Helvetica Chimica Acta – Vol. 90 (2007)
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Mþ ), 202 (100), 158 (46), 103 (56), 77 (27). Anal. calc. for C12H14N2O2 (218.26): C 66.04, H 6.47, N12.84;
found: C 66.15, H 6.35, N12.42.
4,5-Diphenyl-1H-imidazole-1-ethanol 3-Oxide (11c). Yield3) 251 mg (89%). Colorless solid. M.p.
197 – 1988 (CHCl3/petroleum ether). IR: 3350 – 2600vs (br.), 1443m, 1393m, 1350s, 1200m, 1076m, 844m,
772s, 753vs, 694s, 658m. 1H-NMR (CDCl3): 8.46 (s, HÀC(2)); 7.49 – 7.23 (m, 10 arom. H); 4.01, 3.71 (2t, 2
CH2). 13C-NMR (CDCl3): 130.7, 129.7, 129.5, 129.0, 128.5, 128.0 (6d, 10 arom. CH); 129.8, 127.7, 126.4,
.
125.7 (4s, 2 arom. C, C(4), C(5)); 127.6 (d, C(2)); 59.9, 48.6 (2t, 2 CH2). EI-MS: 280 (31, Mþ ), 264 (100),
219 (48), 165 (68), 103 (71), 77 (57). Anal. calc. for C17H16N2O2 · 0.1 H2O (282.13): C 72.37, H 5.79, N
9.93; found: C 72.34, H 5.71, N9.64.
4-Methyl-5-phenyl-1H-imidazole-1-ethanol 3-Oxide (11d). Yield3) 120 mg (55%). Colorless solid.
M.p. 165 – 1678 (acetone). IR: 3250 – 2550vs (br.), 1501m, 1444m, 1395s, 1380m, 1337vs, 1165s, 1080s,
871m, 757s, 703s, 646m. 1H-NMR (CDCl3): 8.36 (s, HÀC(2)); 7.56 – 7.42 (m, 5 arom. H); 4.02, 3.62 (2t, 2
CH2); 2.15 (s, Me). 13C-NMR (CDCl3): 130.8, 129.6, 129.3 (3d, 5 arom. CH); 127.8, 127.4, 126.8 (3s, arom.
.
C, C(4), C(5)); 60.5, 49.1 (2t, 2 CH2); 7.6 (q, Me). EI-MS: 218 (76, Mþ ), 202 (100), 130 (63), 104 (72).
Anal. calc. for C12H14N2O2 (218.26): C 66.04, H 6.47, N12.84; found: C 66.38, H 6.43, N12.46.
5-Methyl-4-phenyl-1H-imidazole-1-propanol 3-Oxide (11e). Yield after CC (Rf 0.59; SiO2, AcOEt/
MeOH 6 :4): 218 mg (94%). Colorless solid. M.p. 140 – 1428 (acetone). IR: 3350 – 2550vs (br.), 1497m,
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1467m, 1400m, 1363s, 1344s, 1315m, 1253s, 1231m, 1064s, 930m, 766s, 712s, 702s, 695s, 608s. H-NMR
(CD3OD): 8.31 (s, HÀC(2)); 7.59 – 7.40 (m, 5 arom. H); 4.14, 3.59 (2t, 2 CH2); 2.29 (s, Me); 1.99 (m, CH2).
13C-NMR (CD3OD): 131.1, 129.8, 129.5 (3d, 5 arom. CH); 130.6, 128.2, 125.2 (3s, arom. C, C(4), C(5));
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127.8 (d, C(2)); 58.9, 44.0, 33.7 (3t, 3 CH2); 9.2 (q, Me). EI-MS: 232 (5, Mþ ), 214 (100), 117 (47), 55 (49).
Anal. calc. for C13H16N2O2 (232.28): C 67.22, H 6.94, N12.06; found: C 67.46, H 7.06, N11.70.
4,5-Diphenyl-1H-imidazole-1-propanol 3-Oxide (11f). Yield3) 140 mg (47%). Colorless solid.
M.p. 191 – 1938 (acetone). IR: 3350 – 2650vs (br.), 1445m, 1392s, 1345s, 1198m, 1078s, 769s, 756s, 698s,
657m. 1H-NMR (CD3OD): 8.51 (s, HÀC(2)); 7.48 – 7.26 (m, 10 arom. H); 4.09, 3.48 (2t, 2 CH2); 1.81 (m,
CH2). 13C-NMR (CD3OD): 132.1, 131.2, 130.9, 130.3, 129.7, 129.2, 128.9 (7d, 10 arom. CH, C(2)); 131.4,
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129.3, 128.5, 127.8 (4s, 2 arom. C, C(4), C(5’)); 59.0, 44.8, 33.8 (3t, 3 CH2). EI-MS: 294 (7, Mþ ), 276 (75),
165 (19), 117 (100), 104 (19), 77 (22). Anal. calc. for C18H18N2O2 · 0.25 H2O (298.86): C 72.34, H 6.24, N
9.37; found: C 72.26, H 6.08, N9.30.
4-Methyl-5-phenyl-1H-imidazole-1-propanol 3-Oxide (11g). Yield after CC (Rf 0.65, SiO2, AcOEt/
MeOH 1:1): 153 mg (66%). Colorless solid. M.p. 139 – 1408 (CH2Cl2/petroleum ether). IR: 3250 – 2650vs
(br.), 1463m, 1389m, 1379m, 1325s, 1165s, 1091m, 1076m, 942w, 773s, 705m, 643m. 1H-NMR (CD3OD):
8.37 (s, HÀC(2)); 7.56 – 7.40 (m, 5 arom. H); 4.07, 3.43 (2t, 2 CH2); 1.76 (m, CH2). 13C-NMR (CD3OD):
131.5, 130.8, 130.3 (3d, 5 arom. CH); 128.5, 128.4, 127.4 (3s, arom. C, C(4), C(5)); 128.0 (d, C(2)); 58.9,
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44.6, 33.8 (3t, 3 CH2); 7.6 (q, Me). EI-MS: 232 (22, Mþ ), 214 (100), 171 (52), 117 (76), 104 (29), 55 (29).
Anal. calc. for C13H16N2O2 (232.28): C 67.22, H 6.94, N12.06; found: C 67.37, H 7.05, N12.01.
a,5-Dimethyl-4-phenyl-1H-imidazole-1-ethanol 3-Oxide (11h). Yield3) 211 mg (90%). Colorless
solid. M.p. 143 – 1458 (acetone). IR: 3400 – 2600vs (br.), 1610m, 1497m, 1444m, 1377s, 1349s, 1260m,
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1218m, 1136m, 1079m, 1029m, 767s, 720m, 700s, 678m, 608m. H-NMR (CD3OD): 8.25 (s, HÀC(2));
7.58 – 7.37 (m, 5 arom. H); 4.07 – 4.01 (m, CH2); 3.87 – 3.82 (m, CH(OH)); 2.28 (s, Me); 1.22 (d, J ¼ 4.6,
Me). 13C-NMR (CD3OD): 131.2, 129.7, 129.5 (3d, 5 arom. CH); 130.4, 128.3, 125.7 (3s, arom. C, C(4),
.
C(5)); 128.4 (d, C(2)); 67.3 (d, CH); 53.8 (t, CH2); 20.7, 9.5 (2q, 2 Me). EI-MS: 232 (62, Mþ ), 216 (100),
174 (64), 159 (72), 130 (40), 103 (58). Anal. calc. for C13H16N2O2 · 0.125 H2O (234.53): C 66.58, H 6.98, N
11.94; found: C 66.89, H 6.98, N11.82.
a-Methyl-4,5-diphenyl-1H-imidazole-1-ethanol 3-Oxide (11i). Yield3) 274 mg (92%). Colorless
solid. M.p. 182 – 1848 (CH2Cl2/petroleum ether). IR: 3350 – 2550vs (br.), 1486m, 1445m, 1398m, 1353s,
1265m, 1187m, 1138m, 763s, 701s, 656m. 1H-NMR (CD3OD): 8.48 (s, HÀC(2)); 7.45 – 7.28 (m, 10 arom.
H); 3.99 – 3.77 (m, CH2, CH); 1.04 (d, J ¼ 4.2, Me). 13C-NMR (CD3OD): 132.3, 131.2, 130.9, 130.2, 129.7,
129.1 (6d, 10 arom. CH); 131.0, 129.2, 128.4, 127.8 (4s, 2 arom. C, C(4), C(5)); 129.3 (d, C(2)); 66.8 (d,
.
CH); 54.2 (t, CH2); 20.7 (q, Me). EI-MS: 294 (2, Mþ ), 278 (11), 105 (100), 77 (35), 43 (46). Anal. calc.
for C18H18N2O2 · 0.25 H2O (298.86): C 72.34, H 6.24, N9.37; found: C 72.29, H 6.24, N8.98.
(aS)-a,4,5-Trimethyl-1H-imidazole-1-ethanol 3-Oxide (11j). Yield after CC (Rf 0.59; SiO2, AcOEt/
MeOH 6 :4): 141 mg (82%). Colorless solid. M.p. 119 – 1208 (acetone). [a]1D7 þ 42 (c ¼ 1, MeOH). IR: