Investigation of the Mitsunobu Reaction of N-(2-Hydroxyethyl)-N′-Phenyl-Ureas

References

• Mitsunobo , O. 1981 . Synthesis , : 1 – 28 . For general reviews, see:
   Google Scholar
• Hughes , D. L. 1992 . Org. React. , 42 : 335 – 656 .
   Web of Science ®Google Scholar
• Comins , D. L. and Gao , J. 1994 . Tetrahedron Lett. , 35 : 2819 – 2822 .
   Web of Science ®Google Scholar
• Walker , M. A. J. 1995 . Org. Chem. , 60 : 5352 – 5355 .
   Web of Science ®Google Scholar
• Edwards , M. L. , Stemerick , D. M. and McCarthy , J. R. 1990 . Tetrahedron Lett. , 31 : 3417 – 3420 .
   Google Scholar
• Fukuyama , T. , Jow , C. K. and Cheung , M. 1995 . Tetrahedron Lett. , 36 : 6373 – 6374 .
   Web of Science ®Google Scholar
• Fabiano , E. , Golding , B. T. and Sadeghi , M. M. 1987 . Synthesis , : 190
   Web of Science ®Google Scholar
• Roush , D. M. and Patel , M. M. 1985 . Syn. Comm. , 15 : 675 – 679 .
   Web of Science ®Google Scholar
• Galeotti , N. , Montagne , C. , Poncet , J. and Jouin , P. 1992 . Tetrahedron Lett. , 33 : 2807 – 2810 .
   Web of Science ®Google Scholar
• Wipf , P. and Miller , C. P. 1992 . Tetrahedron Lett. , 33 : 6267 – 6270 .
   Web of Science ®Google Scholar
• Koppel , I. , Koppel , J. , Koppel , I. , Leito , I. , Pihl , I. , Wallin , V. , Grehn , A. L. and Ragnarsson , U. J. 1993 . Chem. Soc. Perkin Trans. , 2 : 655 – 658 .
   Google Scholar
• 1-Phenyl-2-imidazolidinone (2b). mp 162–163 °C (lit.10 mp 161–163 °C); 1H NMR (300 MHz, CDCl3)11 7.56–7.52 (m, 2H), 7.37–7.26 (m, 2H), 7.08–7.06 (m, 1H), 3.97–3.92 (m, 2H), 3.62–3.55 (m, 2H); 13C NMR (CDCl3) 159.90, 140.01, 128.82, 122.27, 117.88, 45.32, 37.49; IR (CDCl3) 1684 (s) cm-1; HRMS calcd for C9H11N2O 162.0793, found 162.0726., 1-Methyl-3-phenyl-2-imidazolidinone (2d). mp 108–110 °C (lit.12 mp 110–111 °C); 1H NMR (300 MHz, CDCl3) 7.57–7.53 (m, 2H), 7.35–7.26 (m, 2H), 7.04–6.99 (m. 1H), 3.81–3.76 (m, 2H), 3.47–3.42 (m, 2H), 2.89 (s, 3H); 13C NMR (CDCl3) 158.16, 140.62, 128.70, 122.16, 117.20, 44.05, 42.25, 31.16; IR(CDCl3) 1696 (s) cm-1., 1-Ethyl-3-phenyl-2-imidazolidinone (2e). mp 81–82 °C (lit.12 mp 83 °C); 1H NMR (300 MHz, CDCl3) 7.57–7.54 (m, 2H), 7.35–7.26 (m, 2H), 7.04–6.99 (m, 1H), 3.82–3.78 (m, 2H), 3.49–3.44 (m, 2H), 3.31 (q, 2H, J = 7.2 Hz), 1.17 (t, 3H. J = 7.2 Hz); 13C NMR (CDCl3) 157.58, 140.18, 128.63, 122.03, 117.14, 42.30, 41.01, 38.50, 12.51; IR (CDCl3) 1701 (s) cm-1; HRMS calcd for C11H14N2O 190.1106, found 190.1098., (4S)-4-(1-Methylethyl)-1-phenyl-2-imidazolidinone (2i). mp 80–86 °C; 1H NMR (300 MHz, CDCl3) 7.56–7.53 (m, 2H), 7.35–7.12 (m, 2H), 7.05–7.02(m, 1H), 6.32 (bs. 1H), 3.95–3.88 (m, 1H), 3.57–3.47 (m, 2H), 1.79–1.69 (m, 1H), 0.98 (d. 3H, J = 6.7 Hz). 0.92 (d, 3H, J = 6.7 Hz); 13C NMR (CDCl3) 159.28. 140.15, 128.71, 122.34, 117.58, 54.79, 48.95, 33.12, 17.98, 17.00; IR (CDCl3) 1716 (s) cm-1., (4S)-1-Phenyl-4-phenylmethyl-2-imidazolidinone (2j). mp 115–117 °C; 1H NMR (300 MHz, CDCl3) 7.53–7.20 (m. 10H), 4.95 (bs, 1H), 4.04–3.95 (m, 2H). 3.65–3.61 (m. 1H), 2.92–2.84 (m, 2H); 13C NMR (CDCl3) 158.67, 139.91. 136.62. 129.34, 129.05, 128.85, 128.78, 128.51, 127.01. 122.71, 117.81,50.41, 50.39, 42.19; IR (CDCl3) 1705 (s) cm-1; HRMS calcd for C16H16N2O 252.1263, found 252.1266., 4,5-Dihydro-N-phenyl-2-oxazolamine(3b). mp: 110–112 °C(lit.13 mp 119–120 °C)1H NMR (300 MHz, CDCl3)11 7.31–7.22 (m, 4H), 7.03–6.97 (m, 1H), 4.37 (t, 2H, J = 8.4 Hz), 3.86 (t, 2H, J = 8.4 Hz)., 4,5-Dihydro-4-methyl-N-phenyl-2-oxazolamine(3f). 1H NMR (300 MHz, CDCl3) 7.27–7.25(m, 4H), 6.99–6.98(m, 1H), 4.43(t, 1H), 4.19–4.12(m, 1H), 3.87(t, 1H), 1.28(d, 3H, J=6.4 Hz)., 4,4-Dimethyl-4,5-dihydro-N-phenyl-2-oxaolamine(3h). mp: 127–8 °C; 1H NMR (300 MHz, CDCl3) 7.36–7.25 (m, 4H), 7.05–6.95 (m, 1H), 4.03 (s, 2H), 1.32 (s, 6H); 'C NMR (CDCl3) 155.42, 128.83, 122.19, 120.11, 78.56, 28.10; IR (CDCl3) 1688 (s) cm-1; HRMS calcd for C11H14N2O 190.1106, found 190.1109., 4,5-Dihydro-(4S)-4-(1-methylethyl)-N-phenyl-2-oxazolamine(3i). mp: 123–126 °C; 1H NMR (300 MHz, CDCI3) 7.29–7.24(m, 4H), 7.01–6.95(m, 1H), 4.37(t, 1H), 4.08(t, 1H), 3.77(m, 1H), 1.75(m, 1H), 0.97(d, 3H, J=6.6 Hz), 0.94(d, 3H. J=6.9 Hz); 13C NMR (CDCl3) 156.33, 128.83, 122.19, 120.11,70.15,54.86,32.98, 18.62, 17.98; IR (CDCl3)1686 (s) cm-1.
   Google Scholar
• Heine , H. W. , Kenyon , W. G. and Johnson , E. M. 1961 . J. Am. Chem. Soc. , 83 : 2570 – 2574 .
   Google Scholar
• Araki , T. , Nogami , F. , Tsukube , H. , Nagata , K. and lyoshi , S. 1978 . J. Polym. Sci. Polym. Chem. Ed. , 16 : 1037 – 1057 .
   Web of Science ®Google Scholar
• Helmut , T. Ger. Patent . 1,126.392. . 1962 .
   Google Scholar
• 1962 . Chem. Abstr. , 57 : 9859i
   Google Scholar
• Mukaiyama , T. , Fujisawa , T. , Nohira , H. and Hyugaji , T. 1962 . J. Org Chem. , 27 : 3337 – 3340 .
   Google Scholar