10.1002/ejoc.201700654
European Journal of Organic Chemistry
FULL PAPER
7.69 (d, J = 8.3 Hz, 2H), 7.53 (dd, J = 7.5 1.5 z 1 ) 7.35−7.27 ( 5 )
7.22 (dt, J = 7.8 1.8 z 1 ) 7.18−7.12 ( 2 ) 6.99−6.91 ( 1 ) 6.80
(d, J = 8.3 Hz, 1H), 5.13 (t, J = 7.5 Hz, 1H), 4.44 (d, J = 8.3 Hz, 1H),
4.09−3.93 ( 3 ) 3.62 (d J = 13.1 Hz, 1H), 3.40 (dd, J = 9.9, 7.7Hz,
1H), 3.35 (d, J = 13.1 Hz, 1H), 2.62 (dd, J = 10.4, 7.9Hz, 1H), 2.48 (s,
3H), 1.41 (t, J = 6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 155.7 143.3
137.9, 135.2, 129.4, 128.8, 128.6, 128.4, 128.3, 127.9, 127.7, 127.4,
120.5, 111.0, 71.0, 63.4, 60.7, 57.5, 57.2, 21.6, 15.0; HRMS: calcd for
C25H29N2O3S [M+H]+ 437.1899, found 437.1893; IR (KBr): 2953, 2858,
4-(4-Methoxyphenyl)-1-phenethyl-3-tosylimidazolidine (3be): Light
yellow solid; mp. 91-93 °C; Yield 88% (57 mg); 1H NMR (400 MHz,
CDCl3): δ 7.84 (d, J = 8.3 z 1 ) 7.70−7.64 ( J = 8.0 Hz, 2H),
7.37−7.21 ( 5 ) 7.15 (d J = 7.3 z 3 ) 6.91−6.83 ( J = 8.3 Hz,
2H), 4.66 (t, J = 7.2 Hz, 1H), 4.51 (d, J = 7.5 Hz, 1H), 4.22 (d, J = 7.5 Hz,
1H), 3.83 (s, 3H), 3.23 (dd, J = 10.2 6.9 z 1 ) 2.74−2.48 ( 5 )
2.43 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 159.1 146.5 143.6 139.4
135.0, 132.6, 129.7, 129.6, 128.6, 128.4, 128.2, 127.9, 127.7, 126.4,
113.9, 71.4, 62.9, 61.3, 55.3, 54.8, 35.1, 21.6; HRMS: calcd for
C25H29N2O3S [M+H]+ 437.1899, found 437.1907; IR (KBr): 2925, 2854,
1456, 1162 cm−1
.
1513, 1304, 1160 cm−1
.
1-(3-Methoxybenzyl)-4-phenyl-3-tosylimidazolidine (3ab): Off-white
solid; mp. 85-87 °C; Yield 85% (54 mg); 1H NMR (400 MHz, CDCl3): δ
7.65 (d, J = 8.0 z 2 ) 7.19−7.41 ( 8 ) 6.81−6.86 (m, 1H),
6.74−6.79 ( 2 ) 4.77 ( J = 7.4 Hz, 1H), 4.47 (d, J = 8.0 Hz, 1H), 4.14
(d, J = 8.0 Hz, 1H), 3.81 (s, 3H), 3.58 (d, J = 13.3 Hz, 1H), 3.42 (d, J =
13.1 Hz, 1H), 3.28 (dd, J = 10.2, 7.2 Hz, 1H), 2.69 (dd, J = 10.4, 7.7 Hz,
1 ) 2.42−2.48 ( 3H); 13C NMR (100 MHz, CDCl3): δ 159.8 143.6
140.7, 139.2, 135.1, 129.6, 129.4, 128.5, 128.5, 127.8, 127.5, 126.6,
120.7, 114.1, 112.8, 71.4, 62.4, 61.9, 57.0, 55.2, 21.5; HRMS: calcd for
C24H27N2O3S [M+H]+ 423.1742, found 423.1749; IR (KBr): 2924, 2853,
1-Phenethyl-4-(p-tolyl)-3-tosylimidazolidine (3ce): Light yellow solid;
mp. 99-101 °C; Yield 81% (51 mg); 1H NMR (400 MHz, CDCl3): δ 7.67 (d
J = 8.3 z 2 ) 7.33−7.22 ( 7 ) 7.17−7.08 ( 4 ) 4.64 ( J = 7.2 Hz,
1H), 4.51 (d, J = 7.5 Hz, 1H), 4.21 (d, J = 7.8 Hz, 1H), 3.24 (dd, J = 10.2,
7.4 z 1 ) 2.76−2.67 ( 3 ) 2.65−2.47 ( 2 ) 2.42 ( 3 ) 2.36 (
3H); 13C NMR (100 MHz, CDCl3): δ 143.5 139.4 137.6 134.9 129.6
129.2, 128.6, 128.4, 127.7, 126.6, 126.3, 71.6, 63.0, 61.5, 54.9, 35.1,
21.6, 21.2; HRMS: calcd for C25H29N2O2S [M+H]+ 421.1950, found
421.1955; IR (KBr): 3027, 2924, 2853, 1598, 1454, 1161 cm−1
.
1599, 1455, 1350, 1161 cm−1
.
4-(2-Ethoxyphenyl)-1-phenethyl-3-tosylimidazolidine (3ee):
1-(3-Methoxybenzyl)-4-(4-methoxyphenyl)-3-tosyl
imidazolidine
(3bb): Light yellow solid; mp. 92-94 °C; Yield 89% (60 mg); 1H NMR (400
MHz, CDCl3): δ 7.67 (d J = 8.0 z 2 ) 7.37−7.27 ( 3 ) 7.19 (d J =
7.5 Hz, 2H), 7.23 (d, J = 8.3 z 2 ) 6.92−6.82 ( 2 ) 6.80−6.73 (
1H), 4.74 (t, J = 7.3 Hz, 1H), 4.46 (d, J = 7.8 Hz, 1H), 4.14 (d, J = 7.8 Hz,
1H), 3.82 (s, 6H), 3.59 (d, J = 13.1 Hz, 1H), 3.42 (d, J = 13.1 Hz, 1H),
3.25 (dd, J = 10.0, 7.0Hz, 1H), 2.69 (dd, J = 10.2, 7.9 Hz, 1H), 2.47 (s,
3H); 13C NMR (100 MHz, CDCl3): δ 158.7 158.0 142.4 138.2 134.0
131.6, 128.5, 128.3, 127.1, 126.8, 126.7, 125.3, 119.7, 113.0, 112.8,
70.2, 61.3, 60.5, 55.9, 54.2, 54.1, 20.5; HRMS: calcd for C25H29N2O4S
[M+H]+ 453.1848, found 453.1852; IR (KBr): 2957, 2926, 2854, 1599,
Transparent oil; Yield 76% (49 mg); 1H NMR (400 MHz, CDCl3): δ 7.71 (d
J = 8.3 Hz, 2H), 7.51 (dd, J = 7.5 1.5 z 1 ) 7.31−7.20 ( 6 )
7.15−7.09 ( 2 ) 6.94 (d J = 7.5, 0.9Hz, 1H), 6.80 (d, J = 7.5 Hz, 1H),
5.06 (t, J = 7.3 Hz, 1H), 4.53 (d, J = 7.8 Hz, 1H), 4.17 (d, J = 8.0 Hz, 1H),
4.07−3.99 ( 2H), 3.34 (dd, J = 9.9 7.4 z 1 ) 2.73−2.55 ( 4 )
2.54−2.46 ( 1 ) 2.46−2.38 ( 3 ) 1.42 ( J = 7.0 Hz, 3H); 13C NMR
(100 MHz, CDCl3): δ 155.7 143.4 139.5 129.4 128.6 128.4 128.3
127.8, 126.2, 120.5, 111.0, 71.3, 63.4, 61.3, 57.1, 55.0, 35.2, 21.6,
15.0;HRMS: calcd for C26H30N2O3S [M]+ 450.1977, found 450.1987; IR
(Neat): 2927, 2854, 1599, 1348, 1160 cm−1
.
1455, 1348, 1160 cm−1
.
1-Benzyl-3-(benzylsulfonyl)-4-phenylimidazolidine (3fa): Light brown
oil; Yield 66% (38 mg); 1H NMR (400 MHz, CDCl3): δ 7.29−7.44 ( 15 )
4.98 (t, J= 7.5 Hz, 1H), 4.38 (dd, J = 8.2 1.4 z 1 ) 4.02−4.09 ( 1 )
3.85−3.96 ( 2 ) 3.69 (d J = 2.0 Hz, 2H), 3.46 (ddd, J = 10.9, 7.2, 1.5
z 1 ) 2.86−2.93 ( 1 ); 13C NMR (100 MHz, CDCl3): δ 140.5, 137.6,
130.8, 128.9, 128.8, 128.5, 128.0, 127.5, 127.1, 125.6, 71.5, 62.4, 61.3,
59.1, 57.2; HRMS: calcd for C23H25N2O2S [M+H]+ 393.1637, found
1-(3-Methoxybenzyl)-4-(p-tolyl)-3-tosylimidazolidine (3cb): Off-white
solid; mp. 75-77 °C; Yield 84% (55 mg); 1H NMR (400 MHz, CDCl3): δ
7.69−7.61 ( 2 ) 7.33−7.28 ( 2 ) 7.24 (dd J = 8.0, 6.5 Hz, 3H),
7.13 (d, J = 7.8 Hz, 2H), 6.82 (ddd, J = 8.3 2.4 1.0 z 1 ) 6.77−6.71
(m, 2H), 4.71 (t, J = 7.4 Hz, 1H), 4.45 (d, J = 8.0 Hz, 1H), 4.11 (d, J = 8.0
Hz, 1H), 3.81 (s, 3H), 3.56 (d, J = 13.1 Hz, 1H), 3.39 (d, J = 13.1 Hz, 1H),
3.26 (dd, J = 7.4, 9.9 Hz, 1H), 2.67 (dd, J = 10.4, 7.9Hz, 1H), 2.47 (s, 3H),
2.35 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 159.7 143.5 139.2 137.6
137.2, 135.0, 129.5, 129.4, 129.2, 127.8, 126.5, 120.7, 114.1, 112.8,
71.4, 62.4, 61.8, 57.0, 55.2, 21.6, 21.1; HRMS: calcd for C25H29N2O3S
[M+H]+ 437.1899, found 437.1898; IR (Kbr): 2957, 2924, 2854, 1598,
393.1633; IR (Neat): 2927, 2853, 1598, 1351, 1160cm−1
.
1-Benzyl-3-((3-fluorophenyl)sulfonyl)-4-phenylimidazolidine
(3ga):
1
Light brown solid; mp. 96-98 °C; Yield 42% (71 mg); H NMR (400 MHz,
CDCl3): δ 7.51-7.49 (m, 1H), 7.46-7.42 ( 1 ) 7.39−7.34 ( 3 )
7.32−7.26 ( 8 ) 7.21−7.20 ( 1 ) 5.16 (dd J = 6.5, 4.3Hz, 1H), 4.44
(d, J = 7.3 Hz, 1H), 4.23 (d, J = 7.0 Hz, 1H), 3.77 ( 2 ) 3.53−3.46 (
1H), 3.22 (dd, J = 11.0, 4.0Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 163.5
161.0, 140.4, 139.9, 137.4, 130.6, 128.6, 127.7, 126.6, 125.8, 123.4,
119.9, 115.1, 71.4, 62.5, 61.9, 57.1; HRMS: calcd for C22H22FN2O2S
[M+H]+ 397.1386, found 397.1389; IR (KBr): 2924, 2852, 1591, 1474,
1455, 1350, 1161 cm−1
.
(R)-1-((R)-1-(3-Methoxyphenyl)ethyl)-4-phenyl-3-tosyl imidazolidine
(3ad) (1:1 mixture of diastereomers): Transparent oil; Yield 76% (49
mg); 1H NMR (400 MHz, CDCl3): δ 7.72 (d, J = 8.3 Hz, 2H), 7.64 (d, J =
8.3 z 2 ) 7.42−7.37 ( 2 ) 7.37−7.23 ( 13 ) 7.23−7.16 ( 2 )
6.84−6.75 ( 2 ) 6.74−6.61 ( 4 ) 4.74−4.65 ( 2 ) 4.56 (d J =
7.3 Hz, 1H), 4.30 (d, J = 7.5 Hz, 1H), 3.97 (dd, J = 7.4, 14.7 Hz, 2H), 3.77
(s, 3H), 3.80 (s, 3H), 3.17 (dd, J = 19.8,6.3 Hz, 2H), 3.02 (s, 1H), 2.48 (d,
J = 3.8 z 6 ) 2.46−2.38 ( 2 ) 1.28−1.27 ( 6 ); 13C NMR (100
MHz, CDCl3): δ 159.8 159.7 145.7 145.6 143.6 143.6, 140.8, 140.8,
134.8, 134.6, 129.6, 129.5, 129.5, 129.5, 128.4, 128.4, 128.0, 127.6,
127.5, 126.6, 126.5, 119.1, 112.6, 112.5, 112.4, 70.6, 69.9, 62.8, 62.5,
62.1, 61.9, 60.6, 60.4, 55.2, 55.1, 22.8, 22.8, 21.6, 21.5; HRMS: calcd for
C25H29N2O3S [M+H]+ 437.1899, found 437.1903; IR (Neat): 2925, 2853,
1356, 1156 cm−1
.
N-(2-(Benzylamino)-1-(p-tolyl)ethyl)-4-methylbenzene sulfonamide
(6a): Transparent sticky oil; Yield 88% (35 mg); 1H NMR (400 MHz,
CDCl3): δ 7.61−7.56 ( 2 ) 7.37−7.25 ( 3 ) 7.25−7.21 ( 2 ),
7.19−7.11 ( 2 ) 7.10−7.00 ( 4 ) 4.29 (dd J = 5.0, 7.3 Hz, 1 H),
3.63 ( 2 ) 2.82−2.70 ( 2 ) 2.38 ( 3 ) 2.31 ( 3 ); 13C NMR
(100 MHz, CDCl3): δ 143.1 139.6 137.3 136.3 129.4 129.1 128.5
128.1, 127.3, 127.2, 126.7, 56.4, 54.1, 53.0, 21.5, 21.1; HRMS: calcd for
1597, 1348, 1162 cm−1
.
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