CH2C(Ph)=N-OCOCH2Me], 2.23 (s, 3H, pyrazole 5-Me), 2.22−2.28 [m, 2H, CH2C(Ph)=N-OCOCH2Me],
3.30 [AB q, J = 13.4 Hz, 2H, CH2C(Ph)=N-OCOCH2Me], 4.39 (s, 1H, OH), 7.12−7.15 (m, 1H, Ph-H),
7.26−7.32 (m, 7H, Ph-H), 7.60−7.62 (m, 2H, Ph-H); 13C NMR (CDCl3):
δ
8.60
[CH2C(Ph)=N-OCOCH2Me], 13.6 (pyrazole 5-Me), 26.1 [CH2C(Ph)=N-OCOCH2Me], 40.8
[CH2C(Ph)=N-OCOCH2Me], 78.2 (pyrazole C-4), 118.7, 125.2, 127.8, 128.3, 128.6, 130.3, 131.1, 137.4
(Ph-C), 160.6 [CH2C(Ph)=N-OCOCH2Me], 161.0 (pyrazole C-5), 171.4 [CH2C(Ph)=N-OCOCH2Me],
171.8 (pyrazole C-3); MS: m/z 380 [M+H]+. Anal. Calcd for C21H21N3O4: C, 66.48; H, 5.58; N, 11.08.
Found: C, 66.47; H, 5.65; N, 11.09.
(E)-4-[2-[(Benzoyloxy)imino]-2-phenylethyl]-2,4-dihydro-4-hydroxy-5-methyl-2-phenyl-3H-pyrazol-
3-one (9c): Colorless needles (0.121 g, 28%), mp 160−162 °C (acetone/petroleum ether); IR (KBr): ν
3375 (OH), 1727 cm-1 (CO); 1H NMR (CDCl3): δ 2.06 (s, 3H, pyrazole 5-Me), 3.57 [AB q, J = 13.4 Hz,
2H, CH2C(Ph)=N-OCOPh], 3.61 (s, 1H, OH), 7.11−7.14 (m, 1H, Ph-H), 7.25−7.39 (m, 7H, Ph-H),
7.51−7.60 (m, 3H, Ph-H), 7.72−7.73 (m, 2H, Ph-H), 8.00−8.02 (m, 2H, Ph-H); 13C NMR (CDCl3): δ 13.3
(pyrazole 5-Me), 34.8 [CH2C(Ph)=N-OCOPh], 78.5 (pyrazole C-4), 118.5, 125.4, 128.0, 128.4, 128.6,
128.7, 129.7, 131.0, 133.50, 133.53, 137.2 (Ph-C), 161.21 (pyrazole C-5), 161.23 [CH2C(Ph)=N-OCOPh],
163.3 [CH2C(Ph)=N-OCOPh], 172.2 (pyrazole C-3); MS: m/z 427 [M+]. Anal. Calcd for C25H21N3O4: C,
70.25; H, 4.95; N, 9.83. Found: C, 70.26; H, 5.05; N, 9.83.
(Z)-4-[2-[(Benzoyloxy)imino]-2-phenylethyl]-2,4-dihydro-4-hydroxy-5-methyl-2-phenyl-3H-pyrazol-
3-one (9c): Pale yellow solid (0.177 g, 41%), mp 39−41 °C (Et2O/petroleum ether); IR (KBr): ν 3392
(OH), 1747, 1723 cm-1 (CO); 1H NMR (CDCl3): δ 2.30 (s, 3H, pyrazole 5-Me), 3.40 [AB q, J = 14.6 Hz,
2H, CH2C(Ph)=N-OCOPh], 4.69 (br, 1H, OH), 7.11−7.14 (m, 1H, Ph-H), 7.25−7.37 (m, 9H, Ph-H),
7.48−7.52 (m, 1H, Ph-H), 7.58−7.61 (m, 2H, Ph-H), 7.77−7.79 (m, 2H, Ph-H); 13C NMR (CDCl3): δ 13.7
(pyrazole 5-Me), 41.0 [CH2C(Ph)=N-OCOPh], 78.4 (pyrazole C-4), 118.7, 125.2, 127.8, 128.29, 128.32,
128.5, 128.6, 129.67, 129.71, 130.4, 131.2, 133.4, 137.3 (Ph-C), 161.2 (pyrazole C-5), 161.5
[CH2C(Ph)=N-OCOPh], 163.3 [CH2C(Ph)=N-OCOPh], 171.9 (pyrazole C-3); MS: m/z 428 [M+H]+. Anal.
Calcd for C25H21N3O4 0.5H2O: C, 68.80; H, 5.08; N, 9.63. Found: C, 68.81; H, 5.03; N, 9.42.
(E)-2,4-Dihydro-4-hydroxy-5-methyl-4-[2-[[(4-nitrobenzoyl)oxy]imino]-2-phenylethyl]-2-phenyl-3H-
pyrazol-3-one (9d): Yellow needles (0.079 g, 17%), mp 177−179 °C (acetone/petroleum ether); IR
(KBr): ν 3404 (OH), 1739, 1719, 1703 cm-1 (CO); 1H NMR (CDCl3): δ 2.03 (s, 3H, pyrazole 5-Me), 3.53
[AB q, J = 13.7 Hz, 2H, CH2C(Ph)=N-OCO-4-NO2-C6H4], 3.65 (s, 1H, OH), 7.10−7.13 (m, 1H, Ph-H),
7.23−7.27 (m, 2H, Ph-H), 7.37−7.46 (m, 3H, Ph-H), 7.58−7.60 (m, 2H, Ph-H), 7.75−7.78 (m, 2H, Ph-H),
8.06−8.10 (m, 4H, Ph-H); 13C NMR (CDCl3):
[CH2C(Ph)=N-OCO-4-NO2-C6H4], 78.4 (pyrazole C-4), 118.2, 123.6, 125.5, 128.0, 128.8, 130.8, 131.4,
δ
13.2 (pyrazole 5-Me), 35.2