J. Singh, D. Sharma, and R. Bansal
Vol 000
158.65 (C═O), and 164.44 ppm (C═O); FTIR (KBr, cmꢀ1
max: 3053 (C─H, aromatic), 2947 (C─H, aliphatic), 2863
(C─H, aliphatic), 1654 (C═O, amide), 1585 (C═C, aromatic),
1448 (CH2 bending), 1256 (C─N), and 1117 (C─O─C); MS
(ESI) m/z: 307.2 [M + H]+; Anal. calcd. for C15H22N4O3: C,
)
and N─CH2, piperazine, J = 4.84 Hz), 3.68 (s, 2H,
─NCH2, piperazine), 3.78 (t, 4H, ─O(CH2)2, morpholine,
J = 5.60 Hz), 3.81 (s(br), 2H, ─NCH2, piperazine) 4.89
(s, 2H, ─NCH2), 6.94 (m, 4H, ArH, phenylpiperazine
and 5-CH, pyridazinone), 7.14 (d, 1H, 4-CH,
J = 9.96 Hz, pyridazinone), and 7.30 ppm (t, 2H, ArH,
phenylpiperazine, Jo = 7.92 Hz); 13C-NMR (400 MHz,
CDCl3): δ 42.03 (CH2), 44.89 (CH2), 46.89 (2× CH2),
49.32 (CH2), 49.56 (CH2), 52.71 (CH2CO), 66.38 (2×
CH2), 116.75 (ArCH), 116.86 (ArCH), 120.68 (ArCH),
125.43 (ArCH), 129.29 (2× ArCH), 131.13 (ArCH),
149.06 (ArC), 150.87 (ArC), 158.57 (C═O), and
164.89 ppm (C═O); FTIR (KBr, cmꢀ1) υmax: 3050
(C─H, aromatic), 2970 (C─H, aliphatic), 2849 (C─H,
aliphatic), 1660 (C═O, amide), 1584 (C═C, aromatic),
1456 (CH2 bending), 1237 (C─N), and 1113 (C─O─C);
MS (ESI) m/z: 384.3 [M + H]+; Anal. calcd. for
C20H25N5O3: C, 62.67; H, 6.54; N, 18.27. Found: C,
62.90; H, 6.72; N, 18.01.
υ
58.81; H, 7.24; N, 18.29. Found: C, 59.06; H, 6.99; N, 18.29.
2-(2-(3-Methylpiperidin-1-yl)-2-oxoethyl)-6-(morpholin-4-yl)
pyridazin-3(2H)-one (8a).
Yield: 0.42 g (50.00%); mp.
1
138–140°C; H-NMR (400 MHz, CDCl3): δ 0.92 (m, 3H,
─C(CH3)H-, piperidine), 1.15–1.19 (m, 1H, ─CH(H)─,
piperidine), 1.46–1.76 (m, 3H, ─CH(H)─ and ─CH2─,
piperidine), 1.83 (d, 1H, ─C(CH3)H, piperidine
J = 13.12 Hz), 2.29 (t) and 3.02 (t) (1:1, 1H, ─NCH(H),
piperidine J = 12.44 Hz), 2.69 (p, 1H, ─NCH(H),
J = 13.12 Hz), 3.23 (t, 4H, ─N(CH2)2, morpholine,
J = 4.64 Hz), 3.67 (dd, 1H, ─NCH(H), J = 13.28 Hz),
3.77 (t, 4H, ─O(CH2)2, morpholine, J = 4.64 Hz), 4.38
(d, 1H, ─NCH(H), J = 13.0 Hz), 4.83 (m, 2H, ─NCH2),
6.90 (d, 1H, 5-CH, pyridazinone, J = 9.92 Hz), and
7.12 ppm (d, 1H, 4-CH, pyridazinone, J = 9.96 Hz); 13C-
NMR (400 MHz, CDCl3): δ 19.00 (CH3), 25.69 (CH2),
30.85 (CH2), 31.61 (CH2), 45.46 (CH2), 46.91 (2× CH2),
49.60 (CH2), 52.40 (CH2CO), 66.40 (2× ─CH2), 125.33
(ArCH), 131.11 (ArCH), 148.98 (ArC), 158.64 (C═O),
and 164.44 ppm (C═O); FTIR (KBr, cmꢀ1) υmax: 3066
(C─H, aromatic), 2933 (C─H, aliphatic), 2854 (C─H,
aliphatic), 1653 (C═O, amide), 1594 (C═C, aromatic),
1455 (CH2, bending), 1258 (C─N), and 1116 (C─O─C);
MS (ESI) m/z: 321.3 [M + H]+; Anal. calcd. for C16H24
N4O3: C, 59.98; H, 7.54; N, 17.48. Found: C, 60.23; H,
2-(2-(4-(4-Nitrophenyl)piperazin-1-yl)-2-oxoethyl)-6-(morpholin-4-
yl)pyridazin-3(2H)-one (11a). Yield: 0.42 g (50.00%); mp. 206–
208°C; 1H-NMR (400 MHz, CDCl3): δ 3.23 (t, 4H, ─N(CH2)2,
morpholine, J = 4.82 Hz), 3.48 (t(br), 2H, ─N(CH2), piperazine,
J = 4.72 Hz), 3.53 (s (br), 2H, ─NCH2, piperazine), 3.72 (t(br),
2H, ─NCH2, piperazine, J = 4.68 Hz), 3.77 (t, 4H, ─O(CH2)2,
morpholine, J = 4.80 Hz), 3.80 (t(br), 2H, ─NCH2, piperazine
J = 4.68 Hz), 4.87 (s, 2H, ─NCH2), 6.82 (d, 2H, ArH,
phenylpiperazine, Jo = 9.36 Hz), 6.89 (d, 1H, 5-CH,
pyridazinone, J = 9.96 Hz), 7.14 (d, 1H, 4-CH, pyridazinone,
J = 9.96 Hz), and 8.13 ppm (d, 2H, ArH, phenylpiperazine,
Jo = 9.32 Hz); 13C-NMR (400 MHz, CDCl3): δ 41.35 (CH2),
44.22 (CH2), 46.79 (2× CH2), 46.87 (2× CH2), 52.71
(CH2CO), 66.36 (2× CH2), 113.02 (2× ArCH), 125.58
(ArCH), 125.99 (2× ArCH), 131.07 (ArCH), 139.17 (ArC),
149.17 (ArC), 154.31 (ArC), 158.56 (C═O), and 165.23 ppm
(C═O); FTIR (KBr, cmꢀ1) υmax: 3059 (C─H, aromatic),
2943 (C─H, aliphatic), 1666 (C═O, amide), 1588 (C═C,
aromatic), 1448, 1325 (NO2 stretch), 1234 (C─N), and 1110
(C─O─C); MS (ESI) m/z: 429.3 [M + H]+; Anal. calcd. for
C20H24N6O5: C, 56.06; H, 5.64; N, 19.61. Found: C, 55.84;
H, 5.35; N, 19.42.
7.25; N, 17.67.
2-(2-(4-Methylpiperazin-1-yl)-2-oxoethyl)-6-(morpholin-4-yl)
pyridazin-3(2H)-one (9a).
Yield: 0.42 g (61.76%); mp.
1
192–194°C; H-NMR (400 MHz, CDCl3): δ 2.25 (s, 3H,
─NCH3), 2.35 (t, 2H, ─NCH2, piperazine, J = 4.80 Hz),
2.40 (t, 2H, ─NCH2, piperazine, J = 4.62 Hz), 3.16 (t,
4H, ─N(CH2)2, morpholine, J = 4.70 Hz), 3.44 (t, 2H,
─NCH2, piperazine, J = 4.70 Hz), 3.59 (s(br), 2H,
─NCH2, piperazine), 3.71 (t, 4H, ─O(CH2)2, morpholine,
J = 4.66 Hz), 4.77 (s, 2H, ─NCH2─), 6.83 (d, 1H, 5-CH,
pyridazinone, J = 9.96 Hz), and 7.06 ppm (d, 1H, 4-CH,
pyridazinone, J = 9.96 Hz); 13C-NMR (400 MHz,
CDCl3): δ 41.91 (CH3), 44.68 (CH2), 45.97 (CH2), 46.87
(2× CH2), 52.72 (CH2), 54.42 (CH2), 54.70 (CH2CO),
66.38 (2× CH2), 125.43 (ArCH), 131.09 (ArCH), 149.05
(ArC), 158.61 (C═O), and 164.75 ppm (C═O); FTIR
(KBr, cmꢀ1) υmax: 2851 (C─H, aliphatic), 1659 (C═O,
amide), 1583 (C═C, aromatic), 1450 (CH2, bending),
1254 (C─N), and 1113 (C─O─C); MS (ESI) m/z: 322.2
[M + H]+; Anal. calcd. for C15H23N5O3: C, 56.06; H,
2-(2-(4-(4-Fluorophenyl)piperazin-1-yl)-2-oxoethyl)-6-(morpholin-
4-yl)pyridazin-3(2H)-one (12a).
Yield: 0.12 g (48.00%); mp.
1
172–174°C; H-NMR (400 MHz, CDCl3): δ 3.18 (t, 4H,
─N(CH2)2, morpholine, J = 4.78 Hz), 3.25 (s(br), 8H, 2×
─N(CH2)2, piperazine), 3.74 (t, 4H, ─O(CH2)2, morpholine,
J = 4.76 Hz), 4.59 (s, 2H, ─NCH2─), 6.81 (d, 1H, 5-CH,
pyridazinone, J = 9.88 Hz), 6.85–6.89 (m, 2H, ArH), 6.98 (t,
2H, ArH, Jo = 8.70 Hz,), and 7.04 ppm (d, 1H, 4-CH,
pyridazinone, J = 9.88 Hz); 13C-NMR (400 MHz, CDCl3): δ
43.37 (2× CH2), 46.89 (2× CH2), 47.94 (2× CH2), 56.50
(CH2CO), 66.37 (2× CH2), 115.64 (ArCH), 115.86 (ArCH),
118.81 (ArCH), 118.89 (ArCH), 124.99 (ArCH), 131.04
(ArCH), 147.17 (ArC), 147.19 (ArC), 148.83 (ArC), 156.59
7.21; N, 21.79. Found: C, 56.32; H, 6.97; N, 21.66.
2-(2-(4-Phenylpiperazin-1-yl)-2-oxoethyl)-6-(morpholin-4-yl)
pyridazin-3(2H)-one (10a). Yield: 0.31 g (41.33%); mp.
1
204–206°C; H-NMR (400 MHz, CDCl3): δ 3.21 (s, 2H,
─NCH2, piperazine), 3.24 (t, 6H, ─N(CH2)2, morpholine
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet