RSC Advances
Paper
128.30, 129.51, 129.62, 138.41, 139.12, 143.70, 169.65; HRMS 7.09–7.17 (m, 2H); 13C NMR (100 MHz, CDCl3): d 18.38, 44.95,
(ESI) calcd for C16H16N2O [M + H]+ 253.1335, found [M + H]+ 52.43, 58.66, 128.46, 128.60, 129.02, 130.27, 135.32, 172.82;
253.1337.
HRMS (ESI) calcd for C11H14N2O [M + H]+ 191.1156, found
1-Phenyl-5-p-tolylimidazolidin-2-one (5d). Brownish viscous [M + H]+ 191.1155.
liquid; Rf (20% CH3COOEt/C6H14) 0.61; IR (n cmꢂ1, CHCl3):
1-Cyclohexyl-5-phenylimidazolidin-2-one (5k). Brownish
1706, 3380 cmꢂ1; 1H NMR (400 MHz, CDCl3): d 2.33 (s, 3H), 3.55 viscous liquid; Rf (20% CH3COOEt/C6H14) 0.67; IR (n cmꢂ1
,
(t, J ¼ 6.4 Hz, 2H), 4.44 (t, J ¼ 6.8 Hz, 1H), 4.96 (s, 1H, NH), 6.59– CHCl3): 1704, 3382 cmꢂ1; H NMR (400 MHz, CDCl3): d 0.83–
6.73 (m, 3H), 7.04–7.34 (m, 6H); 13C NMR (100 MHz, CDCl3): d 1.08 (m, 3H), 1.11–1.28 (m, 4H), 1.64 (t, J ¼ 1.4 Hz, 1H), 1.73 (d,
19.32, 44.16, 55.78, 113.46, 117.24, 126.77, 127.71, 128.23, J ¼ 3.5 Hz, 3H), 3.69 (t, J ¼ 6.4 Hz, 2H), 4.51 (t, J ¼ 6.7 Hz, 1H),
136.33, 139.21, 142.70, 170.16; HRMS (ESI) calcd for C16H16N2O 4.93 (s, 1H, NH), 6.96–7.00 (m, 1H), 7.17–7.32 (m, 4H); 13C NMR
1
[M + H]+ 253.1335, found [M + H]+ 253.1339.
(100 MHz, CDCl3): d 24.86, 25.66, 25.71, 28.44, 28.51, 52.76,
5-(2-Chlorophenyl)-1-phenylimidazolidin-2-one
(5e). 53.48, 62.97, 129.43, 129.86, 131.48, 132.19, 141.68, 171.62;
Brownish-yellow viscous liquid; Rf (20% CH3COOEt/C6H14) 0.65; HRMS (ESI) calcd for C15H20N2O [M + H]+ 245.1575, found
IR (n cmꢂ1, CHCl3): 1702, 3382 cmꢂ1 1H NMR (400 MHz, [M + H]+ 245.1574.
;
CDCl3): d 3.50 (t, J ¼ 6.5 Hz, 2H), 4.57 (t, J ¼ 6.4 Hz, 1H), 4.97 (s,
1H, NH), 6.64–6.76 (m, 3H), 7.05–7.37 (m, 6H); 13C NMR (100
MHz, CDCl3): d 45.19, 53.14, 112.67, 117.97, 126.62, 127.14,
127.78, 128.05, 128.57, 130.93, 139.51, 145.17, 170.86; HRMS
(ESI) calcd for C15H13ClN2O [M + H]+ 273.0789, found [M + H]+
273.0790.
Acknowledgements
The authors are thankful to the University Grant Commission
(UGC) New Delhi, for the nancial assistance and Sophisticated
Analytical Instrumentation Facility (SAIF) Punjab University,
Chandigarh for spectral analysis. R. Badru is thankful to UGC,
New Delhi for providing research fellowship (10-2(5)/2007(ii)-
E.U.II).
5-(3-Chlorophenyl)-1-phenylimidazolidin-2-one
(5f).
Brownish viscous liquid; Rf (20% CH3COOEt/C6H14) 0.68; IR (n
1
cmꢂ1, CHCl3): 1702, 3380 cmꢂ1; H NMR (400 MHz, CDCl3): d
3.51 (t, J ¼ 6.7 Hz, 2H), 4.59 (t, J ¼ 6.6 Hz, 1H), 4.99 (s, 1H, NH),
6.65–6.73 (m, 3H), 7.09–7.39 (m, 6H); 13C NMR (100 MHz,
CDCl3): d 44.01, 55.17, 117.62, 124.40, 126.68, 127.17, 127.67,
128.13, 129.10, 134.15, 139.12, 144.90, 171.27; HRMS (ESI) calcd
for C15H13ClN2O [M + H]+ 273.0789, found [M + H]+ 273.0789.
5-(4-Chlorophenyl)-1-phenylimidazolidin-2-one (5g). Brownish-
References
1 (a) D. Kaminskyy, B. Zimenkovsky and R. Lesyk, Eur. J. Med.
Chem., 2009, 44, 3627; (b) A. Mentrup, E. O. Renth,
K. Schromn and P. Danneberg, US Pat., 3 992 537, 1976; (c)
G. Prevost, S. Auvin, C. Lanco, A. M. Liberatore and
O. Lavergne, US Pat., 2012/0083514 A1, 2012; (d)
A. S. Guerra, D. J. Malta, L. P. Laranjeira, M. B. Maia,
N. C. Colaco, M. do C. de-Lima, S. L. Galdino, I. da R. Pitta
and T. Goncalves-Silva, Int. Immunopharmacol., 2011, 11,
1816; (e) D. Huber, J. D. Ehrhardt, N. Decker, J. Himber,
G. Andermann and G. Leclerc, J. Med. Chem., 1991, 34, 3197.
2 (a) A. Alexakis, P. Mangeney, N. Lensen, J. P. Tranchier,
R. Gosmini and S. Raussou, Pure Appl. Chem., 1996, 68,
531; (b) A. Alexakis and P. Mangeney, in Advanced
Asymmetric Synthesis, ed. G. R. Stephenson, Chapman and
Hall, London, 1996, p. 93; (c) A. Erkkila, I. Majander and
P. M. Pihko, Chem. Rev., 2007, 107, 5416; (d) C. Najera and
J. M. Sansano, Chem. Rev., 2007, 107, 4584.
yellow viscous liquid; Rf (20% CH3COOEt/C6H14) 0.67; IR (n cmꢂ1
,
CHCl3): 1704, 3384 cmꢂ1; 1H NMR (400 MHz, CDCl3): d 3.48 (t, J ¼
6.1 Hz, 2H), 4.57 (t, J ¼ 6.4 Hz, 1H), 4.97 (s, 1H, NH), 6.66–6.78 (m,
3H), 7.07–7.40 (m, 6H); 13C NMR (100 MHz, CDCl3): d 44.36, 57.31,
117.90, 126.14, 127.00, 127.90, 128.27, 129.13, 139.39, 141.70,
171.46; HRMS (ESI) calcd for C15H13ClN2O [M + H]+ 273.0789,
found [M + H]+ 273.0786.
5-(Furan-2-yl)-1-phenylimidazolidin-2-one (5h). Brownish
viscous liquid; Rf (20% CH3COOEt/C6H14) 0.63; IR (n cmꢂ1
,
CHCl3): 1702, 3384 cmꢂ1; 1H NMR (400 MHz, CDCl3): d 3.55 (t, J
¼ 6.5 Hz, 2H), 4.48 (t, J ¼ 6.8 Hz, 1H), 4.94 (s, 1H, NH), 6.36–6.45
(m, 4H), 6.96–7.24 (m, 4H); 13C NMR (100 MHz, CDCl3): d 49.95,
60.41, 117.80, 126.73, 127.56, 128.63, 128.91, 140.25, 142.98,
151.09, 171.15; HRMS (ESI) calcd for C13H12N2O2 [M + H]+
229.0972, found [M + H]+ 229.0974.
1-Phenyl-5-(thiphen-2-yl)imidazolidin-2-one (5i). Brownish
3 (a) T. Isobe, K. Fukuda and T. Ishikawa, J. Org. Chem., 2000,
65, 7770; (b) T. Isobe, K. Fukuda, T. Tokunaga, H. Seki,
K. Yamaguchi and T. Ishikawa, J. Org. Chem., 2000, 65,
7774; (c) T. Isobe, K. Fukuda, K. Yamaguchi, H. Seki,
T. Tokunaga and T. Ishikawa, J. Org. Chem., 2000, 65, 7779.
4 (a) W. Chen, R. Wu, Y. Li, L. S. Ding and Y. C. Chen,
Synthesis, 2006, 3058; (b) M. Dai, B. Liang, C. Wang,
J. Chen and Z. Yang, Org. Lett., 2004, 6, 221; (c) R. Li,
W. Chen, J. Shi, L. Chen, Y. Chen, L. Ding and Y. Wei, J.
Mass Spectrom., 2008, 43, 542.
viscous liquid; Rf (20% CH3COOEt/C6H14) 0.64; IR (n cmꢂ1
,
CHCl3): 1704, 3382 cmꢂ1; 1H NMR (400 MHz, CDCl3): d 3.69 (t, J
¼ 6.4 Hz, 2H), 4.47 (t, J ¼ 6.6 Hz, 1H), 5.02 (s, 1H, NH), 6.93–6.95
(m, 1H), 7.12–7.52 (m, 7H); 13C NMR (100 MHz, CDCl3): d 48.66,
61.85, 117.63, 127.71, 128.45, 129.06, 129.46, 129.91, 130.07,
139.13, 170.04; HRMS (ESI) calcd for C13H12N2OS [M + H]+
245.0743, found [M + H]+ 245.0740.
1-Ethyl-5-phenylimidazolidin-2-one (5j). Brownish viscous
liquid; Rf (20% CH3COOEt/C6H14) 0.66; IR (n cmꢂ1, CHCl3):
1704, 3380 cmꢂ1; 1H NMR (400 MHz, CDCl3): d 1.27 (t, J ¼ 8.52
Hz, 3H), 2.39–2.42 (q, J ¼ 7.8 Hz, 2H), 3.60 (t, J ¼ 6.6 Hz, 2H),
4.38 (t, J ¼ 7.6 Hz, 1H), 4.92 (s, 1H, NH), 6.81–6.97 (m, 3H),
5 B. M. York, US Pat., 4 540 700, 1985.
6 H. J. Patel, J. Sarra, F. Caruso, M. Rossi, U. Doshi and
R. A. Stephani, Bioorg. Med. Chem. Lett., 2006, 16, 4644.
38984 | RSC Adv., 2014, 4, 38978–38985
This journal is © The Royal Society of Chemistry 2014