7
2.54 (q, J = 7.5 Hz, 2H), 1.13 (t, J = 7.6 H
A
z,
C
3H
C
);E1P3C
T
N
E
M
D
R
MA12
N
7.
U
66
S
,
C
1
R
27
I
.34 , 126.51 , 124.47 , 112.42 (d, J = 5.4 Hz),
P
T
(CDCl3, 101 MHz) δ: 154.23 , 139.43 , 138.95 , 132.66 , 130.82
, 130.09 , 129.40 , 128.60 , 127.62 , 127.50 , 126.35 , 122.09 ,
119.16 , 117.15 , 114.79 , 28.01 , 18.32 , 15.61; HRMS:
calculated for C22H20N2O [M+H]+: 329.1655, found: 329.1648.
95.53 (d, J = 16.5 Hz), 16.90; HRMS: calculated for C21H17FN2O
[M+H]+ : 333.1403, found:333.1398.
6-methyl-2-phenyl-3-(m-tolyloxy)imidazo[1,2-a]pyridine (3II-
11). yellow solid (145 mg, 92 % yield), mp: 124-126 °C, H
1
methyl 3-(4-ethylphenoxy)-2-phenylimidazo[1,2-a]pyridine-5-
carboxylate (3II-6). green oil (88 mg, 47 % yield), H NMR
NMR (CDCl3, 400 MHz) δ: 7.98-7.91 (m, 2H), 7.49-7.39 (m,
2H), 7.29 (dd, J = 8.4, 7.0 Hz, 2H), 7.17 (tt, J = 6.7, 1.3 Hz, 1H),
7.09 (t, J = 7.9 Hz, 1H), 6.94 (dd, J = 9.2, 1.7 Hz, 1H), 6.86-6.79
(m, 1H), 6.72-6.61 (m, 2H), 2.21 (s, 3H), 2.17 (d, J = 1.1 Hz,
3H); 13C NMR (CDCl3, 101 MHz) δ: 156.21 , 140.52 , 139.01 ,
132.68 , 130.88 , 129.86 , 129.83 , 128.61 , 127.63 , 127.51 ,
126.33 , 124.44 , 122.10 , 119.12 , 117.16 , 115.54 , 111.92 ,
1
(CDCl3, 400 MHz) δ: 8.01 – 7.93 (m, 2H), 7.76 (dd, J = 8.9, 1.3
Hz, 1H), 7.29 (d, J = 7.3 Hz, 2H), 7.22 – 7.16 (m, 1H), 7.13 (dd,
J = 8.9, 7.0 Hz, 1H), 7.06 (dd, J = 7.0, 1.3 Hz, 1H), 7.00 – 6.93
(m, 2H), 6.64 – 6.57 (m, 2H), 3.57 (s, 3H), 2.47 (q, J = 7.6 Hz,
2H), 1.07 (t, J = 7.6 Hz, 3H); 13C NMR (CDCl3, 101 MHz) δ:
162.00 , 153.79 , 139.98 , 139.43 , 131.88 , 131.48 , 129.19 ,
128.84 , 128.63 , 128.16 , 127.78 , 126.90 , 123.23 , 120.70 ,
116.30 , 114.66 , 52.96 , 27.97 , 15.62; HRMS: calculated for
C23H20N2O3 [M+H]+ : 373.1554, found: 373.1547.
21.49 , 18.31; HRMS: calculated for C21H18N2O [M+H]+
315.1501, found: 315.1492.
:
3-(3-methoxyphenoxy)-6-methyl-2-phenylimidazo[1,2-a]
pyridine (3II-12). white solid (129 mg, 78 % yield), mp: 163-
1
5-fluoro-2-phenyl-3-(m-tolyloxy)imidazo[1,2-a]pyridine (3II-7).
brown oil (131 mg, 82 % yield); H NMR (CDCl3, 400 MHz) δ:
165 °C, H NMR (CDCl3, 400 MHz) δ: 8.01 (dd, J = 8.3, 1.3 Hz,
1
2H), 7.55-7.47 (m, 2H), 7.37 (dd, J = 8.4, 7.0 Hz, 2H), 7.25 (t, J
= 7.4 Hz, 1H), 7.18 (t, J = 8.2 Hz, 1H), 7.01 (dd, J = 9.2, 1.8 Hz,
1H), 6.64 (dd, J = 8.0, 2.4 Hz, 1H), 6.55 (t, J = 2.4 Hz, 1H), 6.51-
6.46 (m, 1H), 3.74 (s, 3H), 2.25 (d, J = 1.1 Hz, 3H); 13C NMR
(CDCl3, 101 MHz) δ: 161.27 , 157.37 , 139.01 , 132.61 , 130.94
, 130.66 , 129.68 , 128.63 , 127.69 , 127.57 , 126.37 , 122.18 ,
119.10 , 117.18 , 109.00 , 107.03 , 101.60 , 55.44 , 18.32;
HRMS: calculated for C21H18N2O2 [M+H]+ : 331.1445, found:
331.1441.
8.04 (dd, J = 8.4, 1.3 Hz, 2H), 7.46-7.34 (m, 3H), 7.34-7.23 (m,
2H), 7.21-7.09 (m, 2H), 6.90 (d, J = 7.5 Hz, 1H), 6.77 (t, J = 1.9
Hz, 1H), 6.72 (dd, J = 8.3, 2.6 Hz, 1H), 6.36-6.28 (m, 1H), 2.29
(s, 3H); 13C NMR (CDCl3, 101 MHz) δ: 157.69 , 150.38 , 147.69
, 142.13 , 140.31 , 132.13 , 131.89 , 129.67 , 128.70 , 128.07 ,
126.69 , 125.32 , 124.33 , 115.75 , 113.59 (d, J = 5.3 Hz),
112.09 , 93.38 (d, J = 16.3 Hz), 21.49; HRMS: calculated
forC20H15FN2O[M+H]+ : 319.1247, found: 319.1241.
5-fluoro-3-(3-methoxyphenoxy)-2-phenylimidazo[1,2-a]
pyridine (3II-8). yellow oil (134 mg, 80 % yield); 1H NMR
(CDCl3, 400 MHz) δ: 7.96 (dd, J = 8.4, 1.3 Hz, 2H), 7.75 (dd, J =
9.9, 4.8 Hz, 1H), 7.69-7.62 (m, 1H), 7.38-7.29 (m, 2H), 7.29-
7.22 (m, 1H), 7.22-7.09 (m, 2H), 6.61 (ddd, J = 8.4, 2.4, 0.8 Hz,
1H), 6.48 (t, J = 2.4 Hz, 1H), 6.41 (ddd, J = 8.3, 2.5, 0.8 Hz, 1H),
3.69 (s, 3H); 13C NMR (CDCl3, 101 MHz) δ: 161.42 , 156.50 ,
152.56 , 136.50 , 131.23 , 130.93 , 130.36 , 128.93 , 128.65 ,
126.60 , 118.28 , 118.03 , 117.89 , 117.80 , 109.63 , 108.95 ,
108.53 , 106.80 , 101.65 , 55.51; HRMS: calculated for
C20H15FN2O2[M+H]+:335.1191, found:335.1190.
3-(4-ethylphenoxy)-6-methyl-2-phenylimidazo[1,2-
a]pyridine(3II-13).white solid (146 mg, 89 % yield), mp: 98-99
1
°C, H NMR (CDCl3, 400 MHz) δ: 8.06-7.99 (m, 2H), 7.56-7.48
(m, 2H), 7.36 (t, J = 7.7 Hz, 2H), 7.29-7.21 (m, 1H), 7.11 (d, J =
8.6 Hz, 2H), 7.01 (dd, J = 9.1, 1.8 Hz, 1H), 6.92-6.82 (m, 2H),
2.60 (q, J = 7.6 Hz, 2H), 2.25 (d, J = 1.1 Hz, 3H), 1.20 (t, J = 7.6
Hz, 3H).13C NMR (CDCl3, 101 MHz) δ: 154.23 , 139.43 , 138.95
, 132.66 , 130.82 , 130.09 , 129.40 , 128.60 , 127.62 , 127.50 ,
126.35 , 122.09 , 119.16 , 117.15 , 114.79 , 28.01 , 18.32 ,
15.61 .HRMS: calculated for C22H20N2O[M+H]+ :329.1655,
found:329.1648.
5-fluoro-3-(4-nitrophenoxy)-2-phenylimidazo[1,2-a] pyridine
(3II-9). yellow solid (159 mg, 91 % yield), mp: 144-146 °C, H
6-methyl-3-(4-nitrophenoxy)-2-phenylimidazo[1,2-
1
a]pyridine(3II-14).yellow solid (155 mg, 90 % yield), mp: 145-
147 °C,1H NMR (CDCl3, 400 MHz) δ: 8.19-8.10 (m, 2H), 7.92-
7.84 (m, 2H), 7.65 (d, J = 9.2 Hz, 1H), 7.45 (s, 1H), 7.31 (t, J =
7.5 Hz, 2H), 7.27-7.17 (m, 1H), 7.11 (dd, J = 9.3, 1.7 Hz, 1H),
7.05-6.96 (m, 2H), 2.24 (d, J = 1.1 Hz, 3H).13C NMR (CDCl3,
101 MHz) δ: 160.92 , 144.13 , 143.00 , 132.29 , 132.03 ,
131.30 , 130.01 , 128.90 , 127.89 , 126.65 , 126.12 , 125.61 ,
125.52 , 124.41 , 115.84 , 115.68 , 113.02 .HRMS: calculated
for C20H15N3O3 [M+H]+ : 346.1194, found: 346.1186.
NMR (CDCl3, 400 MHz) δ: 8.17-8.08 (m, 2H), 7.92-7.84 (m,
2H), 7.39 (d, J = 9.1 Hz, 1H), 7.30 (dd, J = 8.3, 6.7 Hz, 2H),
7.27-7.19 (m, 1H), 7.13 (ddd, J = 9.1, 7.5, 6.1 Hz, 1H), 7.03-
6.94 (m, 2H), 6.36-6.28 (m, 1H); 13C NMR (CDCl3, 101 MHz) δ:
161.97 , 150.04 , 147.36 , 143.85 , 142.27 (d, J = 3.9 Hz),
132.44 , 131.09 , 128.89 , 128.64 , 128.15 (d, J = 1.8 Hz),
126.67 , 126.33 , 126.10 (d, J = 6.0 Hz), 115.77 , 113.78 (d, J =
5.1 Hz), 94.00 (d, J = 16.2 Hz); HRMS: calculated for
C19H12FN3O3 [M+H]+ : 350.0941, found: 350.0935.
3-(2,6-dimethylphenoxy)-6-methyl-2-phenylimidazo[1,2-
3-(2,6-dimethylphenoxy)-5-fluoro-2-phenylimidazo[1,2-a]
pyridine(3II-10). yellow oil (123 mg, 74 % yield); 1H NMR
(CDCl3, 400 MHz) δ: 7.76 – 7.66 (m, 3H), 7.31 – 7.17 (m, 4H),
6.92 – 6.81 (m, 3H), 6.48 (t, J = 6.8 Hz, 1H), 1.99 (s, 6H); 13C
NMR (CDCl3, 101 MHz) δ: 153.29 , 150.26 , 147.55 , 139.25 ,
132.97 (d, J = 3.4 Hz), 130.11 , 129.13 , 128.78 , 128.58 ,
a]pyridine(3II-15).yellow solid (130 mg, 79 % yield), mp: 143-
145 °C, H NMR (CDCl3, 400 MHz) δ: 7.81-7.74 (m, 2H,ArH),
7.58 (d, J = 9.2 Hz, 1H,ArH), 7.39-7.34 (m, 1H,ArH), 7.29-7.21
(m, 2H,ArH), 7.21-7.12 (m, 1H,ArH), 6.98 (dd, J = 9.2, 1.6 Hz,
1H,ArH), 6.94-6.86 (m, 3H,ArH), 2.18 (d, J = 1.1 Hz, 3H,CH3),
2.00 (s, 6H,CH3,CH3); 13C NMR (CDCl3, 101 MHz) δ: 151.91 ,
1