Organic & Biomolecular Chemistry
DOI: 10.1039/C4OPB0a2g59e7K10 of 16
Organic & Biomolecular Chemistry
PAPER
(2-(Dimethylamino)-4-(piperidin-1-yl)phenyl)(pyridin-2-
yl)methanol (12b)
7.12-7.08 (m, 1H), 6.03 (s, 1H) 5.34 (br s, 1H); 13C NMR
(CDCl3, 100 MHz): δ 159.8, 148.1, 141.2, 137.7, 137.5, 137.1,
125.1, 124.5, 124.2, 123.0, 122.9, 122.8, 121.4, 71.0.
292 mg, (94%) of 12b as yellow oil; IR (KBr cm-1): 3468,
1
2932, 2852, 2793, 1604, 1507, 1228, 1011; H NMR (CDCl3,
(4-(Methylamino)-2-nitrophenyl)(pyridin-2-yl)methanol
(17b)
400 MHz): δ 8.54-8.52 (m, 1H), 7.64 (td, J = 7.6, 1.6 Hz, 1H),
7.46 (d, J = 7.6, 1.6 Hz, 1H), 7.13-7.10 (m, 1H), 6.98 (d, J =
8.4 Hz, 1H), 6.55 (d, J = 2.8 Hz, 1H), 6.47 (dd, J = 7.6, 2.8 Hz,
1H), 6.023 (s, 1H), 2.91 (s, 6H), 2.85-2.83 (m, 4H), 1.73-1.67
(m, 4H), 1.56 (br s, 2H); 13C NMR (CDCl3, 100 MHz): δ 163.9,
152.8, 150.7, 148.2, 136.5, 129.9, 126.2, 121.7, 120.8, 109.5,
o
159 mg, (72%) of 17b as yellow solid, m.p. 87 C; IR (KBr
cm-1): 3384, 3141, 2918, 2852, 1632, 1569, 1523, 1172, 1044,
1
760; H NMR (CDCl3, 400 MHz): δ 8.57 (d, J = 4.8 Hz, 1H),
8.20 (d, J = 2.0 Hz, 1H), 8.07 (br s, 1H), 7.67 (td, J = 8.0, 2.0
Hz, 1H), 7.46 (dd, J = 8.8, 2.0 Hz, 1H), 7.24-7.21 (m, 1H), 7.15
(d, J = 8.0 Hz, 1H), 6.82 (d, J = 8.8 Hz, 1H), 5.68 (s, 1H), 5.31
(br s, 1H), 3.01 (d, J = 5.2 Hz, 1H); 13C NMR (CDCl3, 100
MHz): δ 160.3, 148.0, 146.2, 137.2, 135.3, 130.5, 125.4, 122.8,
121.4, 114.2, 73.9, 29.9. HRMS-ESI (m/z): Calculated for
C13H13N3O3 (M+H); 260.1029 Found: 260.1024
105.9, 74.7, 54.8, 40.7, 26.7, 24.1.
HRMS-ESI (m/z):
Calculated for C19H25N3O (M+H); 312.2076 Found: 312.2066.
(1-(Allyloxy)naphthalen-2-yl)(pyridin-2-yl)methanol (13b)
227 mg, (78%) of 13b as yellow solid; m.p. 78 ºC; IR (KBr
cm-1): 3210, 2858, 2743, 1968, 1880, 1857, 1593, 1511, 1155,
1085, 934, 808; 1H NMR (CDCl3, 400 MHz): δ 8.54 (d, J = 4.8
Hz, 1H), 8.37-8.35 (m, 1H), 8.03-8.01 (m, 1H), 7.54 (t, J = 7.6
Hz, 1H), 7.45-7.43 (m, 2H), 7.35 (d, J = 8.0 Hz, 1H), 7.21-7.18
(m, 1H), 7.05 (d, J = 8.0 Hz, 1H), 6.76 (d, J = 7.6 Hz, 1H),
6.31 (s, 1H), 6.22-6.21 (m, 1H), 5.52 (d, J = 17.2 Hz, 1H), 5.34
(d, J = 10.4 Hz, 1H), 4.71 (d, J = 4.8 Hz, 2H); 13C NMR
(CDCl3, 100 MHz): δ 161.4, 154.7, 147.9, 136.9, 133.3, 132.3,
130.4, 126.8, 126.7, 126.5, 125.1, 124.3, 122.8, 122.4, 121.5,
117.5, 104.3, 73.7, 69.0. HRMS-ESI (m/z): Calculated for
C19H17NO2 (M+H); 292.1332 Found: 292.1328.
Benzofuran-3-yl(pyridin-2-yl)methanol2 (18b)
163 mg, (72%) of 18b as yellow oil; IR (KBr cm-1): 3350,
3097, 2978, 1584, 1441, 1148, 1350, 1097, 842; 1H NMR
(CDCl3, 400 MHz): δ 8.61 (d, J = 4.8 Hz, 1H), 7.73 (td, J =
7.6, 1.6 Hz, 1H), 7.53-7.51 (m, 1H), 7.44-7.38 (m, 2H), 7.29-
7.26 (m, 1H), 7.24-7.17 (m, 2H), 6.69 (s, 1H), 6.68 (s, 1H),
5.93 (br s, 1H); 13C NMR (CDCl3, 100 MHz): δ 157.9, 157.4,
155.3, 148.2, 137.2, 128.2, 124.3, 123.3, 122.9, 121.6, 121.2,
111.4, 104.2, 69.2. HRMS-ESI (m/z): Calculated for C14H11NO2
(M+H); 226.0859 Found: 226.0858.
(5-Methyl-2-(prop-2-yn-1-yloxy)phenyl)(pyridin-2-yl)methanol
(14b)
(5-Methyl-2-((5-(p-tolyloxy)pentyl)oxy)phenyl)(pyridin-2-
yl)methanol (19b)
201 mg, (79%) of 14b as yellow oil; IR (KBr cm-1): 3422,
3292, 2922, 2858, 2122, 1594, 1498, 1238, 1034, 673; 1H NMR
(CDCl3, 400 MHz): δ 8.54 (d, J = 4.8 Hz, 1H), 7.60 (td, J =
8.0, 2.0 Hz, 1H), 7.33 (d, J = 8.0 Hz, 1H), 7.18-7.15 (m, 2H),
7.03 (dd, J = 8.4, 1.6 Hz, 1H), 6.90 (d, J = 8.4 Hz, 1H), 4.72 (d,
J = 2.4 Hz, 1H), 2.49 (t, J = 2.4 Hz, 1H), 2.24 (s, 3H); 13C
NMR (CDCl3, 100 MHz): 161.1, 152.7, 147.7, 136.9, 132.3,
131.5, 129.1, 128.5, 122.3, 121.5, 112.7, 78.8, 75.5, 68.9, 56.6,
20.7. HRMS-ESI (m/z): Calculated for C16H15NO2 (M+H);
254.1176 Found: 254.1176.
289 mg, (73%) of 19b as colorless oil; IR (KBr cm-1):3415,
2922, 1597, 1513, 1242, 816, 509; 1H NMR (CDCl3, 400
MHz): δ 8.52 (d, J = 4.8 Hz, 1H), 7.56 (td, J = 7.6, 1.6 Hz,
2H), 7.28 (d, J = 8.0 Hz, 1H), 7.14-7.12 (m, 2H), 7.06 (d, J =
8.0 Hz, 2H), 7.02 (dd, J = 8.4, 1.6 Hz, 1H), 6.78-6.76 (m, 3H),
6.14 (s, 1H), 5.22 (br s 1H), 4.05-4.01 (m, 1H), 3.96-3.90 (m,
3H), 2.27 (s, 3H), 2.23 (s, 3H), 1.84-1.77 (m, 4H), 1.59-1.58
(m, 2H); 13C NMR (CDCl3, 100 MHz): δ 161.5, 157.0, 154.0,
147.7, 136.7, 131.4, 130.1, 129.9, 129.8, 129.1, 128.6, 122.2,
121.3, 114.4, 111.7, 697, 68.22, 67.8, 29.2, 29.1, 22.9, 20.7,
20.5. HRMS-ESI (m/z): Calculated for C25H29NO3 (M+H);
(5-Bromothiophen-2-yl)(pyridin-2-yl)methanol (15b)
392.2220 Found: 392.2211
.
o
195 mg, (73%) of 15b as black solid; m.p. 63 C; IR (KBr
cm-1): 3397, 2942, 2839, 1598, 1468, 1436, 1130, 1098, 1037,
754; H NMR (CDCl3, 400 MHz): δ 8.57 (d, J = 4.8 Hz, 1H),
((Pentane-1,5-diylbis(oxy))bis(5-methyl-2,1-
phenylene))bis(pyridin-2-ylmethanol) (20b)
1
7.73-7.68 (td, J = 8.0, 1.6 Hz, 1H), 7.29-7.25 (m, 2H), 6.90 (d,
J = 3.6 Hz, 1H), 6.78 (d, J = 3.6 Hz, 1H), 5.92 (s, 1H); 13C
NMR (CDCl3, 100 MHz): δ 159.3, 149.0, 148.1, 137.4, 129.5,
125.5, 123.2, 121.3, 112.8, 71.1. HRMS-ESI (m/z): Calculated
for C10H9NOS (M+H); 269.9588 Found: 254.269.9588.
303 mg, (61%) of 20b as colorless oil; IR (KBr cm-1): 3449,
2996, 2944, 2838, 1606, 1471, 1091, 1031, 917, 816; H NMR
1
(CDCl3, 400 MHz): δ 8.50-8.46 (m, 2H), 7.56 (td, J = 7.6, 1.6
Hz, 2H), 7.27-7.14 (m, 2H), 7.14-7.09 (m, 4H), 7.02-6.99 (m,
2H), 6.76 (d, J = 8.4 Hz, 1H), 6.14 (s, 1H), 4.03-3.98 (m, 2H),
3.93-3.87 (m, 2H), 2.23 (s, 1H), 1.81-1.73 (m, 3H), 1.59-1.48
(m, 3H); 13C NMR (CDCl3, 100 MHz): δ 161.6, 161.5, 154.0,
147.7, 136.7, 131.3, 130.1, 129.1, 128.6, 128.6, 122.2, 121.2,
11.7, 69.7, 69.7, 68.1, 29.1, 22.9, 20.6. HRMS-ESI (m/z):
Benzo[b]thiophen-3-yl(pyridin-2-yl)methanol2 (16b)
179 mg, (74%) of 16b as yellow oil. IR (KBr cm-1): 3139,
2844, 1592, 1430, 1046, 764, 733; 1H NMR (CDCl3, 400
MHz): δ 8.51 (d, J = 4.4 Hz, 1H), 7.48-7.72 (m, 1H), 7.66-7.65
(m, 1H), 7.50 (td, J = 7.6, 1.6 Hz, 1H), 7.21-7.17 (m, 2H),
Calculated for C31H34N2O4 (M+H); 499.2591 Found: 499.2591
.
10 | Org. Biomol. Chem., 2014 00, 1-3
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