4186
B. C. Ranu, S. S. Dey / Tetrahedron 60 (2004) 4183–4188
1 1
1
colorless oil; IR 3028, 2952, 1675, 1603 cm ; H NMR d
,3-diphenyl-3-(thiobutyl)propan-1-one (315 mg, 92%) as a
2
2869, 1687, 1596 cm2 ; H NMR d 0.84 (t, J¼7.2 Hz, 3H),
1.20–1.57 (m, 4H), 2.26–2.40 (m, 2H), 3.49 (d, J¼7.0 Hz,
2H), 4.52 (t, J¼7.0 Hz, 1H), 7.24–7.57 (m, 7H), 7.89 (d,
1 1
0
2
.82 (t, J¼7.2 Hz, 3H), 1.26–1.34 (m, 2H), 1.39–1.56 (m,
1
3
H), 2.27–2.37 (m, 2H), 3.52 (d, J¼7.0 Hz, 2H), 4.55 (t,
J¼7.8 Hz, 2H); C NMR d 14.0, 22.3, 31.5, 31.6, 43.9,
45.7, 122.9 (2C), 128.9, 129.0, 129.1 (2C), 129.7 (2C),
133.8, 137.0, 141.3, 143.7, 197.1. Anal. calcd for
C H OSCl: C, 68.55; H, 6.36. Found: C, 68.38; H, 6.30.
1
3
J¼7.0 Hz, 1H), 7.17–7.54 (m, 8H), 7.88–7.91 (m, 2H); C
NMR d 14.0, 22.4, 31.5, 31.7, 44.7, 45.9, 127.6, 128.3 (2C),
1
1
28.5 (2C), 128.8 (2C), 128.9, 129.0, 133.6, 137.3, 142.7,
97.4. Anal. calcd for C H OS: C, 76.47; H, 7.43. Found:
C, 76.31; H, 7.28.
1
9 21
1
9 22
4.1.7. 3-(4-Chlorophenyl)-3-(4-chlorothiophenyl)-1-phenyl-
propan-1-one (entry 6, Table 2). White crystal; mp 84–
86 8C; IR (KBr) 3061, 1685, 1473, 688 cm2 ; H NMR d
1 1
The residual ionic liquid was further washed with ether and
after being dried under vacuum was reused for subsequent
reactions. This procedure was followed for all the conjugate
additions listed in Tables 1–3. The known compounds were
identified by comparison of their spectral data with those
3.58 (d, J¼7.1 Hz, 2H), 4.88 (t, J¼7.1 Hz, 1H), 7.16–7.58
1
3
(m, 11H), 7.88 (d, J¼7.8 Hz, 2H); C NMR d 44.8, 48.3,
128.4 (2C), 128.9 (2C), 129.0, 129.1 (2C), 129.4 (2C), 129.5
(2C), 130.8, 133.9, 134.5, 134.8 (2C), 137.5, 140.1, 196.8.
Anal. calcd for C H OSCl : C, 65.12; H, 4.16. Found: C,
4
g,7c,8b,i,10c,12a–d,13
reported,
and the new compounds were
2
1
16
2
1
13
properly characterized by their IR, H NMR and C NMR
spectroscopic data and elemental analyses. These data are
presented below in order of their entries in the Tables 1–3.
64.94; H, 4.04.
4.1.8. 3-(4-Nitrophenyl)-1-phenyl-3-thiobutylpropan-1-
one (entry 7, Table 2). Colorless oil; IR (neat) 2956,
2871, 1687, 1519, 1346 cm2 ; H NMR d 0.84 (t, J¼7.2 Hz,
3H), 1.27–1.36 (m, 2H), 1.44–1.52 (m, 2H), 2.25–2.39 (m,
2H), 3.57 (d, J¼7.1 Hz, 2H), 4.62 (t, J¼7.1 Hz, 1H), 7.41–
C
1 1
4
1
.1.2. 1-Phenyl-3-(thiobutyl)butan-1-one (entry 1, Table
). Colorless oil; IR (neat) 3032, 2929, 1685, 1596 cm21; 1H
NMR d 0.91 (t, J¼7.4 Hz, 3H), 1.35 (d, J¼6.7 Hz, 3H),
1
3
1
2
3
3
.36–1.46 (m, 2H), 1.53–1.64 (m, 2H), 2.57 (t, J¼7.3 Hz,
7.62 (m, 5H), 7.88–7.91 (m, 2H), 8.14–8.17 (m, 2H);
H), 3.05–3.33 (m, 2H), 3.42–3.52 (m, 1H), 7.26–7.59 (m,
NMR d 13.9, 22.3, 31.5, 31.7, 44.1, 45.4, 123.9 (2C), 128.2
(2C), 129.1 (2C), 129.2 (2C), 133.9, 136.7, 147.3, 150.7,
196.6. Anal. calcd for C H O SN: C, 66.45; H, 6.16, N,
1
3
H), 7.90–7.97 (m, 2H); C NMR d 14.1, 22.2, 22.5, 31.0,
2.2, 35.9, 46.6, 128.5 (2C), 129.1 (2C), 133.3, 137.4,
98.7. Anal. calcd for C H OS: C, 71.14; H, 8.53. Found:
1
9 21 3
1
4.08. Found: C, 66.51; H, 6.03, N, 3.92.
1
4 20
C, 70.96; H, 8.45.
4.1.9. 3-(4-Chlorothiophenyl)-3-(4-nitrophenyl)-1-phenyl-
4
(
1
.1.3. 1-Phenyl-3-(4-chlorothiophenyl)butan-1-one
entry 3, Table 1). Colorless oil; IR (neat) 3062, 1681,
propan-1-one (entry 8, Table 2). Yellow crystal; mp 95–
97 8C; IR (KBr) 3058, 1681, 1519, 1346, 688 cm2 ; H
NMR d 3.65 (d, J¼7.1 Hz, 2H), 4.94 (t, J¼7.1 Hz, 1H),
7.15–7.61 (m, 9H), 7.88–7.91 (m, 2H), 8.09–8.12 (m,
1 1
475 cm2 ; H NMR d 1.37 (d, J¼6.7 Hz, 3H), 3.07–3.31
1 1
(m, 2H), 3.85–3.92 (m, 1H), 7.20–7.57 (m, 7H), 7.89–7.91
(m, 2H); C NMR d 21.3, 39.5, 45.7, 128.2 (2C), 128.8
(2C), 129.3 (2C), 133.5, 133.8 (2C), 134.1, 137.8, 147.5,
1
3
13
2H); C NMR d 44.3, 48.5, 124.2 (2C), 128.2 (2C),
128.4, 128.8 (2C), 128.9 (2C), 129.4 (2C), 131.6, 132.2,
134.1, 135.1 (2C), 136.6, 149.3, 196.2. Anal. calcd for
C H O SN: C, 69.60; H, 4.45; N, 3.86. Found: C, 69.80;
198.2. Anal. calcd for C H OSCl: C, 66.08; H, 5.20.
16 15
Found: C, 65.92; H, 5.03.
2
1 16 3
H, 4.26; N, 4.09.
4.1.4. 3-(4-Chlorothiophenyl)-3-(4-methoxyphenyl)-1-
phenylpropan-1-one (entry 3, Table 2). White crystal;
4.1.10. 1-(4-Methylphenyl)-3-phenyl-3-thiobutylpropan-
2
1 1
mp 86–90 8C; IR (KBr) 2947, 1674, 1610 cm ; H NMR d
3
1-one (entry 10, Table 2). White crystal; mp 58 8C; IR
(KBr) 3028, 2952, 1674, 1606 cm2 ; H NMR d 0.83 (t,
J¼7.3 Hz, 3H), 1.26–1.37 (m, 2H), 1.42–1.50 (m, 2H),
2.27–2.36 (m, 2H), 2.37 (s, 3H), 3.47 (d, J¼7.1 Hz, 2H),
4.54 (t, J¼7.1 Hz, 1H), 7.20–7.32 (m, 5H), 7.41 (d, J¼
1 1
.53–3.62 (m, 2H), 3.74 (s, 3H), 4.93 (dd, J ¼6.5 Hz,
1
J ¼7.1 Hz, 1H), 6.79 (d, J¼8.7 Hz, 2H), 7.17–7.54 (m,
2
1
3
9H), 7.89 (d, J¼7.3 Hz, 2H); C NMR d 45.1, 48.4, 55.6,
114.3 (2C), 128.5 (2C), 129.0 (2C), 129.3 (2C), 129.4 (2C),
133.4 (2C), 133.8, 134.1, 134.6 (2C), 137.1, 159.3, 197.3.
1
3
8.2 Hz, 2H), 7.81 (d, J¼8.2 Hz, 2H); C NMR d 14.0, 22.0,
22.3, 31.6, 31.7, 44.8, 45.7, 127.5, 128.2 (2C), 128.6 (2C),
128.9 (2C), 129.7 (2C), 134.8, 142.8, 144.4, 197.0. Anal.
calcd for C H OS: C, 76.88; H, 7.74. Found: C, 77.09; H,
Anal. calcd for C H O SCl: C, 69.01; H, 5.00. Found: C,
2
2 19 2
6
9.24; H, 5.22.
2
0 24
4.1.5. 3-(4-Methoxyphenyl)-1-phenyl-3-thiobutylpro-
pan-1-one (entry 4, Table 2). Colorless oil; IR (neat)
7.69.
2
1 1
3
3
2
1
057, 2835, 1683, 1608 cm ; H NMR d 0.84 (t, J¼7.2 Hz,
H), 1.26–1.35 (m, 2H), 1.43–1.54 (m, 2H), 2.24–2.38 (m,
H), 3.50 (d, J¼7.1 Hz, 2H), 3.77 (s, 3H), 4.52 (t, J¼7.1 Hz,
H), 6.84 (d, J¼7.4 Hz, 2H), 7.26–7.56 (m, 5H), 7.90 (d,
4.1.11. 3-(3-Acetoxyphenyl)-1-phenyl-3-thiobutylpro-
pan-1-one (entry 11, Table 2). Colorless oil; IR (neat)
3024, 2952, 1764, 1675, 1604 cm2 ; H NMR d 0.82 (t,
J¼7.2 Hz, 3H), 1.26–1.34 (m, 2H), 1.39–1.56 (m, 2H),
2.15 (s, 3H), 2.27–2.37 (m, 2H), 3.52 (d, J¼7.0 Hz, 2H),
4.55 (t, J¼7.0 Hz, 1H), 6.89–7.54 (m, 7H), 7.89 (d,
1 1
1
3
J¼7.4 Hz, 2H); C NMR d 14.1, 22.4, 31.5, 31.7, 44.1,
4
1
5.9, 55.6, 114.2, 114.3, 128.5 (2C), 129.0 (2C), 129.2,
29.3, 133.6, 134.6, 137.2, 158.9, 197.6. Anal. calcd for
1
3
J¼8.3 Hz, 2H); C NMR d 14.0, 21.2, 22.4, 31.5,
C H O S: C, 73.13; H, 7.36. Found: C, 73.01; H, 7.21.
20 24 2
31.7, 44.7, 45.9, 127.6, 128.3 (2C), 128.5, 128.8 (2C),
128.9, 129.0, 133.6, 137.3, 142.7, 157.3, 169.2, 197.4.
Anal. calcd for C H O S: C, 70.76; H, 6.79. Found: C,
70.58; H, 6.89.
4
1
.1.6. 3-(4-Chlorophenyl)-1-phenyl-3-thiobutylpropan-
-one (entry 5, Table 2). Colorless oil; IR (neat) 2956,
2
1 24 3