Gorakh S. Yellol et al.
FULL PAPERS
Methyl (2S)-2-(3-butyl-4-phenyl-2-thioxo-2,3-dihydro-1H-
imidazol-1-yl)-3-phenylpropanoate (7c): H NMR (300 MHz,
(300 MHz, CDCl3): d=7.44–7.38 (m, 3H), 7.33–7.31 (m,
2H), 5.70 (s, 1H), 3.94–3.76 (m, 1H), 3.70 (s, 3H), 3.69–3.59
(m, 2H), 1.85–1.69 (m, 3H), 1.54–1.36 (m, 2H), 1.13–1.01
(m, 2H); 0.96–0.86 (m, 6H); 0.70 (t, J=7.2 Hz, 3H);
13C NMR (75 MHz, CDCl3): d=174.4, 161.2, 140.8, 132.2,
128.9, 128.8, 128.6, 95.0, 65.7, 51.8, 44.7, 43.1, 29.9, 24.9, 23.3,
21.9, 19.6, 13.7; MS (EI): m/z=360; HR-MS (EI): m/z=
360.1871, calcd. for C20H28N2O2S: 360.1871; [a]2D5: À31.4 (c
1.0, CH2Cl2); IR (KBr): n=2954, 1745, 1613, 1444 cmÀ1.
Methyl (2S)-2-[3-benzyl-4-(naphthalen-2-yl)-2-thioxo-2,3-
1
CDCl3): d=7.42–7.40 (m, 3H), 7.34–7.29 (m, 5H), 7.24–7.17
(m, 2H), 5.69 (s, 1H), 3.92–3.81 (m, 2H), 3.71 (s, 3H), 3.65–
3.58 (m, 1H), 3.29 (dd, J=13.4, 5.4 Hz, 1H), 3.15–3.12 (m,
1H), 1.42–1.29 (m, 2H), 1.11–1.02 (m, 2H), 0.71 (t, J=
7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=173.3, 161.7,
140.9, 138.5, 131.9, 129.6, 129.0, 128.8, 128.6, 128.1, 126.3,
95.2, 68.8, 52.0, 44.9, 40.2, 29.8, 19.6, 13.7; MS (EI): m/z=
394; HR-MS (EI): m/z=394.1714, calcd. for C23H26N2O2S:
394.1715; [a]2D5: À21.9 (c 1.0, CH2Cl2); IR (KBr): n=3027,
2954, 2859, 2359, 1742, 1612 cmÀ1.
dihydro-1H-imidazol-1-yl]-4-methylpentanoate
(7i):
1H NMR (300 MHz, CDCl3): d=7.85–7.71 (m, 3H), 7.69 (s,
1H), 7.54–7.47 (m, 2H), 7.30–7.27 (m, 1H), 7.24–7.19 (m,
3H), 7.07–7.05 (m, 2H), 5.88 (s, 1H), 5.16–4.97 (m, 2H),
3.84–3.80 (m, 1H), 3.76 (s, 3H), 1.93–1.84 (m, 1H), 1.79–
1.71 (m, 1H), 1.69–1.56 (m, 1H), 0.92 (dd, J=8.2, 6.9 Hz,
6H); 13C NMR (75 MHz, CDCl3): d=174.2, 161.4, 140.9,
138.0, 133.2, 132.9, 129.1, 128.5, 128.3, 128.2, 127.8, 127.3,
126.9, 126.9, 126.7, 126.1, 95.9, 65.6, 51.9, 48.7, 43.1, 24.7,
23.4, 21.8; MS (EI): m/z=444; HR-MS (EI): m/z=444.1871,
calcd. for C27H28N2O2S: 444.1871; [a]2D5: À32.7 (c 1.0,
CH2Cl2); IR (KBr): n=2952, 1741, 1615, 1433 cmÀ1.
Methyl (2S)-2-(3-butyl-4-phenyl-2-thioxo-2,3-dihydro-1H-
1
imidazol-1-yl)-3-methylbutanoate (7d): H NMR (300 MHz,
CDCl3): d=7.41–7.36 (m, 3H), 7.35–7.31 (m, 2H), 5.68 (s,
1H), 3.95–3.84 (m, 1H), 3.71 (s, 3H), 3.66–3.57 (m, 1H),
3.39 (d, J=6.3 Hz, 1H), 2.33–2.22 (m, 1H), 1.59–1.37 (m,
2H), 1.16–1.04 (m, 2H), 0.98 (t, J=5.7 Hz, 6H), 0.73 (t, J=
7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=173.6, 161.1,
140.8, 132.2, 128.9, 128.8, 128.6, 94.9, 73.6, 51.6, 44.8, 32.8,
29.9, 19.7, 18.5, 13.7; MS (EI): m/z=346; HR-MS (EI): m/
z=346.1710, calcd. for C19H26N2O2S: 346.1715; [a]2D5: À41.8
(c 1.0, CH2Cl2); IR (KBr): n=2957, 1742, 1615, 1444 cmÀ1.
Methyl (2S)-2-[3-butyl-4-(4-methylphenyl)-2-thioxo-2,3-di-
hydro-1H-imidazol-1-yl]-3-methylbutanoate (7e): 1H NMR
(300 MHz, CDCl3): d=7.18 (s, 4H), 5.16 (s, 1H), 3.90–3.81
(m, 1H), 3.67 (s, 3H), 3.65–3.55 (m, 1H), 3.37 (d, J=6.3 Hz,
1H), 2.35 (s, 3H), 2.29–2.20 (m, 1H), 1.59–1.37 (m, 2H),
1.17–1.03 (m, 2H), 0.97 (t, J=6.6 Hz, 6H), 0.72 (t, J=
7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=173.5, 161.1,
140.8, 138.8, 129.3, 129.3, 128.6, 94.5, 73.5, 51.5, 44.8, 32.8,
29.9, 21.3, 19.7, 18.3, 13.7; MS (EI): m/z=360; HR-MS (EI):
m/z=360.1875, calcd. for C20H28N2O2S: 360.1871; [a]2D5:
À40.2 (c 1.0, CH2Cl2); IR (KBr): n=2957, 1743, 1610, 1509,
1433 cmÀ1.
Methyl
(2S)-2-(3-benzyl-4-phenyl-2-thioxo-2,3-dihydro-
1H-imidazol-1-yl) propanoate (7j): 1H NMR (300 MHz,
CDCl3): d=7.38–7.28 (m, 3H), 7.16–7.14 (m, 5H), 7.02–6.99
(m, 2H), 5.76 (s, 1H), 4.99 (s, 2H), 3.85 (dd, J=13.6, 6.6 Hz,
1H), 3.71 (s, 3H), 1.49 (d, J=6.9 Hz, 3H); 13C NMR
(75 MHz, CDCl3): d=174.2, 161.3, 140.8, 137.7, 131.8, 129.1,
128.9, 128.5, 128.2, 127.5, 127.0, 95.5, 62.3, 51.9, 48.3, 19.1;
MS (EI): m/z=352; HR-MS (EI): m/z=352.1246, calcd. for
C20H20N2O2S: 352.1245; [a]2D5: À47.5 (c 1.0, CH2Cl2); IR
(KBr): n=2948, 1741, 1615, 1444 cmÀ1.
Methyl (2S)-2-[3-benzyl-4-(naphthalen-2-yl)-2-thioxo-2,3-
dihydro-1H-imidazol-1-yl]propanoate
(7k):
1H NMR
(300 MHz, CDCl3): d=7.86–7.71 (m, 3H), 7.66 (s, 1H),
7.55–7.48 (m, 2H), 7.28–7.26 (m, 1H), 7.21–7.19 (m, 3H),
7.08–7.06 (m, 2H), 5.88 (s, 1H), 5.07 (s, 2H), 3.92 (dd, J=
13.4, 6.9 Hz, 1H), 3.76 (s, 3H), 1.55 (d, J=6.9 Hz, 3H);
13C NMR (75 MHz, CDCl3): d=174.2, 161.4, 140.9, 137.8,
133.3, 132.9, 129.1, 128.5, 128.3, 128.2, 127.8, 127.6, 127.1,
126.9, 126.8, 126.2, 95.9, 62.4, 52.0, 48.7, 19.1; MS (EI):
m/z=402; HR-MS (EI): m/z=402.1398, calcd. for
C24H22N2O2S: 402.1402; [a]2D5: À29.4 (c 1.0, CH2Cl2); IR
(KBr): n=2957, 1741, 1615, 1453 cmÀ1.
Methyl (2S)-2-[3-benzyl-4-(4-methylphenyl)-2-thioxo-2,3-
1
dihydro-1H-imidazol-1-yl]-3-methylbutanoate (7f): H NMR
(300 MHz, CDCl3): d=7.37–7.29 (m, 3H), 7.23–7.16 (m,
5H), 7.04–7.02 (m, 2H), 5.77 (s, 1H), 5.11 (d, J=15.6 Hz,
1H), 4.90 (d, J=15.6 Hz, 1H), 3.72 (s, 3H), 3.45 (d, J=
6.3 Hz, 1H), 2.30–2.20 (m, 1H), 0.90 (dd, J=6.7, 3.0 Hz,
6H); 13C NMR (75 MHz, CDCl3): d=173.3, 161.1, 140.7,
137.8, 131.7, 128.9, 128.8, 128.4, 128.0, 127.1, 126.7, 95.2,
73.4, 51.5, 48.3, 32.6, 19.5, 18.2; MS (EI): m/z=380; HR-MS
(EI): m/z=380.1558, calcd. for C22H24N2O2S: 380.1558; [a]25:
À24.3 (c 1.0, CH2Cl2); IR (KBr): n=2957, 1740, 161D7,
1444 cmÀ1.
Methyl (2S)-2-[3-benzyl-4-(biphenyl-4-yl)-2-thioxo-2,3-di-
hydro-1H-imidazol-1-yl]propanoate
(7l):
1H NMR
(300 MHz, CDCl3): d=7.63–7.56 (m, 4H), 7.48 (t, J=
7.2 Hz, 2H), 7.42–7.37 (m, 1H), 7.28–7.23 (m, 5H), 7.13–
7.11 (m, 2H), 5.84 (s, 1H), 5.09 (s, 2H), 3.93 (dd, J=13.5,
6.6 Hz, 1H), 3.76 (s, 3H), 1.56 (d, J=6.6 Hz, 3H); 13C NMR
(75 MHz, CDCl3): d=174.2, 161.3, 141.8, 140.6, 140.1, 137.8,
130.7, 129.3, 129.0, 128.3, 127.9, 127.5, 127.2, 127.1, 95.7,
62.4, 52.0, 48.5, 19.2; MS (EI): m/z=428; HR-MS (EI):
m/z=428.1557, calcd. for C26H24N2O2S: 428.1558; [a]2D5:
À29.4 (c 1.0, CH2Cl2); IR (KBr): n=2948, 1740, 1608,
1453 cmÀ1.
Methyl (2S)-2-[3-benzyl-4-(naphthalen-2-yl)-2-thioxo-2,3-
1
dihydro-1H-imidazol-1-yl]-3-methylbutanoate (7g): H NMR
(300 MHz, CDCl3): d=7.85–7.71 (m, 3H), 7.69 (s, 1H),
7.54–7.48 (m, 2H), 7.31–7.28 (m, 1H), 7.25–7.20 (m, 3H),
7.10–7.08 (m, 2H), 5.87 (s, 1H), 5.17 (d, J=15.6 Hz, 1H),
4.98 (d, J=15.6 Hz, 1H), 3.92 (dd, J=13.4, 6.9 Hz, 1H),
3.76 (s, 3H), 2.38–2.27 (m, 1H), 0.98–0.95 (m 6H);
13C NMR (75 MHz, CDCl3): d=173.5, 161.4, 140.9, 138.1,
133.2, 132.9, 129.2, 128.5, 128.2, 127.8, 127.4, 126.9, 126.9,
126.7, 126.1, 95.8, 73.6, 51.7, 48.8, 32.8, 19.7, 18.5; MS (EI):
m/z=430; HR-MS (EI): m/z=430.1714, calcd. for
C26H26N2O2S: 430.1715; [a]2D5: À20.3 (c 1.0, CH2Cl2); IR
(KBr): n=2957, 1739, 1617, 1453 cmÀ1.
Methyl (2S)-2-(3-butyl-4-phenyl-2-thioxo-2,3-dihydro-1H-
imidazol-1-yl)propanoate
(7m):
1H NMR
(300 MHz,
CDCl3): d=7.41–7.37 (m, 3H), 7.35–7.30 (m, 2H), 5.71 (s,
1H), 3.80–3.67 (m, 3H), 3.72 (s, 3H), 1.49–1.40 (m, 5H),
1.14–1.02 (m, 2H), 0.71 (t, J=7.5 Hz, 3H); 13C NMR
(75 MHz, CDCl3): d=174.4, 161.0, 140.9, 132.2, 128.9, 128.7,
Methyl (2S)-2-(3-butyl-4-phenyl-2-thioxo-2,3-dihydro-1H-
imidazol-1-yl)-4-methylpentanoate
(7h):
1H NMR
194
ꢀ 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2012, 354, 187 – 196