3226
X. Wang et al.
PAPER
H, NH), 3.82–3.74 (m, 1 H, H-5), 2.83 (dd, J = 6.6, 16.1 Hz, 1 H,
H-4a), 2.45 (dd, J = 8.5, 16.3 Hz, 1 H, H-4b), 1.34 (d, J = 6.4 Hz, 3
H, CH3).
13C NMR (100 MHz, CDCl3): d = 172.0, 138.9, 128.7, 124.2, 118.3,
51.1, 42.8, 18.7.
13C NMR (100 MHz, CDCl3): d = 170.6, 136.3, 134.1, 129.3, 128.9,
128.3, 126.5, 118.4, 41.5, 29.7, 20.9.
MS (ESI+): m/z (%) = 275 (27.1, [M + Na]+), 251 (100, [M – H]+).
Anal. Calcd for C16H16N2O: C, 76.16; H, 6.39; N, 11.10. Found: C,
76.32; H, 6.42; N, 11.14.
MS (ESI+): m/z (%) = 199 (100, [M + Na]+), 177 (48.3, [M + H]+),
175 (66.1, [M – H]+).
5-Methyl-2-p-tolylpyrazolidin-3-one (4bd)
White powder; mp 76–79 °C.
IR (KBr): 3475, 3415, 3128, 1682, 1618, 1400 cm–1.
Anal. Calcd for C10H12N2O: C, 68.16; H, 6.86; N, 15.90. Found: C,
67.95; H, 6.91; N, 15.93.
1H NMR (400 MHz, CDCl3): d = 7.69 (d, J = 8.8 Hz, 2 H, ArH),
7.13 (d, J = 8.8 Hz, 2 H, ArH), 4.48 (br s, 1 H, NH), 3.75–3.74 (m,
1 H, H-5), 2.79 (dd, J = 6.8, 16.3 Hz, 1 H, H-4a), 2.41 (dd, J = 8.4,
16.3 Hz, 1 H, H-4b), 2.31 (s, 3 H, CH3), 1.31 (d, J = 6.4 Hz, 3 H,
CH3).
13C NMR (100 MHz, CDCl3): d = 171.7, 136.6, 133.8, 129.2, 118.4,
51.0, 42.7, 20.9, 18.6.
5-(Furan-2-yl)-2-phenylpyrazolidin-3-one (4ae)
White powder; mp 70–72 °C.
IR (KBr): 3223, 3118, 2901, 1694, 1595, 1489 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.85–7.83 (m, 2 H, ArH), 7.44–
7.26 (m, 3 H, ArH), 7.16–7.12 (m, 1 H, ArH), 6.42–6.37 (m, 2 H,
ArH), 4.93–4.80 (m, 2 H, H-5, NH), 3.15 (dd, J = 8.8, 16.5 Hz, 1 H,
H-4a), 3.00 (dd, J = 7.4, 16.6 Hz, 1 H, H-4b).
13C NMR (100 MHz, CDCl3): d = 170.5, 143.0, 138.7, 128.8, 124.5,
118.5, 110.6, 108.4, 52.4, 39.4.
MS (ESI+): m/z (%) = 213 (76.8, [M + Na]+), 191 (25.1, [M + H]+),
189 (100, [M – H]+).
Anal. Calcd for C11H14N2O: C, 69.45; H, 7.42; N, 14.73. Found: C,
69.58; H, 7.37; N, 14.77.
MS (ESI+): m/z (%) = 251 (100, [M + Na]+), 229 (48.6, [M + H]+),
227 (19.2, [M – H]+).
5-(4-Chlorophenyl)-2-p-tolylpyrazolidin-3-one (4bc)
White powder; mp 92–95 °C.
Anal. Calcd for C13H12N2O2: C, 68.41; H, 5.30; N, 12.27. Found: C,
68.62; H, 5.22; N, 12.21.
IR (KBr): 3413, 3132, 1674, 1619, 1509, 1400 cm– 1
.
2,5-Diphenylpyrazolidin-3-one (4af)
Viscous oil.
IR (KBr): 3212, 3063, 2927, 1695, 1596, 1495 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.87–7.85 (m, 2 H, ArH), 7.35–
7.30 (m, 7 H, ArH), 7.10–7.08 (m, 1 H, ArH), 4.85 (br, 1 H, NH),
4.69–4.64 (m, 1 H, H-5), 3.00 (dd, J = 7.2, 16.4 Hz, 1 H, H-4a),
2.85 (dd, J = 8.4, 16.4 Hz, 1 H, H-4b).
1H NMR (400 MHz, CDCl3): d = 7.75–7.73 (m, 2 H, ArH), 7.40–
7.31 (m, 4 H, ArH), 7.15 (d, J = 8.3 Hz, 2 H, ArH), 4.89 (br d,
J = 6.8 Hz, 1 H, NH), 4.77–4.73 (m, 1 H, H-5), 3.14 (dd, J = 7.6,
16.3 Hz, 1 H, H-4a), 2.86 (dd, J = 7.4, 16.3 Hz, 1 H, H-4b), 2.32 (s,
3 H, CH3).
13C NMR (100 MHz, CDCl3): d = 170.3, 136.1, 134.2, 129.9, 129.4,
129.3, 129.1, 127.8, 118.4, 56.9, 41.6, 20.9.
13C NMR (100 MHz, CDCl3): d = 171.1, 138.8, 128.9, 128.8, 128.3,
126.5, 124.3, 118.3, 118.2, 57.6, 41.5.
MS (ESI+): m/z (%) = 309 (33.9, [M(35Cl) + Na]+), 287 (47.2,
[M(35Cl) + H]+ or [M(37Cl) – H]+), 285 (100, [M(35Cl) – H]+).
MS (ESI+): m/z (%) = 238 (18.1, [M]+), 237 (100, [M – H]+).
Anal. Calcd for C16H15ClN2O: C, 67.02; H, 5.27; N, 9.77. Found: C,
66.87; H, 5.32; N, 9.81.
Anal. Calcd for C15H14N2O: C, 75.61; H, 5.92; N, 11.76. Found: C,
75.37; H, 5.94; N, 11.70.
5-(4-Methoxyphenyl)-2-p-tolylpyrazolidin-3-one (4ba)
Light brown powder; mp 89–91 °C.
IR (KBr): 3475, 3414, 3128, 1685, 1615, 1400 cm–1.
2,5-Di(p-tolyl)pyrazolidin-3-one (4bb)
Light brown powder; mp 78–80 °C.
IR (KBr): 3128, 1687, 1509, 1400 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.74 (d, J = 8.5 Hz, 2 H, ArH),
7.32 (d, J = 8.6 Hz, 2 H, ArH), 7.14 (d, J = 8.3 Hz, 2 H, ArH), 6.90
(d, J = 8.8 Hz, 2 H, ArH), 4.72 (br, 2 H, H-5, NH), 3.80 (s, 3 H,
CH3), 3.01–2.95 (m, 2 H, H-4), 2.31 (s, 3 H, CH3).
13C NMR (100 MHz, CDCl3): d = 170.8, 159.6, 136.3, 133.9,
129.28, 129.26, 127.8, 118.4, 114.3, 57.5, 55.3, 41.4, 20.9.
1H NMR (400 MHz, CDCl3): d = 7.76 (d, J = 8.0 Hz, 2 H, ArH),
7.30 (d, J = 8.0 Hz, 2 H, ArH), 7.20–7.14 (m, 4 H, ArH), 4.75 (br,
2 H, H-5, NH), 3.08–3.04 (m, 1 H, H-4a), 2.97 (dd, J = 8.0, 16.0 Hz,
1 H, H-4b), 2.35 (s, 3 H, CH3), 2.32 (s, 3 H, CH3).
13C NMR (100 MHz, CDCl3): d = 170.7, 138.2, 136.3, 134.0, 129.6,
129.3, 126.5, 118.4, 57.5, 41.5, 21.1, 20.8.
MS (ESI+): m/z (%) = 305 (100, [M + Na]+), 283 (65.3, [M + H]+).
MS (ESI+): m/z (%) = 289 (100, [M + Na]+), 267 (50.5, [M + H]+),
Anal. Calcd for C17H18N2O2: C, 72.32; H, 6.43; N, 9.92. Found: C,
72.21; H, 6.47; N, 9.89.
265 (13.9, [M – H]+).
Anal. Calcd for C17H18N2O: C, 76.66; H, 6.81; N, 10.52. Found: C,
76.85; H, 6.77; N, 10.42.
2-(4-Chlorophenyl)-5-methylpyrazolidin-3-one (4cd)
Light brown powder; mp 103–104 °C.
5-Phenyl-2-p-tolylpyrazolidin-3-one (4bf)
IR (KBr): 3130, 2930, 1692, 1492, 1400 cm–1.
Viscous oil.
1H NMR (400 MHz, CDCl3): d = 7.81 (d, J = 8.5 Hz, 2 H, ArH),
7.29 (d, J = 8.5 Hz, 2 H, ArH), 4.45 (br, s, 1 H, NH), 3.82-3.75 (m,
1 H, H-5), 2.84 (dd, J = 6.4, 16.4 Hz, 1 H, H-4a), 2.46 (dd, J = 8.4,
16.4 Hz, 1 H, H-4b), 1.34 (d, J = 6.3 Hz, 3 H, CH3).
13C NMR (100 MHz, CDCl3): d = 172.1, 137.6, 129.1, 128.7, 119.4,
51.1, 42.6, 18.5.
IR (KBr): 3217, 3031, 2922, 2856, 1682, 1614, 1510 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.76 (d, J = 8.4 Hz, 2 H, ArH),
7.45–7.33 (m, 5 H, ArH), 7.15 (d, J = 8.4 Hz, 2 H, ArH), 4.80–4.76
(m, 2 H, H-5, NH), 3.11 (dd, J = 7.2, 16.0 Hz, 1 H, H-4a), 2.96 (dd,
J = 8.4, 16.4 Hz, 1 H, H-4b), 2.32 (s, 3 H, CH3).
Synthesis 2008, No. 20, 3223–3228 © Thieme Stuttgart · New York