N. Kise et al. / Tetrahedron 74 (2018) 992e1001
999
IR (ATR) 1632 cmꢁ1; 1H NMR (CDCl3)
(s, 3H), 5.40 (s, 1H), 7.06e7.10 (m, 4H), 7.25e7.34 (m, 6H); 13C NMR
(CDCl3) 8.4 (q), 28.5 (q), 29.0 (q), 46.9 (d), 118.1 (s), 120.7 (s), 127.2
(d), 128.7 (d), 128.9 (d), 139.7 (s), 152.4 (s). Anal. Calcd for
19H20N2O: C, 78.05; H, 6.90; N, 9.58. Found: C, 78.08; H, 6.91; N,
d
1.44 (s, 3H), 3.12 (s, 3H), 3.35
(M þ Hþ) 305.1654; found 305.1650.
d
4.4.17. 1-(Bis(4-fluorophenyl)methyl)-2-methyl-2,5,6,7-tetrahydro-
3H-pyrrolo[1,2-c]imidazol-3-one (4o)
C
Yellow paste; Rf 0.2 (ethyl acetate-ethyl alcohol, 10:1); IR (ATR)
9.47.
1647, 1618, 1601, 1504 cmꢁ1
;
1H NMR (CDCl3)
d
1.68 (t, 2H,
J ¼ 7.4 Hz), 2.13e2.20 (m, 2H), 3.00 (s, 3H), 3.84e3.90 (m, 2H), 5.15
(s, 1H), 7.00e7.09 (m, 8H); 13C NMR (CDCl3)
22.1 (t), 27.2 (t), 28.3
4.4.11. 4-(Bis(4-fluorophenyl)methyl)-1,3,5-trimethyl-1,3-dihydro-
2H-imidazol-2-one (4i)
d
(q), 42.8 (t), 45.7 (d), 115.3 (d, JCCF ¼ 20.7 Hz), 116.2 (s), 125.6 (s),
130.1 (d, JCCCF ¼ 8.4 Hz), 135.6 (s, JCCCCF ¼ 3.6 Hz), 149.5 (s), 161.6 (s,
JCF ¼ 246.8 Hz); HRMS (ESI) calcd for C20H19F2N2O (M þ Hþ)
341.1465; found 341.1460.
Yellow paste; Rf 0.25 (ethyl acetate-ethyl alcohol, 20:1); IR (ATR)
1707, 1670, 1643, 1601, 1504 cmꢁ1
;
1H NMR (CDCl3)
d
1.45 (s, 3H),
2.97 (s, 3H), 3.18 (s, 3H), 5.34 (s, 1H), 6.99e7.07 (m, 8H); 13C NMR
(CDCl3)
d
8.4 (q), 27.0 (q), 27.6 (q), 45.5 (q), 115.4 (d, JCCF ¼ 21.6 Hz),
116.1 (s), 118.2 (s), 130.2 (d, JCCCF ¼ 7.2 Hz), 136.1 (s, JCCCCF ¼ 3.6 Hz),
153.1 (s), 161.6 (s, JCF ¼ 245.9 Hz); HRMS (ESI) calcd for C19H19F2N2O
(M þ Hþ) 329.1465; found 329.1460.
4.4.18. 1-(Bis(4-methoxyphenyl)methyl)-2-methyl-2,5,6,7-
tetrahydro-3H-pyrrolo[1,2-c]imidazol-3-one (4p)
Yellow paste; Rf 0.25 (ethyl acetate-ethyl alcohol, 10:1); IR (ATR)
1672, 1647, 1609 cmꢁ1
;
1H NMR (CDCl3)
d
1.68 (t, 2H, J ¼ 7.6 Hz),
4.4.12. 4-(Bis(4-methoxyphenyl)methyl)-1,3,5-trimethyl-1,3-
dihydro-2H-imidazol-2-one (4j)
2.09e2.16 (m, 2H), 2.96 (s, 3H), 3.72 (t, 2H, J ¼ 6.9 Hz), 3.80 (s, 6H),
5.06 (s, 1H), 6.82e6.86 (m, 4H), 6.99e7.03 (m, 4H); 13C NMR (CDCl3)
Red paste; Rf 0.45 (ethyl acetate-ethyl alcohol, 10:1); IR (ATR)
d 22.1 (t), 27.4 (t), 27.9 (q), 42.1 (t), 45.8 (d), 54.9 (q), 113.6 (d), 116.4
1670, 1645, 1609, 1508 cmꢁ1; 1H NMR (CDCl3)
d
1.46 (s, 3H), 3.02 (s,
3H), 3.22 (s, 3H), 3.81 (s, 6H), 5.28 (s, 1H), 6.83e6.87 (m, 4H),
6.98e7.02 (m, 4H); 13C NMR (CDCl3)
8.3 (q), 27.3 (q), 27.9 (q), 45.2
(s), 124.6 (s), 129.5 (d), 132.6 (s), 149.9 (s), 158.2 (s); HRMS (ESI)
calcd for C22H25N2O3 (M þ Hþ) 365.1865; found 365.1861.
d
(d), 54.9 (q), 113.6 (s), 116.3 (s), 119.6 (s), 129.6 (d), 132.4 (s), 152.7
(s), 158.2 (s); HRMS (ESI) calcd for C21H25N2O3 (M þ Hþ) 353.1865;
found 353.1862.
4.4.19. 4-(Hydroxydiphenylmethyl)-1,3-dimethyl-1,3-dihydro-2H-
imidazol-2-one (5a)
White solid; Rf 0.2 (ethyl acetate); mp 216e218 ꢀC; IR (ATR)
3218, 3152, 1672, 1649 cmꢁ1; 1H NMR (CDCl3)
d
2.97 (s, 3H), 3.08 (s,
3H), 4.95 (s, 1H), 5.35 (s, 1H), 7.25e7.34 (m, 6H), 7.36e7.39 (m, 4H);
13C NMR (CDCl3)
29.7 (q), 30.4 (q), 76.6 (s), 112.2 (d), 126.9 (d),
127.5 (d), 127.7 (s), 128.0 (d), 143.9 (s), 154.2 (s). Anal. Calcd for
18H18N2O2: C, 73.45; H, 6.16; N, 9.52. Found: C, 73.48; H, 6.16; N,
4.4.13. 4-Benzhydryl-5-isobutyl-1,3-dimethyl-1,3-dihydro-2H-
imidazol-2-one (4k)
d
Yellow paste; Rf 0.2 (ethyl acetate); IR (ATR) 1616 cmꢁ1; 1H NMR
(CDCl3)
J ¼ 7.6 Hz), 3.02 (s, 3H), 3.39 (s, 3H), 5.51 (s, 1H), 7.06e7.12 (m, 4H),
7.24e7.34 (m, 6H); 13C NMR (CDCl3)
21.8 (q), 28.9 (d), 29.1 (q), 29.6
d
0.72 (d, 6H, J ¼ 6.6 Hz), 1.49e1.58 (m, 1H), 1.85 (d, 2H,
C
9.48.
d
(q), 31.1 (t), 46.3 (d),120.9 (s),122.0 (s),127.0 (d),128.5 (d),128.8 (d),
139.4 (s), 152.4 (s); HRMS (ESI) calcd for C22H27N2O (M þ Hþ)
335.2123; found 335.2118.
4.4.20. 4-(Bis(4-fluorophenyl)(hydroxy)methyl)-1,3-dimethyl-1,3-
dihydro-2H-imidazol-2-one (5b)
White solid; Rf 0.55 (ethyl acetate-ethanol, 10:1); mp
249e250 ꢀC; IR (ATR) 3190, 1661, 1601 cmꢁ1; 1H NMR (CDCl3)
d
2.96
(s, 3H), 3.09 (s, 3H), 5.21 (s, 1H), 5.35 (s, 1H), 6.98e7.05 (m, 4H),
7.30e7.37 (m, 4H); 13C NMR (CDCl3)
29.2 (q), 29.9 (q), 75.3 (s),
4.4.14. 4-Benzhydryl-5-benzyl-1,3-dimethyl-1,3-dihydro-2H-
imidazol-2-one (4l)
d
Yellow paste; Rf 0.25 (hexanes-ethyl acetate, 1:5); IR (ATR) 1711,
111.6 (d), 114.3 (d, JCCF ¼ 21.6 Hz), 126.9 (s), 128.4 (d, JCCCF ¼ 8.4 Hz),
139.7 (s, JCCCCF ¼ 2.4 Hz), 153.8 (s), 161.5 (s, JCF ¼ 246.2 Hz). Anal.
Calcd for C18H16F2N2O2: C, 65.45; H, 4.88; N, 8.48. Found: C, 65.40;
H, 4.93; N, 8.43.
1618 cmꢁ1; 1H NMR (CDCl3)
d
3.08 (s, 3H), 3.12 (s, 3H), 3.31 (s, 2H),
5.50 (s, 1H), 6.87e6.91 (m, 2H), 7.06e7.11 (m, 4H), 7.12e7.28 (m,
9H); 13C NMR (CDCl3)
28.3 (t), 28.6 (q), 29.3 (q), 46.8 (d), 119.9 (s),
d
122.1 (s), 126.4 (d), 127.1 (d), 127.4 (d), 128.4 (d), 128.6 (d), 128.8 (d),
136.9 (s), 139.4 (s), 152.8 (s); HRMS (ESI) calcd for C25H25N2O
(M þ Hþ) 369.1967; found 369.1961.
4.4.21. 4-(9-Hydroxy-9,10-dihydroanthracen-9-yl)-1,3-dimethyl-
1,3-dihydro-2H-imidazol-2-one (5d)
White solid; Rf 0.4 (ethyl acetate-ethanol, 20:1); mp
4.4.15. 4-Benzhydryl-5-isopropyl-1,3-dimethyl-1,3-dihydro-2H-
imidazol-2-one (4m)
235e236 ꢀC; IR (ATR) 3231, 1663 cmꢁ1 1H NMR (CDCl3)
; d 2.86 (s,
3H), 3.09 (s, 3H), 3.86 (s, 1H), 3.95 (d, 1H, J ¼ 18.4 Hz), 4.02 (d, 1H,
Yellow paste; Rf 0.25 (hexanes-ethyl acetate, 1:5); IR (ATR) 1647,
J ¼ 8.4 Hz), 5.69 (s, 1H), 7.27e7.34 (m, 6H), 7.68e7.72 (m, 2H); 13C
1624 cmꢁ1; 1H NMR (CDCl3)
d
1.09 (d, 6H, J ¼ 7.3 Hz), 2.61e2.69 (m,
1H), 3.02 (s, 3H), 3.49 (s, 3H), 5.61 (s, 1H), 7.07e7.12 (m, 4H),
7.24e7.34 (m, 6H); 13C NMR (CDCl3)
20.7 (q), 23.9 (d), 29.9 (q),
NMR (CDCl3) d 28.8 (q), 29.9 (q), 35.0 (t), 71.5 (s), 109.8 (d), 124.5 (s),
125.8 (d), 126.0 (d), 127.1 (d), 127.3 (d), 135.6 (s), 139.5 (s), 153.5 (s).
Anal. Calcd for C19H18N2O2: C, 74.49; H, 5.92; N, 9.14. Found: C,
74.47; H, 5.92; N, 9.09.
d
30.4 (q), 46.1 (d), 120.2 (s), 126.9 (s), 127.1 (d), 128.7 (d), 128.8 (d),
139.6 (s), 152.6 (s); HRMS (ESI) calcd for C21H25N2O (M þ Hþ)
321.1967; found 321.1963.
4.4.22. 4-(5-Hydroxy-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-
yl)-1,3-dimethyl-1,3-dihydro-2H-imidazol-2-one (5e)
4.4.16. Benzhydryl-2-methyl-2,5,6,7-tetrahydro-3H-pyrrolo[1,2-c]
imidazol-3-one (4n)
White solid; Rf 0.15 (ethyl acetate); mp 261e262 ꢀC; IR (ATR)
3159, 1670 cmꢁ1; 1H NMR (CDCl3)
d 2.73 (s, 3H), 2.76e2.85 (m, 2H),
Yellow paste; Rf 0.25 (ethyl acetate-ethanol, 10:1); IR (ATR)
3.08 (s, 3H), 3.15e3.24 (m, 2H), 4.52 (brs,1H), 5.44 (s,1H), 7.05e7.09
1684, 1653 cmꢁ1
;
1H NMR (CDCl3)
d
1.63 (t, 2H, J ¼ 7.5 Hz),
2.07e2.14 (m, 2H), 2.93 (s, 3H), 3.62 (t, 2H, J ¼ 7.2 Hz), 5.16 (s, 1H),
7.09e7.15 (m, 4H), 7.23e7.35 (m, 6H); 13C NMR (CDCl3)
22.1 (t),
(m, 2H), 7.17e7.25 (m, 4H), 7.97e8.01 (m, 2H); 13C NMR (CDCl3)
d
28.8 (q), 30.5 (q), 32.1 (t), 72.3 (s), 111.0 (d), 125.6 (d), 126.0 (d),
d
127.7 (d), 127.8 (s), 130.2 (d), 137.1 (s), 141.6 (s), 153.5 (s). Anal. Calcd
for C20H20N2O2: C, 74.98; H, 6.29; N, 8.74. Found: C, 74.95; H, 6.30;
N, 8.68.
27.4 (t), 27.7 (q), 41.6 (t), 47.6 (d), 115.3 (s), 124.4 (s), 126.8 (d), 128.3
(d), 128.7 (d), 140.5 (s), 150.3 (s); HRMS (ESI) calcd for C20H21N2O