El Ashry et al.
12
7.34–7.85 (10H, Ar-H). 13C NMR (CDCl3): dc ¼ 48.2 (C-3), 54.6 (C-1), 68.2 (C-2),
111.6, 115.8, 124.2, 124.7, 128.7, 129.8, 130.2, 130.9, 132.9, 133.6, 139.6
(C-aromatic), 147.3 (CH2O), (C-N), 154.2 (C55N). Anal. Calcd for C21H18N4O3
(374.39): C, 67.37; H, 4.85; N, 14.86. Found: C, 67.05; H, 4.60; N, 14.59. Data of 24
1H NMR (500 MHz, DMSO-d6): d ¼ 1.98 (s, 3H, CH3CO), 3.71 (dd, 1H,
J3 ,2 ¼ 5.3 Hz, J3 ,3 ¼ 10.7 Hz, H-300), 3.81 (dd, 1H,, J3,2 ¼ 4.6 Hz, J3 ,3 ¼ 10.7 Hz,
0
00
0
0
00
H-30), 4.12–4.18 (m, 1H, H-20), 4.39 (ddd, 2H, J1 ,1 ¼ 9.2 Hz, J1 ,2 ¼ 4.6 Hz,
0
00
0
0
J1 ,2 ¼ 4.9 Hz, H-10, H-100), 5.15 (s, 2H, CH2-O), 7.35–7.85 (m, d, 10H, Ar-H). 13C
NMR (CDCl3): dc ¼ 20.9 (CH3CO), 48.2 (C-30), 54.6 (C-10), 68.2 (C-20), 111.9, 115.8,
124.2, 125.4, 129.4, 130.0, 130.2, 131.0, 132.9, 133.7, 138.8, 139.2 (C-aromatic),
147.4 (CH2O), 154.2 (C55N), 170.7 (C55O). Anal. Calcd for C23H20N4O4 (416.42):
C, 66.34; H, 4.84; N, 13.45. Found: C, 66.07; H, 4.65; N, 13.19.
00
0
3-[5-(Acetoxymethyl)-1-phenyl-pyrazol-3-yl]-1-(2,3-
dihydroxypropyl)-quinoxalin-2-one (24)
Method A. A mixture of 17 (0.2 g, 0.6 mmol) and potassium carbonate
(0.1 g, 0.7 mmol) in DMF was heated for 1 h, the epichlorohydrin (0.08 mL,
0.8 mmol) was added, and the reaction mixture was stirred at rt for 3 h, and
then the mixture was poured onto ice water. After successive washing with
water, the precipitate was recrystallized from ethanol to give 24 in 60%
yield, which could be also given under the same conditions by using microwave
irradiation for 6 min.
Method B. A suspension of 23 (0.14 mmol) in distilled water (3 mL) and a
drop of HCl was refluxed for 4 h, and then the solvent was evaporated under
reduced pressure. The residue was extracted with chloroform and crystallized
1
from ethanol to give compound 24 as colorless crystals. Rf 0.27 (H/E 1/2). H
NMR (500 MHz, DMSO-d6): d ¼ 1.98 (s, 3H, CH3CO), 3.48 (q, 2H,
J3,2 ¼ 5.3 Hz, J3,3 ¼ 10.7 Hz, J3 ,2 ¼ 5.3 Hz, J3 ,3 ¼ 10.7 Hz, H-30, H-300),
3.93–3.94 (m, 1H, H-20), 4.35 (dd, 2H, Jcis ¼ 4.6 Hz, J gem ¼ 8.4 Hz, H-10,
H-100), 4.81 (dd, 1H, J ¼ 5.3 Hz, J ¼ 6.1 Hz, OH, D2O exchangeable), 4.96
(d, 1H, J ¼ 5.3 Hz, OH, D2O exchangeable), 5.15 ( s, 2H, CH2-O), 7.34–7.98
0
00
0
00
0
13
(m, d, 10H, Ar-H). C NMR (CDCl3): dc ¼ 21.0 (CH3CO), 56.7 (C-10), 64.6
(C-30), 69.4 (C-20), 113.0, 116.0, 124.0, 125.4, 129.3, 130.0, 130.2, 130.8, 133.0,
138.7, 139.3 (C-aromatic), 147.6 (CH2O), 147.7 (C-N), 154.2 (C55N), 170.4
(CO). Anal. Calcd for C23H22N4O5 (434.44): C, 63.59; H, 5.10; N, 12.90.
Found: C, 63.61; H, 4.82; N, 13.05.
3-[5-(Acetoxymethyl)-1-phenyl-pyrazol-3-yl]-1-(2,3-di-O-
acetoxy-propyl)-quinoxalin-2-one (25)
A solution of 24 (0.2 g, 0.46 mmol) in pyridine (2 mL) and acetic anhydride
(2 mL) was irradiated for 3 min, then poured onto ice water. The product that