M. Kumar Jangid, T. Yadav, and A. K. Yadav
Vol 000
mixture was irradiated for 10 min at 120ꢀC. The product was
extracted by ethylacetate (3 ꢂ 10 mL), and the solvent was
removed by distillation under reduced pressure (10 mm Hg) at
60ꢀC to give products 8a–d. The product was recrystallized
from 2-propanol.
3-[20(Benzylidenehydrazinyl)-6-chloropyridazine 8a. White
solid; mp 254–256ꢀC; 1H NMR (DMSO-d6) d 7.54–7.70 (m, 7H),
8.14 (s, 1H), 11.72 (s, 1H); IR (KBr) nmax 3024, 2921, 2847,
1614, 1593, 1530, 1413, 1064, 751, 687 cmꢃ1; Anal. Calcd for
C11H9ClN4: C, 56.78, H, 3.90, N, 20.48; Found: C, 56.63, H,
3.87, N, 24.01.
3-[20-(400-Methoxybenzylidene)hydrazinyl]-6-chloropyridazine
8b. White solid, mp 260–263ꢀC; 1H NMR (DMSO-d6) d 3.50 (s,
3H), 7.40–7.72 (m, 6H), 8.0 (s, 1H), 11.68 (s, 1H); IR (KBr) nmax
3028, 2995, 2950, 2847, 1614, 1582, 1530, 1440, 1135, 751,
687 cmꢃ1; Anal. Calcd for C12H11OClN4: C, 54.86, H, 4.22, N,
21.32; Found : C, 54.77, H, 4.17, N, 21.24.
Calcd for C25H28O2N4: C, 72.09, H, 6.78, N, 13.45; Found: C,
71.95, H, 6.75, N, 13.41.
2-[60-(400-Benzylpiperidin-1-yl)pyridazin-3-yl]-2-(4000-methyl-
phenyl)acetamide 10g. White solid; mp 214–217ꢀC; 1H NMR
(CDCl3) d 1.25 (s, 2H), 1.70 (s, 3H), 1.82 (s, 3H), 2.50 (m, 2H),
3.20 (m, 2H), 3.40 (bs, 2H), 4.22 (d, J = 9.2 Hz, 2H,), 5.20 (s,
1H), 7.09–8.00 (m, 11H); IR (KBr) nmax 3412, 3215, 2995, 2920,
1684, 1640, 1580, 1216, 1174, 1121, 1034, 690, 605cmꢃ1; Anal.
Calcd for C25H28O N4: C, 74.97, H, 7.04, N, 13.98; Found : C,
74.91, H, 6.99, N, 13.94.
2-[40-Methylphenyl]-2-[600-(400-phenylpiperazin-1-yl)pyridazin-
3-yl]acetamide 10h.
White solid; mp 100–122ꢀC; 1H NMR
(CDCl3) d 1.80 (s, 3H), 3.55 (s, 4H), 3.80 (s, 4H), 5.10 (s, 1H),
5.84 (bs, 1H), 6.75–7.55 (m, 12H); IR (KBr) nmax 3375, 3185,
2847, 1678, 1597, 1492, 1445, 1386, 1231, 759 cmꢃ1; Anal. Calcd
for C23H25ON5: C, 71.29, H, 6.50, N, 18.07; Found: C, 71.22, H,
6.44, N, 18.02.
General procedure for the synthesis of 13a–f.
The
3-(2-Benzylidenehydrazinyl)-6-methoxypyridazine 8c. White
solid; mp 260–263ꢀC; 1H NMR (DMSO-d6) d 3.68 (s, 3H), 7.30–
7.66 (m, 7H) 8.15 (s, 1H), 11.50 (s, 1H): IR (KBr) nmax 3024,
2985, 2921, 2847, 1614, 1593, 1545, 1145, 1135, 687 cmꢃ1; Anal.
Calcd for C12H12ON4: C, 63.14, 5.29, N, 24.54; Found: C, 63.05,
H, 5.23, N, 24.47.
appropriate isocyanate/isothiocyanate (0.003 M) and compound 12
(0.003 M) were added to [BMIM]OH (5 mL). The resulting
mixture was subjected to microwave irradiation for 10min at
120ꢀC. The compound was extracted by ethylacetate (3ꢂ 10mL)
under reduced pressure (10mmHg) at 60ꢀC to give products
13a–f. The product was crystallized with dilute acetic acid (5 mL).
3-[20(400-Methoxybenzylidene)hydrazinyl]-6-methoxypyridazine
1
N-Phenyl-N0-(6-phenylpyridazin-3-yl)urea 13a.
Creamy
8d. White solid; mp 265–267ꢀC; H NMR (DMSO-d6) d 3.50
1
solid, mp 305ꢀC; H NMR (DMSO-d6) d 9.83 (s, 1H), 9.76 (s,
1H), 8.22 (d, J = 9.2 Hz, 1H), 7.95 (d, J =9.2 Hz, 1H), 8.04–8.12
(m, 3H), 7.50–7.58 (m, 3 H), 7.34 (d, J = 7.6 Hz, 1H ꢂ 2), 7.03 (d,
J = 7.6Hz, 1Hꢂ 2); Anal. Calcd for C17H14ON4: C, 70.33, H,
4.86, N, 19.30; Found: C, 70.25, H, 4.81, N, 19.17.
(s, 3H), 3.65 (s, 3H), 7.37–7.67 (m, 6H), 8.10 (s, 1H), 11.68
(s, 1H); IR (KBr) nmax 3028, 2990, 2950, 2847, 1614, 1582,
1530, 1440, 1135, 751, 687cmꢃ1; Anal. Calcd for C13H14ON4: C,
60.45, 5.46, N, 21.96; Found: C, 60.38, H, 5.43, N, 21.88.
General procedure for the synthesis of 9a–f and
N-(4-Chlorophenyl)-N0-(6-phenylpyridazin-3-yl)urea 13b.
White solid, mp 300ꢀC; 1H NMR (DMSO-d6) d 9.87 (s, 1H), 9.85
(s, 1H), 8.24 (d, J = 9.2 Hz, 1H), 7.95 (d, J = 9.2 Hz, 1H), 8.06–8.12
(m, 3H), 7.48–7.55 (m, 2H), 7.35 (d, J = 8.8 Hz, 2H ꢂ 2); Anal.
Calcd for C17H13ClN4O: C, 62.87, H, 4.03, N, 17.25; Found : C,
63.60, H, 3.96, N, 17.20.
10a–h.
Compounds 5a–f/6a–h were dissolved in concentrated
sulfuric acid (5 mL), and then, reaction mixture was refluxed for
1 h. The products 9a–f/10a–h were extracted with ethyl acetate
(3 ꢂ 10mL). The solvent was removed by distillation under
reduced pressure (10 mmHg) at 60ꢀC, and the product was
recrystallized by 2-propanol. The physicochemical characteristics
of some important compounds are present next:
N-(4-Methylphenyl)-N0-(6-phenylpyridazin-3-yl)urea
13c.
White solid, mp 285ꢀC; 1H NMR (DMSO-d6) d 9.81
2-(40-Methoxyphenyl)-2-(60-methoxypyridazin-3-yl)acetamide
9d. White solid; mp 78–80ꢀC; 1H NMR (CDCl3) d 3.82 (s, 3H),
3.90 (s, 3H), 5.40 (s, 1H), 7.30–7.65 (m, 6H), 7.66–7.85 (m, 2H);
IR (KBr) nmax 3325, 3205, 2995, 1669, 1624, 1410, 1152,
702 cmꢃ1; Anal. Calcd for C14H15O3N3: C, 61.52, H, 5.54, N,
15.37, Found: C, 61.48, H, 5.49, N, 15.33.
(s, 1H), 9.72 (s, 1H), 8.20 (d, J = 9.2 Hz, 1H), 8.05–8.10 (m,
2H), 7.50–7.58 (m, 4H), 7.40 (d, J = 8 Hz, 2H), 7.15 (d,
J = 8 Hz, 2H), 2.26 (s, 3H); Anal. Calcd for C18H16N4O: C,
71.04, H, 5.30, N, 18.41; Found: C, 70.95, H, 5.17, N, 18.23.
N-Phenyl-N0-(6-phenylpyridazin-3-yl)thiourea 13d.
White
1
solid; mp 200ꢀC; H NMR (DMSO-d6) d 13.50 (s, 1H), 11.20 (s,
1H), 8.31 (d, J=9.6 Hz, 1H), 8.10 (d, J=6.4 Hz, 2H), 7.50–7.70
(m, 6H), 7.45 (t, J=8 Hz, 2H), 7.25 (t, J=8 Hz, 1H); Anal. Calcd
for C17H14N4S: C, 66.64, H, 4.61, N, 18.29, S, 10.47; Found : C,
66.60, H, 4.55, N, 18.15; S, 10.30.
2-(60-Methoxypyridazin-3-yl)-2-(400-methylphenyl)acetamide
1
9e. White solid; mp 218–220ꢀC; H NMR (CDCl3) d 1.72 (s,
3H), 3.75 (s, 3H), 5.45 (s, 1H), 6.70–7.30 (m, 6H), 7.65–7.90 (m,
2H); IR (KBr) nmax 3365, 3195, 2975, 1628, 1480, 1420, 1150,
820, 650 cmꢃ1; Anal. Calcd for C14H15O2N3: C, 65.34, H, 5.88,
N, 16.33; Found: C, 65.29, H, 5.82, N, 16.29.
N-(4-Chlorophenyl)-N0-(6-phenylpyridazin-3-yl)thiourea
13e.
White solid, mp 200ꢀC; 1H NMR (DMSO-d6) d 13.50
2-(40-Chlorophenyl)-2-(600-methoxypyridazin-3-yl)-acetamide
1
9f. White solid; mp 220–222ꢀC, H NMR (CDCl3) d 3.80 (s,
(s, 1H), 8.32 (d, J=9.6 Hz, 1H), 8.10 (d, J=6.4 Hz, 2H),
7.52–7.70 (m, 9H); Anal. Calcd for C17H13ClN4S: C, 59.91, H,
3.84, N, 16.44, S, 9.41; Found : C, 59.80, H, 3.75, N, 16.30; s, 9.42.
N-(4-Methylphenyl)-N0-(6-phenylpyridazin-3-yl)thiourea
3H), 5.38 (s, 1H), 7.30–7.66 (m, 6H), 7.70–7.90 (m, 2H); IR
(KBr) nmax 3365, 3193, 2970, 1628, 1487, 1415, 1158, 820,
648 cmꢃ1; Anal. Calcd for C13H12O2Cl N3: C, 56.22, H, 4.41, N,
15.13; Found: C, 56.18, H, 4.38, N, 15.08.
13f.
White solid, mp 198ꢀC; 1H NMR (DMSO-d6) d 13.45
2-[60-(400-Benzylpiperidin-1-yl)pyridazin-3-yl]-2-(4000-methoxy-
(s, 1H), 8.33 (d, J=9.2 Hz, 1H), 8.06 (d, J=6.4 Hz, 2H), 7.70
(d, J=9.6 Hz, 1H), 7.50–7.60 (m, 6H), 7.25 (d, J=8 Hz, 2H), 2.35
(s, 3H): Anal. Calcd for C18H16N4S: C, 67.47, H, 5.08, N, 17.49, S,
10.01; Found : C, 67.40, H, 4.92, N, 17.52; S, 9.95.
General procedure for the synthesis of 14a–c. Substituted
benzenesulfonyl chloride (0.005 M) and compound 12 (0.005 M)
1
phenyl) acetamide 10f. White solid; mp 243–245ꢀC; H NMR
(CDCl3) d 1.25 (m, 2H), 1.60 (m, 3H), 2.50 (m, 2H), 2.90 (m, 2H),
3.40 (bs, 2H), 3.72 (s, 3H), 4.25 (d J=12.8 Hz, 2H), 5.07 (s, 1H)
6.75–785 (m, 11H); IR (KBr) nmax 3425, 3196, 2995, 2920, 2851,
1679, 1650, 1600, 1495, 1450, 1180, 1032, 010, 621 cmꢃ1; Anal.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet