Jan-Feb 2007
A Facile Preparation of Selenohydantoins Using Isoselenocyanates
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(3H, m, Ar), 9.00 (1H, br, NH), 13C nmr (125 MHz, DMSO-d6):
ꢀ 36.9, 62.0, 127.9, 128.3, 129.1, 129.4, 129.5, 133.0, 133.6,
173.8, 183.6, 77Se nmr (95 MHz, DMSO-d6): ꢀ 286.2, ms (CI):
m/z = 331 [M++1]. Anal. Calcd. for C16H13N2OSe: C, 58.55; H,
3.99; N, 8.53. Found: C, 58.51; H, 4.18; N, 8.61.
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3-Phenyl-2-selenoxoimidazolidin-4-one (3e). White crystals;
1
mp 230 ºC, ir (potassium bromide): 3125, 1764, 1512 cm-1. H
nmr (500 MHz, DMSO-d6): ꢀ 4.18 (2H, s, CH2), 7.28-7.51 (5H,
m, Ar), 11.1 (1H, br, NH), 13C nmr (125 MHz, DMSO-d6): ꢀ
50.9, 129.2, 129.6, 134.7, 134.7, 172.5, 183.7, 77Se nmr (95
MHz, DMSO-d6): ꢀ 254.9, ms (CI): m/z = 241 [M++1]. Anal.
Calcd. for C9H7N2OSe: C, 45.40; H, 2.96; N, 11.76. Found: C,
45.57; H, 2.82; N, 11.51.
N-Phenyl-N'-[(methoxycarbonyl)methyl]selenourea (4).
Yellow oil, ir (nujol): 3368, 3150, 2986, 1538 cm-1, 1H nmr (500
MHz, CDCl3): ꢀ 3.75 (3H, s, CH3), 4.51 (2H, d, J =4.6 Hz, CH2),
6.98 (1H, br, NH), 7.27-7.35 (3H, m, Ar), 7.42-7.47 (2H, m, Ar),
9.09 (1H, br, NH), 13C nmr (125 MHz, CDCl3): ꢀ 49.0, 52.5,
124.8, 127.6, 130.1, 135.6, 169.8, 178.8, 77Se nmr (95 MHz,
CDCl3): ꢀ 229.5, ms (CI): m/z = 273 [M++1]. Anal. Calcd. for
C10H12N2O2Se: C, 44.29; H, 4.46; N, 10.33. Found: C, 44.14; H,
4.47; N, 10.34.
Acknowledgment. This work was supported by a Grant-in-
Aid for Science Research from the Ministry of Education,
Culture, Sports, Science and Technology of Japan (No.
15550030 and 17550099) to which we are grateful.
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