Arkivoc 2017, v, 314-326
Ye, Q. et al.
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2-Methyl-4-n-octyl-1-tosyl-4,5-dihydro-1H-imidazole (3h). Viscous oil; H NMR (500 MHz, CDCl3) δ 7.75 (d, J
8.3 Hz, 2H, Ph), 7.36 (d, J 8.1 Hz, 2H, Ph), 3.86-3.81 (m, 2H, CH2N), 3.34 (dd, J 8.2, 6.3 Hz, 1H, CHN=), 2.46 (s, 3H,
Me in Ts), 2.29 (s, 3H, 2-Me), 1.29-1.23 (m, 14H, 7-CH2), 0.88 (t, J 7.0 Hz, 3H, CH3 in n-octyl). 13C NMR (125
MHz, CDCl3) δ 155.0, 144.6, 135.4, 130.0, 127.2, 63.6, 53.2, 35.8, 31.8, 29.5, 29.4, 29.2, 25.6, 22.6, 21.6, 16.8,
14.1; MS (ESI): ([M+H]+) 351.2. HRMS (ESI) calculated for C19H31N2O2S ([M+H]+) 351.2101, found 351.2028. El.
Anal. calculated for C19H30N2O2S: C, 65.11; H, 8.63; N, 7.99; found C, 65.32; H, 8.59; N, 8.21.
2-Methyl-1-tosyl-3a,4,5,6,7,7a-hexahydro-1H-benzimidazole (3i). White solid, mp 112-113 °C (lit. 115-117
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°C)31; H NMR (500 MHz, CDCl3) δ 7.71 (d, J 8.3 Hz, 2H, Ph), 7.36 (d, J 8.2 Hz, 2H, Ph), , 3.13-3.07 (m, 1H,
CHNTs), 2.88-2.82 (m, 1H, CH2), 2.57-2.54 (m, 1H, CH2), 2.46 (s, 3H, Me in Ts), 2.32, 2.31 (ss, 3H, 2-Me), 2.26-
2.23 (m, 1H, CH2), 1.88-1.78 (m, 2H, CH2), 1.68-1.60 (m, 1H, CHN=), 1.37-1.22 (m, 3H, CH2). 13C NMR (125 MHz,
CDCl3) δ 158.2, 144.6, 135.0, 130.0, 127.4, 70.2, 69.3, 30.56, 30.55, 25.0, 24.6, 21.6, 17.9. MS (ESI): ([M+H]+)
293.1.
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2,4-Diphenyl-1-tosyl-4,5-dihydro-1H-imidazole (3j). White solid, mp 164-165 °C (EtOAc-PE)29; H NMR (500
MHz, CDCl3) δ 7.80-7.78 (m, 2H, 2-Ph), 7.56-7.53 (m, 1H, Ph in Ts), 7.47-7.41 (m, 4H, Ph in Ts and 2-Ph), 7.25-
7.21 (m, 5H, Ph in Ts and 4-Ph), 6.70-6.98 (m, 2H, 4-Ph), 5.03-4.99 (m, 1H, CHN=), 4.48-4.43 (m, 1H, CH2), 3.90-
3.86 (m, 1H, CH2), 2.44 (s, 3H, Me). 13C NMR (125 MHz, CDCl3) δ 159.9, 144.7, 141.5, 134.5, 131.2, 130.1,
129.9, 129.8, 128.6, 127.7, 127.6, 127.4, 126.4, 67.8, 56.9, 21.6. MS (ESI): ([M+H]+) 377.1.
2-Benzyl-4-phenyl-1-tosyl-4,5-dihydro-1H-imidazole (3k). Colorless liquid29; 1H NMR (500 MHz, CDCl3) δ 7.43-
7.40 (m, 4H, Ph in Ts), 7.38-7.25 (m, 6H, 4-Ph and 2-Ph), 7.21-7.18 (m, 2H, 2-Ph), 7.04-7.7.03 (m, 2H, 2-Ph),
5.08-5.05 (m, 1H, CHN=), 4.20-4.14 (m, 3H, CH2 and CH2 in benzyl), 3.62-3.59 (m, 1H, CH2 in benzyl), 2.42 (s, 3H,
Me). 13C NMR (125 MHz, CDCl3) δ 158.3, 144.5, 141.7, 135.4, 134.9, 129.9, 129.4, 128.7, 128.5, 127.6, 127.3,
127.0, 126.4, 66.9, 55.5, 35.7, 21.5. MS (ESI): ([M+H]+) 391.1.
2-(1-Naphthalenyl)-4-phenyl-1-tosyl-4,5-dihydro-1H-imidazole (3l). White solid, mp 152-153 °C (EtOAc-PE);
1H NMR (500 MHz, CDCl3) δ 7.98 (d, J 8.2 Hz, 1H), 7.91 (d, J 8.4 Hz, 1H), 7.86 (d, J 8.1 Hz, 1H), 7.73 (d, J 6.8 Hz,
1H), 7.56-7.52 (m, 1H), 7.51-7.47 (m, 1H), 7.43-7.40 (m, 1H), 7.37-7.23 (m, 7H), 7.02 (d, J 8.1 Hz, 2H, Ph), 5.36
(dd, J 9.9, 8.8 Hz, 1H, CH2), 4.62-4.58 (m, 1H, CH2), 4.05 (dd, J 10.5, 8.4 Hz,1H, CHN=), 2.34 (s, 3H, Me in Ts). 13C
NMR (125 MHz, CDCl3) δ 157.7, 144.5, 141.6, 134.6, 133.2, 131.4, 130.8, 129.4, 128.8, 128.3, 127.7, 127.6,
127.3, 126.7, 126.5, 125.9, 125.2, 124.4, 68.2, 55.8, 21.5. MS (ESI): ([M+H]+) 427.2; HRMS (ESI) calculated for
C26 H23N2O2S ([M+H]+) 427.1494, found 427.1475. El. Anal. calculated for C26H22N2O2S: C, 73.21; H, 5.20; N,
6.57; found C, 73.11; H, 5.36; N, 6.79.
2-(p-Benzonitrile)-4-phenyl-1-tosyl-4,5-dihydro-1H-imidazole (3m). White solid, mp 151-153 °C (EtOAc-PE);
1H NMR (500 MHz, CDCl3) δ 7.92 (d, J 8.3 Hz, 2H, 2-Ph), 7.75 (d, J 8.3 Hz,, 2H, Ph in Ts), 7.42 (d, J 8.2 Hz, 2H, Ph
in Ts), 7.27-7.23 (m, 5H, 4-Ph), 6.97-6.95 (m, 2H, 2-Ph), 5.07-5.03 (m, 1H, CH2), 4.47-4.43 (m, 1H, CH2), 3.88
(dd, J 11.4, 8.1 Hz, 1H, CHN=), 2.46 (s, 3H, Me). 13C NMR (125 MHz, CDCl3) δ 158.4 145.2, 140.9, 134.7, 134.1,
132.8, 131.6, 130.5, 130.0, 128.7, 127.7, 127.6, 126.3, 118.2, 114.7, 68.4, 56.8, 21.6. MS (ESI): ([M+H]+) 402.1;
HRMS (ESI) calculated for C23H20N3O2S ([M+H]+) 402.1259, found 402.1271. El. Anal. calculated for C23H19N3O2S:
C, 68.81; H, 4.77; N, 10.47; found C, 68.92; H, 4.78; N, 10.32.
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4-Phenyl-2-(p-tolyl)-1-tosyl-4,5-dihydro-1H-imidazole (3n). Colorless liquid; H NMR (500 MHz, CDCl3) δ 7.71
(d, J 8.1 Hz, 2H, Ph in Ts), 7.43 (d, J 8.3 Hz, 2H, Ph in Ts), 7.28-7.26 (m, 2H, 2-Ph), 7.24-7.20 (m, 5H, 4-Ph), 6.98-
6.96 (m, 2H, 2-Ph), 4.96 (dd, J 9.5, 8.4 Hz, 1H, CHN=), 4.43 (dd, J 11.4, 10.0 Hz, 1H, CH2), 3.85 (dd, J 11.5, 8.1 Hz,
1H, CH2), 2.45(s, 3H, Me in Ts), 2.44 (s, 3H, Me in tolyl). 13C NMR (125 MHz, CDCl3) δ 160.0, 144.6, 141.7, 141.6,
134.5, 129.9, 129.8, 128.9, 128.54, 128.45, 127.6, 127.4, 127.3, 127.2, 127.0, 126.3, 67.8, 56.9, 21.63, 21.59.
MS (ESI): ([M+H]+) 391.2; HRMS (ESI) calculated for C23H23N2O2S ([M+H]+) 391.1492, found 391.1475. El. Anal.
calculated for C23H22N2O2S: C, 70.74; H, 5.68; N, 7.17; found C, 70.58; H, 5.77; N, 7.33.
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