D. Kaushik et al. / European Journal of Medicinal Chemistry 45 (2010) 3960e3969
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10e12 h. The excess of alcohol was distilled off and cooled. Filtered
off crystals of the acid hydrazide (4ael), and recrytallised from
6.1.4.9. 5-Benzylidene-2-(2-chloro-benzoyl)-3-phenyl-2,5-dihydro-
1H-[1,2,4] triazin-6-one (5 aIX). 1H NMR(DMSO-d6) (
, ppm) 11.70
d
ethanol. The physical data of the hydrazides are given in Table 8.
(s, 1H, CONH), 8.37e8.35 (d, 2H, Ar-H), 8.05e8.03 (d, 2H, Ar-H),
7.66e7.51 (m, 10H, Ar-H), 7.31 (s, 1H, CH]C).
6.1.4. General procedure for the synthesis of Triazinone (5 aIefXII)
An equimolar quantity of 4-benzylidene-2-phenyl-4H-oxazol-5-
one (2aef) derivative (0.01 mol), substituted acid hydrazide (4ael)
(0.01 mol) and sodium acetate (0.2 g) in gl. acetic acid (10 ml) was
refluxed for 8e10 h. The reaction mixture was poured into crushed
ice and stirred. The solid obtained was filtered, washed with water,
dried and recrystallised from ethanol. The physical data of all the
synthesized compounds are given in Table 1.
The synthesized compounds (Scheme 1) showed characteristic
absorption bands in IR spectra: 3450, 3328e3303 (NH), 1737e1690
(CONH), 1696e1662 (C]O), 1628e1604 (C]N, imine), 1300e1400
(CeN, Ar-NH).
6.1.4.10. 5-Benzylidene-2-(4-fluoro-benzoyl)-3-phenyl-2,5-dihydro-
1H-[1,2,4] triazin-6-one (5 aX). 1H NMR(DMSO-d6) (
d, ppm) 11.61
(s, 1H, CONH), 8.38e8.36 (d, 2H, Ar-H), 8.05e8.03 (d, 2H, Ar-H),
7.87e7.47 (m, 8H, Ar-H), 7.28 (s, 1H, CH]C), 7.24e7.22 (d, 2H, Ar-
H).
6.1.4.11. 5-Benzylidene-2-(2-phenoxy-acetyl)-3-phenyl-2,5-dihydro-
1H-[1,2,4] triazin-6-one (5 aXI). 1H NMR(DMSO-d6) (
d, ppm) 11.56
(s, 1H, CONH), 8.25e8.23 (d, 2H, Ar-H), 8.07e8.05 (d, 2H, Ar-H),
7.76e7.48 (m, 6H, Ar-H), 7.27 (s, 1H, CH]C), 7.24e7.22 (d, 2H, Ar-H),
6.91e6.82 (m, 3H, Ar-H), 5.11 (s, 2H, CH2).
6.1.4.1. 2-Benzoyl-5-benzylidene-3-phenyl-2,5-dihydro-1H-[1,2,4]
6.1.4.12. 5-Benzylidene-2-[2-(4-isobutyl-phenyl)-propionyl]-3-
triazin-6-one (5 aI). 1H NMR(DMSO-d6) (
d, ppm) 11.57 (s, 1H,
phenyl-2,5-dihydro-1H-[1,2,4] triazin-6-one (5 aXII). 1H NMR
CONH), 8.38e8.35 (d, 2H, Ar-H), 8.22e8.19 (d, 2H, Ar-H), 7.97e7.95
(t, 2H, Ar-H), 7.88e7.86 (d, 2H, Ar-H), 7.62e7.60 (t, 1H, Ar-H),
7.48e7.35 (m, 6H, Ar-H), 7.27 (s, 1H, CH]C). Mass spectra: Mþ
(367), M-1 (366), M-105, M-77.
(DMSO-d6) (d, ppm) 11.59 (s, 1H, CONH), 8.27e8.25 (d, 2H, Ar-H),
8.01e7.99 (d, 2H, Ar-H), 7.83e7.81 (d, 2H, Ar-H), 7.65e7.34 (m, 8H,
Ar-H), 7.29 (s, 1H, CH]C), 3.95 (q, 1H, eCH(methyl)-), 2.59 (d, 2H,
eCH2e), 2.18 (m, 1H, CH), 1.57 (d, 3H, CH3), 1.21 (d, 6H, 2 X CH3).
6.1.4.2. 5-Benzylidene-2-(4-methyl-benzoyl)-3-phenyl-2,5-dihydro-
6.1.4.13. 2-Benzoyl-5-(4-methyl-benzylidene)-3-phenyl-2,5-dihydro-
1H-[1,2,4] triazin-6-one (5 aII). 1H NMR(DMSO-d6) (
d, ppm) 11.61
1H-[1,2,4] triazin-6-one (5 bI). 1H NMR(DMSO-d6) (
d, ppm) 11.60
(s, 1H, CONH), 8.27e8.25 (d, 2H, Ar-H), 8.03e8.00 (d, 2H, Ar-H),
7.81e7.7 (d, 2H, Ar-H), 7.65e7.56 (m, 4H, Ar-H), 7.42e7.34 (m, 4H,
Ar-H), 7.29 (s, 1H, CH]C), 2.38 (s, 3H, CH3).
(s, 1H, CONH), 8.36e8.34 (d, 2H, Ar-H), 8.12e8.10 (d, 2H, Ar-H),
7.88e7.86 (d, 2H, Ar-H), 7.74e7.49 (m, 6H, Ar-H), 7.31 (s, 1H, CH]C),
7.28e7.26 (d, 2H, Ar-H), 2.37 (s, 3H, CH3).
6.1.4.3. 5-Benzylidene-2-(4-nitro-benzoyl)-3-phenyl-2,5-dihydro-
6.1.4.14. 2-(4-Methyl-benzoyl)-5-(4-methyl-benzylidene)-3-phenyl-
1H-[1,2,4] triazin-6-one (5 aIII). 1H NMR(DMSO-d6) (
d, ppm) 11.54
2,5-dihydro-1H-[1,2,4] triazin-6-one (5 bII). 1H NMR(DMSO-d6) (
d,
(s, 1H, CONH), 8.40e8.38 (d, 2H, Ar-H), 8.26e8.24 (d, 2H, Ar-H),
7.95e7.93 (d, 2H, Ar-H), 7.76e7.54 (m, 5H, Ar-H), 7.47e7.39 (m, 3H,
Ar-H), 7.26 (s, 1H, CH]C).
ppm) 11.60 (s, 1H, CONH), 8.27e8.25 (d, 2H, Ar-H), 8.03e8.00 (d,
2H, Ar-H), 7.81e7.78 (d, 2H, Ar-H), 7.58e7.56 (m, 3H, Ar-H), 7.29 (s,
1H, CH]C), 7.18e7.14 (m, 4H, Ar-H), 2.38 (s, 6H, CH3).
6.1.4.4. 5-Benzylidene-3-phenyl-2-(pyridine-4-carbonyl)-2,5-dihy-
6.1.4.15. 2-[2-(4-Chloro-phenyl)-acetyl]-5-(4-methyl-benzylidene)-
dro-1H-[1,2,4] triazin-6-one (5 aIV). 1H NMR(DMSO-d6) (
d
, ppm)
3-phenyl-2,5-dihydro-1H-[1,2,4] triazin-6-one (5 bV). 1H NMR
11.61 (s, 1H, CONH), 8.98e9.01 (d, 2H, Pyridine), 8.31e8.29 (d, 2H,
Ar-H), 8.14e8.12 (d, 2H, Ar-H), 8.01e7.99 (d, 2H, pyridine),
7.73e7.64 (m, 3H, Ar-H), 7.55e7.51 (m, 3H, Ar-H), 7.29 (s, 1H, CH]
C).
(DMSO-d6) (d, ppm) 11.64 (s, 1H, CONH), 8.35e8.33 (d, 2H, Ar-H),
8.14e8.12 (d, 2H, Ar-H), 7.88e7.49 (m, 5H, Ar-H), 7.35e7.33 (d, 2H,
Ar-H), 7.28 (s, 1H, CH]C), 7.25e7.23 (d, 2H, Ar-H), 3.61 (s, 2H, CH2),
2.38 (s, 3H, CH3).
6.1.4.5. 5-Benzylidene-2-[2-(4-chloro-phenyl)-acetyl]-3-phenyl-2,5-
6.1.4.16. 2-(4-Chloro-benzoyl)-5-(4-methyl-benzylidene)-3-phenyl-
dihydro-1H-[1,2,4] triazin-6-one (5 aV). 1H NMR(DMSO-d6) (
d
,
2,5-dihydro-1H-[1,2,4] triazin-6-one (5 bVIII). 1H NMR(DMSO-d6)
ppm) 11.56 (s, 1H, CONH), 8.32e8.29 (d, 2H, Ar-H), 8.14e8.12 (d, 2H,
Ar-H), 7.86e7.47 (m, 6H, Ar-H), 7.33e7.35 (d, 2H, Ar-H), 7.28 (s, 1H,
CH]C), 7.25e7.23 (d, 2H, Ar-H), 3.61 (s, 2H, CH2).
(d, ppm) 11.61 (s, 1H, CONH), 8.38e8.35 (d, 2H, Ar-H), 8.13e8.11 (d,
2H, Ar-H), 7.84e7.51 (m, 7H, Ar-H), 7.31 (s, 1H, CH]C), 7.18e7.16 (d,
2H, Ar-H), 2.37 (s, 3H, CH3).
6.1.4.6. 5-Benzylidene-2-(2-naphthalen-1-yl-acetyl)-3-phenyl-2,5-
6.1.4.17. 5-(4-Methyl-benzylidene)-2-(2-phenoxy-acetyl)-3-phenyl-
dihydro-1H-[1,2,4] triazin-6-one (5 aVI). 1H NMR(DMSO-d6) (
d
,
2,5-dihydro-1H-[1,2,4] triazin-6-one (5 bXI). 1H NMR(DMSO-d6) (
d,
ppm) 11.48 (s, 1H, CONH), 8.22e8.20 (m, 3H, Ar-H), 7.91e7.84 (m,
5H, Ar-H), 7.60e7.58 (d, 2H, Ar-H), 7.51e7.38 (m, 5H, Ar-H),
7.33e7.31 (d, 2H, Ar-H), 7.24 (s, 1H, CH]C), 4.11 (s, 2H, eCH2e).
ppm) 11.66 (s, 1H, CONH), 8.25e8.23 (d, 2H, Ar-H), 8.03e8.01 (d,
2H, Ar-H), 7.73e7.41 (m, 6H, Ar-H), 7.24 (s, 1H, CH]C), 7.11e6.92
(m, 4H, Ar-H), 5.16 (s, 2H, CH2), 2.37 (s, 3H, CH3).
6.1.4.7. 5-Benzylidene-2-(4-methoxy-benzoyl)-3-phenyl-2,5-dihy-
6.1.4.18. 5-(4-Hydroxy-benzylidene)-2-(4-methyl-benzoyl)-3-
dro-1H-[1,2,4] triazin-6-one (5 aVII). 1H NMR(DMSO-d6) (
d, ppm)
phenyl-2,5-dihydro-1H-[1,2,4] triazin-6-one (5 cII). 1H NMR(DMSO-
11.56 (s, 1H, CONH), 8.28e8.26 (d, 2H, Ar-H), 8.03e8.01 (d, 2H, Ar-
H), 7.73e7.51 (m,6H, Ar-H), 7.27e7.25 (d, 2H, Ar-H), 7.23 (s,1H, CH]
C), 7.12e7.09 (d, 2H, Ar-H), 3.85 (s, 3H, OCH3).
d6) (d, ppm) 11.65 (s, 1H, CONH), 10.48 (s, 1H, OH), 8.31e8.29 (d, 2H,
Ar-H), 8.12e8.10 (d, 2H, Ar-H), 7.93e7.91 (d, 2H, Ar-H), 7.71e7.52
(m, 5H, Ar-H), 7.23 (s, 1H, CH]C), 7.03e7.01 (d, 2H, Ar-H), 2.34 (s,
3H, CH3).
6.1.4.8. 5-Benzylidene-2-(4-chloro-benzoyl)-3-phenyl-2,5-dihydro-
1H-[1,2,4] triazin-6-one (5 aVIII). 1H NMR(DMSO-d6) (
11.70 (s, 1H, CONH), 8.38e8.35 (d, 2H, Ar-H), 8.03e8.01 (d, 2H, Ar-
H), 7.72e7.49 (m, 10H, Ar-H), 7.31 (s, 1H, CH]C).
d
, ppm)
6.1.4.19. 2-(4-Fluoro-benzoyl)-5-(4-hydroxy-benzylidene)-3-phenyl-
2,5-dihydro-1H-[1,2,4] triazin-6-one (5 cX). 1H NMR(DMSO-d6) (
d,
ppm) 11.56 (s, 1H, CONH), 10.40 (s, 1H, OH), 7.28e7.26 (d, 2H, Ar-H),