G Model
CRAS2C-3784; No. of Pages 7
6
J. Safari, L. Javadian / C. R. Chimie xxx (2013) xxx–xxx
4.88, N 13.58, O 23.28; found: C 58.27, H 4.84, N 13.61, O
23.27.
(C5O), 67.16 (Cspiro), 46.67 (C–H), 23.99 (C–H), 22.17 (C–
H), 20.92 (C–H).; IR (KBr cmꢀ1
: 3197 (N–H, s), 3117 (N–
) n
¯
H, s), 2981 (C–H), 2971 (C–H), 1771 (C5O), 1720 (C5O)
and 1403 (N–H, b). Anal. calcd. for C8H14N2O2 (170.177): C
56.46, H 8.28, N 16.46, O 18.80; found: C 56.47, H 8.27, N
16.48, O 18.82.
4.4.4. 5-(2-Methoxyphenyl)-imidazolidine-2,4-dione
(C10H10N2O3, 4d)
White needles; UV (CH3OH)
(DMSO-d6, 400 MHz) : 9.40 (s, 1H, N3–H), 7.99 (s, 1H, N1–
l
max: 274 nm; 1H NMR
d
H), 7.30 (d, J = 7.00 Hz, 1H), 7.08–6.92 (m, 2H), 6.85 (d,
J = 7.00 Hz, 1H), 4.85 (s, 1H) and 4.01 (s, 3H); 13C NMR
4.4.9. 1,3-Diazaspiro[4,5]decane-2,4-dione (C8H12N2O2, 4i)
White needles; UV (CH3OH)
(DMSO-d6, 400 MHz) : 10.47 (s, 1H, N3–H), 8.38 (s, 1H,
N1–H), 1.62–1.45 (m, 9H) and 1.21–1.27 (m, 1H).; 13C NMR
(DMSO-d6, 100 MHz) : 179.61 (C5O), 157.51 (C5O),
62.89 (Cspiro), 39.76 (2CH2), 25.33 (2CH2), 21.71 (CH2).; IR
(KBr cmꢀ1
: 3250 (N–H), 3199 (N–H, s), 3069 (5C–H, s),
l
max: 348 nm; 1H NMR
(DMSO-d6, 100 MHz)
157.62 (C), 128.13 (2CH), 119.11 (2CH), 114.02 (C), 62.01
(Cspiro), 54.17 (C–H); IR (KBr cmꢀ1
: 3348 (N–H, m), 3217
d
: 166.01 (C5O), 161.12 (C5O),
d
)
n
¯
d
(N–H, s), 1780 (C5O, s), 1729 (C5O, s), 1612 (C5C, w),
1518 (C5C, w) and 1250 (C–O, m). Anal. calcd. for
)
n
¯
C
10H10N2O3 (206.166): C 58.25,
H
4.88, N 13.58,
O
2936 (C–H, s), 1776 (C5O, m), 1734 (C5O, s), 1456 (N–H, b,
s), 1411 (s), 1292 (m), 1228 (m), 1072 (m), 942 (m), 780
(m) and 753 (m). Anal. calcd. for C8H12N2O2 (168.106): C
57.15, H 7.18, N 16.66, O 19.03; found: C 57.17, H 7.19, N
16.64, O 19.01.
23.28; found: C 58.22, H 4.90, N 13.65, O 23.30.
4.4.5. 5-(2-Chlorophenyl)-imidazolidine-2,4-dione
(C9H7N2O2Cl, 4e)
White needles; UV (CH3OH)
(DMSO-d6, 400 MHz) : 9.70 (s, 1H, N3–H), 8.03 (s, 1H, N1–
l
max: 275 nm; 1H NMR
d
4.4.10. 5-Methyl-5-phenyl-imidazolidine-2,4-dione
H), 7.90 (d, J = 6.98 Hz, 1H), 7.71 (t, J = 6.98 Hz, 1H), 7.35–
7.36 (m, 2H) and 5.13 (s, 1H); 13C NMR (DMSO-d6,
(C10H10N2O2, 4j)
White needles; UV (CH3OH)
(DMSO-d6, 400 MHz) : 10.75(s, 1H, N3–H), 8.62 (s, 1H, N1–
H), 7.47–7.45 (d, J = 6 Hz, 2H), 7.40–7.36 (t, J = 6 Hz, 2H),
7.32–7.31 (t, J = 6 Hz, 1H) and 1.64 (s, 3H); 13C NMR
l
max: 252 nm; 1H NMR
100 MHz)
127.12 (2CH), 120.03 (2CH), 113.63 (C), 61.04 (Cspiro); IR
(KBr cmꢀ1
: 3350 (N–H, m), 3215 (N–H, s), 1779 (C5O, s),
d
: 168.71 (C5O), 151.04 (C5O), 158.37 (C),
d
)
n
¯
1732 (C5O, s), 1613 (C5C, w) and 1514 (C5C, w). Anal.
calcd. for C9H7N2O2 Cl (210.450): C 51.33, H 3.33, N 13.30,
O 15.22; Cl 16.82; found: C 51.29, H 3.35, N 13.35, O 15.24.
(DMSO-d6, 100 MHz)
127.41 (C), 127.38 (2CH), 126.79 (2CH), 123.70 (2CH),
71.22 (Cspiro), 22.14 (C–H); IR (KBr cmꢀ1
: 3282 (N–H,s),
d: 166.16 (C5O), 157.41 (C5O),
)
n
¯
3208 (N–H, s), 3064 (5C–H,m), 2989 (C–H, m), 1731 (C5O,
s), 1726 (C5O, s) and 787 (5C–H, b). Anal. calcd. for
C10H10N2O2 (190.167): C 63.16, H 5.29, N 14.73, O 16.82;
4.4.6. 5-n-Butyl-imidazolidine-2,4-dione (C7H12N2O2, 4f)
White needles; UV (CH3OH)
l
max: 319 nm; 1H NMR
(DMSO-d6, 400 MHz) : 10.52(s, 1H, N3–H), 7.89(s, 1H, N1–
d
found: C 63.17, H 5.27, N 14.74, O 16.80.
H), 1.49–1.52 (t, J = 5 Hz, 2H), 1.55–1.57 (m, 2H), 0.91–0.93
(m, J = 5 Hz, 2H) and 0.81–0.79 (t, J = 5 Hz, 3H); 13C NMR
4.4.11. 5-Methyl-5-(4-chloro phenyl)-imidazolidine-2,
(DMSO-d6, 100 MHz)
(C), 46.73 (C–H), 23.87 (C–H), 22.23 (C–H), 20.85 (C–H).; IR
(KBr cmꢀ1
: 3201 (N–H, s), 3189 (N–H, s), 2899 (C–H),
2875 (C–H), 1775 (C5O), 1730 (C5O) and 1437 (N–H, b).
Anal. calcd. for C7H12N2O2 (156.090): C 53.85, H 7.68, N
17.95, O 20.52; found: C 53.87, H 7.69, N 17.93, O 20.51.
d
: 166.51 (C5O), 158.50 (C5O), 67.21
4-dione (C10H9ClN2O2, 4k)
White needles; UV (CH3OH)
(DMSO-d6, 400 MHz) : 10.6 (s, 1H, N3–H), 8.64 (s, 1H,
N1–H), 7.49 (d, J = 8.3, 2H), 7.47 (d, J = 8.3, 2H) and 1.63 (s,
3H); 13C NMR (DMSO-d6, 100 MHz)
: 177.14 (C5O),
156.69 (C5O), 139.39 (C), 133.16 (C), 128.89 (2CH),
127.77 (2CH), 64.06 (Cspiro), 25.51 (CH3); IR (KBr cmꢀ1
) n:
¯
l
max: 272 nm; 1H NMR
)
n
¯
d
d
4.4.7. 5-Isobutyl-imidazolidine-2,4-dione (C7H12N2O2, 4g)
3274 (N–H, s), 3209(N–H, s), 1778 (C5O, m), 1725 (C5O,
s), 1489 (C5C, w), 1447 (C5C, w), and 1401 (N–H, b, m).
Anal. calcd. for C10H9ClN2O2 (224.624): C 53.47, H 4.03, N
12.47, O 14.24, Cl 15.78; found: C 53.46, H 4.04, N 12.49,
O 14.27, Cl 15.80.
White needles; UV (CH3OH)
(DMSO-d6, 400 MHz) : 10.43 (s, 1H, N3–H), 7.74 (s, 1H, N1–
l
max: 321 nm; 1H NMR
d
H), 1.49–1.53 (m, 2H), 1.43–1.49 (m, 1H), 0.88–0.89 (d,
J = 5 Hz, 3H) and 0.81–0.79 (d, J = 5 Hz, 3H); 13C NMR
(DMSO-d6, 100 MHz)
(C), 46.72 (C–H), 23.92 (C–H), 22.19 (C–H), 20.97 (C–H).; IR
(KBr cmꢀ1
: 3204 (N–H, s), 3212 (N–H, s), 2975 (C–H),
2978 (C–H), 1774 (C5O), 1722 (C5O) and 1411 (N–H, b).
Anal. calcd. for C7H12N2O2 (156.090): C 53.85, H 7.68, N
17.95, O 20.52; found: C 53.86, H 7.69, N 17.94, O 20.51.
d: 166.51 (C5O), 158.53 (C5O), 67.20
4.4.12. 5-Methyl-5-(3-methyl phenyl)-imidazolidine-2,4-
)
n
¯
dione (C11H12N2O2, 4l)
White powder; UV (CH3OH)
(DMSO-d6, 400 MHz) : 10.73 (s, 1H, N3–H), 8.56 (s, 1H, N1–
H), 7.42–7.25 (s, 3H), 7.12 (s, 1H), 2.30 (s, 3H) and 1.87–
1.61 (s, 3H); 13C NMR (DMSO-d6, 100 MHz)
: 166.16
l
max: 268 nm; 1H NMR
d
d
4.4.8. 5-Isobutyl-5-methyl-imidazolidine-2,4-dione
(C5O), 157.41 (C5O), 137.99 (C), 131.30 (CH), 128.16 (CH),
(C8H14N2O2, 4h)
127.31 (CH), 126.73 (CH), 123.32 (C), 72.43 (Cspiro), 22.14
White needles; UV (CH3OH)
l
max: 312 nm; 1H NMR
(CH3), 20.84 (CH3); IR (KBr cmꢀ1
) n: 3290 (N–H, s), 3211
¯
(DMSO-d6, 400 MHz) : 10.52(s, 1H, N3–H), 7.89(s, 1H, N1–
H), 1.57–1.51 (m, 2H), 1.46–1.42 (m, 1H), 1.20 (s, 3H),
d
(N–H, s), 3050 (5C–H, m), 2972 (C–H, m), 1798 (C5O, m),
1730 (C5O, s), 1018 (m), and 762 (5C–H, b). Anal. calcd. for
0.87–0.86 (d, J = 5 Hz, 3H) and 0.79–0.77 (d, J = 5 Hz, 3H);
13C NMR (DMSO-d6, 100 MHz)
d: 166.46 (C5O), 158.47
C
11H12N2O2 (204.194): C 64.70, H 5.91, N 13.71, O 15.67;
found: C 64.72, H 5.94, N 13.69, O 15.65.
Please cite this article in press as: Safari J, Javadian L. A one-pot synthesis of 5,5-disubstituted hydantoin derivatives
using magnetic Fe3O4 nanoparticles as a reusable heterogeneous catalyst. C. R. Chimie (2013), http://dx.doi.org/