml) 3-aminopyridine (2.82 g)
9
10
0.012 mol naphthalene-1-carbaldehyde (1.8 ml) 0.012 mol 2-amino-3-methylpyridine
(1.2 ml)
1
C, 51.85; H, 3.73; N, 34.55. Found: C, 50.88; H, 3.94; N,
33.84.
C–Ostr), Mass (m/z): 241 [M ? H]?, H NMR (d ppm):
7.157–7.541 (m, 4H, aromatic); 6.993 (d, 1H, pyran); 7.520
(s, 1H, CH); 7.265 (s, 1H, CH 1,2,4-triazole); 11.447
(d, 1H, NH). Anal. Calcd. for C12H8N4O2: C, 60.00; H,
3.30; N, 16.32. Found: C, 60.99; H, 3.30; N, 17.75.
Naphthalen-1-ylmethylene-(1H-[1,2,4]triazol-3-yl)-amine
(2)
Cream powder, yield: 32% (CM), 80% (MAS), melting
range (in °C): 160–165, Rf: 0.76 (ethylacetate: n-hexane
60:40), IR (KBr, cm-1): 763 (aromatic C–Hbend), 1479
(aromatic C=Cstr), 1608 (imine HC=N), 3415 (amine
N–H), Mass (m/z): 223 [M ? H]?, 1H NMR (d ppm):
7.591–7.927 (m, 7H, aromatic); 7.954 (s, 1H, CH); 7.264
(s, 1H, CH 1,2,4-triazole); 10.410 (d, 1H, NH). Anal.
Calcd. for C13H10N4: C, 70.26; H, 4.54; N, 25.21. Found:
C, 64.53; H, 4.44; N, 26.87.
(5-methyl-5H-isoxazol-2-yl)-naphthalen-1-ylmethylene-
amine (5)
White powder, yield: 29% (CM), 73% (MAS), melting
range (in °C): 59–63, Rf: 0.80 (ethylacetate: n-hexane
60:40), IR (KBr, cm-1): 763(aromatic C–Hbend), 1431
(aromatic C=Cstr), 1516 (imine HC=N), 1088 (5-membered
1
C–Ostr), Mass (m/z): 237 [M ? H]?, H NMR (d ppm):
7.564–7.637 (m, 7H, aromatic); 7.265 (s, 1H, CH);
6.157–6.189 (m, 2H, isoxazole); 2.391 (d, 3H, CH3). Anal.
Calcd. for C15H12N2O: C, 64.25; H, 5.12; N, 11.86. Found:
C, 67.00; H, 6.11; N, 16.23.
3-[(4-chloro-phenylimino)-methyl]-chromen-4-one (3)
Yellow amorphous, yield: 48% (CM), 78% (MAS), melting
range (in °C): 120–124, Rf: 0.81 (ethylacetate: n-hexane
60:40), IR (KBr, cm-1): 670 (aromatic C–Hbend), 1470
(aromatic C=Cstr), 1650 (imine HC=N), 1013 (C–Clstr),
1067 (5-membered C–Ostr), 1216 (asymmetric C–Ostr),
Mass (m/z): 284[M ? H]?, 1H NMR (d ppm): 7.077–7.466
(m, 8H, aromatic); 5.788 (d, 1H, pyran); 7.349 (s, 1H, CH);
10.410 (d, 1H, NH). Anal. Calcd. for C16H10ClNO2: C,
64.74; H, 5.55; N, 4.94. Found: C, 64.68; H, 5.14; N, 4.10.
Thiophen-2-ylmethylene-(1H-[1,2,4]triazol-3-yl)-amine (6)
Dark brown powder, yield: 52% (CM), 80% (MAS),
melting range (in °C): 100–105, Rf: 0.66 (ethylacetate:
n-hexane 60:40), IR (KBr, cm-1): 709 (aromatic C–Hbend),
1407 (aromatic C=Cstr), 1604 (imine HC=N), 3122 (amine
N–H), Mass (m/z): 179 [M ? H]?, 1H NMR (d ppm):
7.076–7.215 (m, 3H, thiophene); 7.265 (s, 1H, CH 1,2,4-
triazole); 9.412 (d, 1H, NH). Anal. Calcd. for C7H6N4S: C,
43.09; H, 3.39; N, 34.44. Found: C, 42.89; H, 3.61; N,
35.23.
3-[(1H-[1,2,4]triazol-3-ylimino)-methyl]-chromen-4-one
(4)
Yellow powder, yield: 43% (CM), 81% (MAS), melting
range (in °C): 105–110, Rf: 0.61 (ethylacetate: n-hexane
60:40), IR (KBr, cm-1): 754 (aromatic C–Hbend), 1483
(aromatic C=Cstr), 1610 (imine HC=N), 3442 (amine
N–H), 1110 (5-membered C–Ostr), 1283 (asymmetric
(4-chloro-phenyl)-thiophen-2-ylmethylene-amine (7)
Dark brown flakes, yield: 57% (CM), 80% (MAS), melting
range (in °C): 56–60, Rf: 0.50 (ethylacetate: n-hexane
60:40), IR (KBr, cm-1): 713 (aromatic C–Hbend), 1481
123