9370
F.-T. Luo et al. / Tetrahedron 62 (2006) 9365–9372
251. HRMS calcd for C20H23N2O2: 323.1760; found:
323.1755.
4.2.14. 2-[(8-Chloro-2-phenyl(4-quinolyl))amino]-2-
methylpropan-1-ol (8j). Yield: 83%. 1H NMR (CDCl3,
TMS) d 1.53 (s, 6H), 3.76 (s, 2H), 7.16 (s, 1H), 7.29 (t,
J¼8.0 Hz, 1H), 7.44–7.54 (m, 3H), 7.73–7.78 (m, 2H),
8.13 (d, J¼7.6 Hz, 2H) ppm. 13C NMR (CDCl3, TMS)
d 23.41, 55.68, 70.05, 99.39, 119.74, 120.06, 124.44,
127.48, 128.95, 129.86, 130.06, 132.57, 139.09, 143.23,
150.28, 156.54 ppm. IR (KBr) n 3387, 1583, 1528,
694 cmꢀ1. MS m/z 326 (M+), 295, 245. HRMS calcd for
C19H19N2OCl: 326.1186; found: 326.1190.
4.2.9. 2-Methyl-2-{[2-(3-methylphenyl)(4-quinolyl)]-
amino}propan-1-ol (8e). Yield: 82%. Mp 132–134 ꢂC.
1H NMR (CDCl3, TMS) d 1.47 (s, 6H), 2.44 (s, 3H), 3.70
(s, 2H), 6.90 (s, 1H), 7.23 (d, J¼7.6 Hz, 1H), 7.30 (t,
J¼7.6 Hz, 1H), 7.35 (t, J¼7.6 Hz, 1H), 7.55–7.61 (m, 2H),
7.67 (d, J¼7.9 Hz, 1H), 8.06 (d, J¼7.9 Hz, 1H) ppm. 13C
NMR (CDCl3, TMS) d 21.56, 23.90, 55.02, 69.14, 99.19,
118.70, 119.44, 124.52, 124.70, 128.26, 128.48, 129.23,
129.39, 129.82, 138.25, 140.28, 148.04, 148.82,
157.71 ppm. IR (KBr) n 3395, 1587, 1528 cmꢀ1. MS m/z
307 (M++H), 275, 235. HRMS calcd for C20H23N2O:
307.1810; found: 307.1808.
4.2.15. (2R)-2-{[2-(2-Hydroxyphenyl)(4-quinolyl)]-
amino}-2-phenylethan-1-ol (8k). Yield: 75%. 1H NMR
(CDCl3, TMS) d 3.88 (dd, J¼7.4, 11.4 Hz, 1H), 4.11 (dd,
J¼3.8, 11.4 Hz, 1H), 4.52 (t, J¼3.8 Hz, 1H), 6.47 (s, 1H),
6.81 (t, J¼7.9 Hz, 1H), 7.01 (d, J¼7.9 Hz, 1H), 7.26–7.36
(m, 7H), 7.52 (t, J¼8.0 Hz, 2H), 7.70 (d, J¼8.0 Hz, 1H),
7.80 (d, J¼8.0 Hz, 1H) ppm. 13C NMR (CDCl3, TMS)
d 59.42, 66.91, 95.39, 117.34, 117.91, 118.70, 118.94,
119.43, 124.97, 126.33, 126.46, 126.92, 128.20, 129.16,
130.04, 131.72, 138.29, 143.48, 149.89, 157.45,
162.30 ppm. IR (KBr) n 3365, 1594 cmꢀ1. MS m/z 357
(M++H), 356, 237. HRMS calcd for C23H21N2O2:
357.1603; found: 357.1610.
4.2.10. 2-{[2-(4-Bromophenyl)(4-quinolyl)]amino}-2-
1
methylpropan-1-ol (8f). Yield: 84%. Mp 171–174 ꢂC. H
NMR (CDCl3, TMS) d 1.50 (s, 6H), 3.75 (s, 2H), 6.90 (s,
1H), 7.36 (t, J¼7.6 Hz, 1H), 7.58–7.64 (m, 4H), 7.81–7.83
(m, 2H), 8.03 (d, J¼8.4 Hz, 1H) ppm. 13C NMR (CDCl3,
TMS) d 24.11, 55.06, 68.52, 98.37, 118.69, 119.29,
123.36, 124.70, 129.04, 129.28, 129.68, 131.65, 139.30,
148.39, 148.66, 156.29 ppm. IR (KBr) n 3395, 1587,
1532 cmꢀ1. MS m/z 373, 371 (M++H), 339, 299. HRMS
calcd for C19H20N2OBr: 371.0759; found: 371.0753.
4.2.16. 2-{(1E)-2-Aza-2-[3-(4,4-dimethyl(1,3-oxazolin-2-
yl))phenyl]-1-methylvinyl}phenol (4). Yield: 86%. Yellow
oil. 1H NMR (CDCl3, TMS) d 1.39 (s, 6H), 2.34 (s, 3H), 4.13
(s, 2H), 6.89 (t, J¼7.6 Hz, 1H), 7.00–7.02 (m, 2H), 7.37 (t,
J¼7.9 Hz, 1H), 7.43 (t, J¼7.9 Hz, 1H), 7.52 (s, 1H), 7.62
(d, J¼7.9 Hz, 1H), 7.77 (d, J¼7.9 Hz, 1H) ppm. 13C NMR
(CDCl3, TMS) d 17.27, 28.38, 67.65, 79.25, 118.19, 118.26,
119.62, 120.97, 124.03, 124.60, 128.95, 129.02, 129.12,
133.18, 147.23, 161.74, 161.87, 171.70 ppm. IR (KBr)
n 1644, 1610 cmꢀ1. MS m/z 308 (M+), 307, 293. HRMS calcd
for C19H20N2O2: 308.1525; found: 308.1523.
4.2.11. 2-{[2-(4-Fluorophenyl)(4-quinolyl)]amino}-2-
1
methylpropan-1-ol (8g). Yield: 82%. Mp 176–178 ꢂC. H
NMR (CDCl3, TMS) d 1.49 (s, 6H), 3.73 (s, 2H), 6.85 (s,
1H), 7.14 (t, J¼8.6 Hz, 2H), 7.34 (t, J¼7.6 Hz, 1H), 7.55
(d, J¼8.4 Hz, 1H), 7.61 (t, J¼7.6 Hz, 1H), 7.88–7.91 (m,
2H), 8.02 (d, J¼8.4 Hz, 1H) ppm. 13C NMR (CDCl3,
TMS) d 24.03, 55.16, 68.63, 98.45, 115.37, 115.59,
118.48, 119.45, 124.64, 129.15, 129.31, 129.39, 136.11,
147.83, 148.91, 156.19, 162.31, 164.79 ppm. IR (KBr)
n 3395, 1587, 1532, 1510, 1226, 828 cmꢀ1. MS m/z 311
(M++H), 279, 239. HRMS calcd for C19H20N2OF:
311.1560; found: 311.1564.
4.2.17. 2-{(1E)-2-Aza-2-[4-(4,4-dimethyl(1,3-oxazolin-2-
yl))phenyl]-1-methylvinyl}phenol (5). Yield: 74%. Yellow
oil. 1H NMR (CDCl3, TMS) d 1.36 (s, 6H), 2.28 (s, 3H), 4.09
(s, 2H), 6.84–6.91 (m, 3H), 6.98 (d, J¼7.8 Hz, 1H), 7.34 (t,
J¼7.8 Hz, 1H), 7.58 (d, J¼7.8 Hz, 1H), 7.93–7.95 (m,
2H) ppm. 13C NMR (CDCl3, TMS) d 17.20, 28.37, 67.53,
76.68, 79.11, 118.23, 119.54, 121.08, 124.59, 128.92,
129.21, 133.25, 149.71, 161.72, 161.73, 171.33 ppm. IR
(KBr) n 1645, 1608, 1574 cmꢀ1. MS m/z 308 (M+), 307,
293, 221. HRMS calcd for C19H20N2O2: 308.1525; found:
308.1523.
4.2.12. 2-Methyl-2-[(2-phenyl(4-quinolyl))amino]pro-
pan-1-ol (8h). Yield: 88%. Mp 168–170 ꢂC. 1H NMR
(CDCl3, TMS) d 1.52 (s, 6H), 3.75 (s, 2H), 7.01 (s, 1H),
7.37 (t, J¼7.6 Hz, 1H), 7.41–7.51 (m, 3H), 7.60–7.65 (m,
2H), 7.97–7.99 (m, 2H), 8.05 (d, J¼7.9 Hz, 1H) ppm. 13C
NMR (CDCl3, TMS) d 24.03, 54.96, 68.64, 98.97, 118.72,
119.29, 124.49, 127.56, 128.55, 128.89, 129.09, 129.71,
140.56, 148.45, 148.54, 157.68 ppm. IR (KBr) n 3395,
1587 cmꢀ1. MS m/z 293 (M++H), 261, 221. HRMS calcd
for C19H21N2O: 293.1655; found: 293.1654.
4.2.18. 2-{(1E)-2-Aza-2-[2-(4,4-dimethyl(1,3-oxazolin-2-
yl))phenyl]-1-phenylvinyl}phenol (7). Yield: 82%. Yellow
solid.19 Mp 107–109 ꢂC (recrystallization from ethanol). 1H
NMR (CDCl3, TMS) d 1.36 (s, 6H), 4.08 (s, 2H), 6.55 (d,
J¼7.5 Hz, 1H), 6.74 (t, J¼7.5 Hz, 1H), 7.01 (t, J¼7.5 Hz,
1H), 7.04–7.09 (m, 2H), 7.12 (t, J¼7.7 Hz, 1H), 7.19–7.22
(m, 2H), 7.26–7.28 (m, 3H), 7.36 (t, J¼7.7 Hz, 1H), 7.77
(d, J¼7.7 Hz, 1H) ppm. 13C NMR (CDCl3, TMS) d 28.21,
67.19, 79.45, 117.86, 117.92, 120.13, 122.43, 124.09,
127.98, 128.32, 128.39, 128.82, 129.13, 130.01, 131.04,
132.29, 133.12, 134.45, 147.15, 162.10, 172.51 ppm.
IR (KBr) n 1645, 1607, 1569 cmꢀ1. MS m/z 371 (M++H),
299, 191, 190, 119. HRMS calcd for C24H23N2O2:
371.1760; found: 371.1758.
4.2.13. 2-Methyl-2-[(2-naphthyl(4-quinolyl))amino]pro-
pan-1-ol (8i). Yield: 86%. Mp 162–164 ꢂC. 1H NMR
(CDCl3, TMS) d 1.57 (s, 6H), 3.82 (s, 2H), 7.18 (s, 1H),
7.39 (t, J¼7.1 Hz, 1H), 7.50–7.52 (m, 2H), 7.63–7.69 (m,
2H), 7.89–7.90 (m, 1H), 7.96–7.98 (m, 2H), 8.11 (d,
J¼7.1 Hz, 1H), 8.18 (d, J¼8.4 Hz, 1H), 8.45 (s, 1H) ppm.
13C NMR (CDCl3, TMS) d 24.16, 55.09, 68.44, 99.03,
118.74, 119.31, 124.56, 125.28, 126.12, 126.46, 126.80,
127.62, 128.21, 128.85, 129.14, 129.59, 133.32, 133.66,
137.71, 148.57, 157.33 ppm. IR (KBr) n 3395, 1583,
1528 cmꢀ1. MS m/z 343 (M++H), 271. HRMS calcd for
C23H23N2O: 343.1810; found: 343.1804.