Synthesis of 5,5-Diphenylhydantoin Derivatives
NH); 13C NMR (DMSO, 125 MHz) δ: 24.15 (2CH3),
75.27 (C), 128.10 (2C), 128.98 (4CH), 130.87 (4CH),
135.22 (2C), 157.23 (CO), 174.31 (CO); IR (KBr) v:
3020, 3360 (s, NH), 1650, 1800 (s, C=O), 1400—1520
11.02 (s, NH); 13C NMR (DMSO, 125 MHz) δ: 55.61
(CH3), 73.23 (C), 114.19 (2CH), 127.14 (2CH), 127.30
(2CH), 128.86 (2CH), 128.92 (CH), 132.33 (C), 140.36
(C), 156.38 (C), 159.31 (C), 175.52 (C); IR (KBr) v:
3000, 3400 (s, NH), 1670, 1810 (s, C=O), 1380—1520
-1
(m,+C=C), 760 (m, CH) cm ; MS (70 eV) m/z: 280
-1
(M ), 251, 237, 208, 180, 118, 104, 91, 77.
(m,+C=C), 700 (m, CH) cm ; MS (70 eV) m/z: 282
5,5-Bis(3-methylphenyl)hydantoin (2c)
UV
(M ), 253, 239, 210, 180, 134, 107, 104, 77.
(CH3OH) λmax: 236 nm; 1H NMR (DMSO, 500 MHz) δ:
3.6 (s, 6H), 6.80—7.22 (m, 8H), 9.20 (s, NH), 11.00 (s,
NH); 13C NMR (DMSO, 125 MHz) δ: 22.43 (2CH3),
78.17 (C), 124.56 (2CH), 127.35 (2CH), 128.14 (2CH),
129.06 (2CH), 134.39 (2C), 137.73 (2C), 156.48 (CO),
174.22 (CO); IR (KBr) v: 3020, 3340 (s, NH), 1650,
1760 (s, C=O), 1460—1520 (m, C=C), 780 (m, CH)
5-(4-Dimethylaminophenyl)-5-phenylhydantoin
1
(2i) UV (CH3OH) λmax: 235 nm; H NMR (DMSO,
500 MHz) δ: 3.51 (s, 6H), 6.74—7.47 (m, 9H), 9.00 (s,
NH), 10.78 (s, NH); 13C NMR (DMSO, 125 MHz) δ:
43.26 (2CH3), 77.63 (C), 112.48 (2CH), 113.72 (C),
127.46 (2CH), 127.79 (2CH), 128.04 (CH), 128.59
(2CH), 135.61 (C), 140.31 (C), 151.22 (C), 156.47 (C),
175.81 (C); IR (KBr) v: 3120, 3340 (s, NH), 1650, 17-90
+
-1
cm ; MS (70 eV) m/z: 280 (M ), 251, 237, 208, 180,
1
118, 104, 91, 77.
(s, C=O), 1390—1510 (m, C=C), 700 (m, CH) cm ;
5,5-Bis(4-chlorophenyl)hydantoin (2d)
UV
MS (70 eV) m/z: 295 (M+), 266, 252, 223, 180, 147,
120, 104, 77.
(CH3OH) λmax: 234 nm; 1H NMR (DMSO, 500 MHz) δ:
7.12—7.24 (m, 8H), 9.40 (s, NH), 11.12 (s, NH);
13C NMR (DMSO, 125 MHz) δ: 77.29 (C), 125.86
(4CH), 127.34 (2C), 129.68 (4CH), 132.55 (2C), 155.96
(C), 174.09 (C); IR (KBr) v: 3000, 3300 (s, NH), 1670,
1790 (s, C=O), 1400—1500 (m, C=C), 770 (m, CH)
5-(4-Methoxyphenyl)-5-(3-bromophenyl)hydantoin
1
(2j) UV (CH3OH) λmax: 232 nm; H NMR (DMSO,
500 MHz) δ: 3.63 (s, 3H), 6.96—7.55 (m, 8H), 9.30 (s,
NH), 11.16 (s, NH); 13C NMR (DMSO, 125 MHz) δ:
55.61 (CH3), 76.24 (C), 114.37 (2CH), 122.18 (C),
126.08 (CH), 128.21 (2CH), 129.65 (CH), 131.14 (CH),
131.37 (CH), 131.90 (C), 143.00 (C), 156.24 (C),
159.47 (C), 174.99 (C); IR (KBr) v: 3000, 3380 (s, NH),
1670, 1790 (s, C=O), 1380—1520 (m, C=C), 840 (m,
+
-1
cm ; MS (70 eV) m/z: 320 (M ), 291, 277, 248, 215,
180, 138, 111, 104, 77.
5,5-Bis(3-nitrophenyl)hydantoin
(2e)
UV
(CH3OH) λmax: 242 nm; 1H NMR (DMSO, 500 MHz) δ:
7.40—8.51 (m, 8H), 8.90 (s, NH), 11.85 (s, NH);
13C NMR (DMSO, 125 MHz) δ: 75.68 (C), 119.17
(2CH), 124.87 (2CH), 130.46 (2CH), 131.79 (2C),
131.96 (2CH), 150.15 (2C), 156.90 (CO), 176.23 (CO);
IR (KBr) v: 2900, 3500 (s, NH), 1660, 1750 (s, C=O),
1520—1550 (m, C=C), 1430, 1500 (+s, N=O), 760 (m,
+
-1
CH) cm ; MS (70 eV) m/z: 360 (M ), 331, 317, 288,
258, 210, 182, 180, 155, 134, 107, 104, 77.
Conclusion
In conclusion, to obtain a rapid, efficient and
“green” synthesis of 5,5-diphenylhydantoin derivatives,
ultrasound irradiation has been applied to the reaction
mixtures containing symmetrical or unsymmetrical ben-
zil derivatives and urea, which allowed us to achieve
5,5-diphenylhydantoin derivatives in a good yield and
short time without any side product. This convenient
procedure will allow a further increase of the diversity
within the hydantoin family.
-1
CH) cm ; MS (70 eV) m/z: 342 (M ), 313, 299, 270,
225, 180, 149, 122, 104, 77.
5,5-Bis(2-nitrophenyl)hydantoin
(2f)
UV
(CH3OH) λmax: 240 nm; 1H NMR (DMSO, 500 MHz) δ:
7.52—8.10 (m, 8H), 9.20 (s, NH), 11.70 (s, NH);
13C NMR (DMSO, 125 MHz) δ: 76.85 (C), 123.01
(2CH), 123.58 (2CH), 127.65 (2CH), 131.52 (2CH),
131.69 (2C), 150.07 (2C), 156.49 (CO), 173.72 (CO);
IR (KBr) v: 3000, 3200 (s, NH), 1650, 1700 (s, C=O),
1490—1520 (m, C=C), 1400—1450 +(s, N=O), 770 (m,
Acknowledgements
-1
CH) cm ; MS (70 eV) m/z: 342 (M ), 313, 299, 270,
We are grateful to the University of Kashan for the
partial support to this work.
180, 149, 122, 104, 77.
5-(4-Methylphenyl)-5-phenylhydantoin (2g) UV
(CH3OH) λmax: 232 nm; 1H NMR (DMSO, 500 MHz) δ:
2.58 (s, 3H), 7.00—7.40 (m, 9H), 9.40 (s, NH), 10.84 (s,
NH); 13C NMR (DMSO, 125 MHz) δ: 25.07 (CH3),
76.98 (C), 126.45 (C), 127.37 (2CH), 127.86 (2CH),
128.09 (CH), 128.62 (2CH), 129.84 (2CH), 131.20 (C),
136.96 (C), 153.94 (C), 175.77 (C); IR (KBr) v: 3020,
3300 (s, NH), 1660, 1750 (s, C=O), 1400—1460 (+m,
References
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5
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-1
C=C), 760 (m, CH) cm ; MS (70 eV) m/z: 266 (M ),
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(2h)
1
UV (CH3OH) λmax: 234 nm; H NMR (DMSO, 500
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