MUTKULE ET AL.
5
7-methyl-3-nitro-2-p-tolyl-imidazo[1,2-a]pyridine (3aa)
8-methyl-3-nitro-2-phenyl-imidazo [1,2-a]pyridine (3bd)
1
1
Yellow solid (1.56 g, 95%), mp 169ꢀC-171ꢀC; H NMR
Yellow solid (1.33 g, 78%), mp 167ꢀC-169ꢀC; H NMR
(DMSO, 400 MHz): δ 9.25 (d, J = 9.5 Hz, 1H), 7.72 (d,
J = 10.8 Hz, 3H), 7.28 (d, J = 6.5 Hz, 3H), 2.45 (s, 3H),
2.36 (s, 3H); 13C NMR (DMSO, 100 MHz): δ 150.1, 145.5,
143.9, 140.1, 130.3, 129.8, 129.3, 128.9, 128.4, 128.1, 119.5,
116.8, 21.5, 21.3. MS (ES+): m/z = 268.1 [M + H] +.
3-nitro-2-p-tolylimidazo[1,2-a]pyridine (3ab)
(400 MHz, CDCl3): δ 9.38 (d, J = 7.2 Hz, 1H), 7.92-7.90
(m, 2H), 7.52-7.49 (m, 3H), 7.46 (d, J = 7.2 Hz, 1H), 7.18
(t, J = 7.2 Hz, 1H), 2.73 (s, 3H); 13C NMR (CDCl3,
100 MHz): δ149.7, 145.1, 132.2, 130.1, 130, 129.9, 128.6,
128.1, 125.9, 116.4. 16.6. MS (ES+): m/z = 253.9
[M + H]+.
1
Yellow solid (1.22 g, 78%), mp 195ꢀC-197ꢀC; H NMR
2-(4-methoxyphenyl)-7-methyl-3-nitro-imidazo[1,2-a]
pyridine (3ca)
(DMSO, 400 MHz) δ 9.39 (d, J = 9.3 Hz, 1H), 7.93 (d,
J = 11.2 Hz, 1H), 7.80 (t, J = 12 Hz, 1H), 7.73 (d, J = 10.8 Hz,
2H), 7.44 (t, J = 12 Hz, 1H), 7.30 (d, J = 10.5 Hz, 2H), 2.37
(s, 3H); 13C NMR (DMSO, 100 MHz): δ 149.7, 145.1, 140.1,
132.3, 130.3, 129.7, 128.9, 118.1, 117.4, 21.5.
1
Yellow solid (1 g, 65%), mp 165ꢀC-167ꢀC; H NMR
(DMSO, 400 MHz): δ 9.26 (d, J = 9.5 Hz, 1H), 7.83 (d,
J = 11.7 Hz, 2H), 7.70 (s, 1H), 7.27 (d, J = 8.6 Hz, 1H),
7.03 (d, J = 11.7 Hz, 2H), 3.82 (s, 3H), 2.47 (s, 3H); 13C
NMR (CDCl3, 100 MHz): δ 161.1, 149.9, 145.6, 144, 132.1,
128.1, 124.7, 119.4, 116.7, 113.7, 55.7, 21.3. MS (ES+): m/
z = 283.9 [M + H]+.
MS (ES+): m/z = 253.9 [M + H]+.
6-bromo-3-nitro-2-p-tolyl-imidazo[1,2-a]pyridine (3ac)
1
Yellow solid (1.62 g, 81%), mp 172ꢀC-174ꢀC; H NMR
(DMSO, 400 MHz): δ 9.44 (s, 1H), 7.96 (d, J = 12.5 Hz,
1H), 7.90 (d, J = 12.5 Hz, 1H), 7.72 (d, J = 10.8 Hz, 2H),
7.30 (d, J = 10.6 Hz, 2H), 2.37 (s, 3H); 13CNMR (DMSO,
100 MHz): δ 149.5, 143.6, 140.3, 134.9, 130.2, 129.3,
129, 128.5, 119.2, 111, 21.5.
2-(4-methoxyphenyl)-3-nitro-imidazo[1,2-a]pyridine (3cb)
1
Yellow solid (1.37 g, 91%), mp 179ꢀC-181ꢀC; H NMR
(DMSO, 400 MHz): δ 9.39 (d, J = 8.6 Hz, 1H), 7.92-7.76
(m, 4H), 7.42 (t, J = 9.3 Hz, 1H), 7.04 (d, J = 12.6 Hz,
2H), 3.82 (s, 3H); 13C NMR (CDCl3, 100 MHz): δ 149.6,
145.2, 132.4, 132.1, 128.9, 124.6, 118, 117.3, 113.8, 55.7.
MS (ES+): m/z = 269.9 [M + H]+.
MS (ES+): m/z = 333.8 [M + H]+.
8-methyl-3-nitro-2-p-tolyl-imidazo[1,2-a]pyridine (3ad)
1
Yellow solid (1.15 g, 70%), mp 126ꢀC-128ꢀC; H NMR
6-bromo-2-(4-methoxyphenyl)-3-nitro-imidazo[1,2-a]
pyridine (3cc)
(CDCl3, 400 MHz): δ 9.37 (d, J = 6.8 Hz, 1H), 7.83 (d,
J = 8.4 Hz, 2H), 7.44 (d, J = 7.2 Hz, 1H), 7.32 (d,
J = 8 Hz, 2H), 7.16 (t, J = 7.2 Hz, 1H), 2.72 (s, 3H), 2.44
(s, 3H); 13C NMR (CDCl3, 100 MHz):δ 149.9, 145.2, 140.3,
130, 129.9, 129.2, 128.8, 128.4, 125.9, 116.3, 21.5, 16.6. MS
(ES+): m/z = 268.8 [M + H]+.
1
Yellow solid (1.17 g, 60%), mp 162ꢀC-164ꢀC; H NMR
(DMSO, 400 MHz): δ 9.43 (s, 1H), 7.96-7.80 (m, 4H), 7.03
(d, J = 11.8 Hz, 2H), 3.82 (s, 3H); 13C NMR (CDCl3,
100 MHz): δ 161.2, 149.3, 143.6, 134.9, 132.1, 129.1, 128.5,
124.2, 119, 113.9, 110.8, 55.7. MS (ES+): m/z = 349.8
[M + H]+.
7-methyl-3-nitro-2-phenyl-imidazo[1,2-a]pyridine (3ba)
1
Yellow solid (1.45 g, 85%), mp 169ꢀC-171ꢀC; H NMR
2-(4-methoxyphenyl)-8-methyl-3-nitro-imidazo[1,2-a]
pyridine (3cd)
(DMSO, 400 MHz): δ 9.25 (d, J = 9.5 Hz, 1H), 7.82-7.79
(m, 2H), 7.72 (s, 1H), 7.50-7.46 (m, 3H), 7.29 (d,
J = 9.5 Hz, 1H), 2.46 (s, 3H); 13CNMR (DMSO, 100 MHz):
δ 149.9, 145.5, 144, 132.7, 130.3, 130.2, 129, 128.3,
128, 119.7, 116.9, 21.3.
1
Yellow solid (1 g, 63%), mp 161ꢀC-163ꢀC; H NMR
(CDCl3, 400 MHz): δ 9.38 (d, J = 6.8 Hz, 1H), 7.95 (d,
J = 6.8 Hz, 2H), 7.44 (d, J = 7.2 Hz, 1H), 7.15 (t,
J = 6.8 Hz, 1H), 7.03 (d, J = 6.8 Hz, 2H), 3.89 (s, 3H), 2.72
(s, 3H); 13C NMR (CDCl3, 100 MHz): δ 161.1, 149.7,
145.2, 131.8, 129.9, 128.3, 126.1, 124.4, 116.2, 113.6, 55.4,
16.6. MS (ES+): m/z = 283.9 [M + H]+.
MS (ES+): m/z = 253.9 [M + H]+.
3-nitro-2-phenyl-imidazo[1,2-a]pyridine (3bb)
1
Yellow solid (1.5 g, 93%), mp 167ꢀC-169ꢀC; H NMR
(400 MHz, DMSO): δ 9.40 (d, J = 9.3 Hz, 1H), 7.94 (d,
J = 11.4 Hz, 1H), 7.84-7.78 (m, 3H), 7.52-7.43 (m, 4H),
13CNMR (DMSO, 100 MHz): δ 149.6, 145.1, 132.7, 132.3,
130.3, 130.2, 128.9, 128.3, 118.2, 117.5.
2-(3-chlorophenyl)-7-methyl-3-nitro-imidazo[1,2-a]pyr-
idine (3da)
1
Yellow solid (1.41 g, 90%), mp 179ꢀC-181ꢀC; H NMR
(CDCl3, 400 MHz) δ 9.37 (d, J = 7.2 Hz, 1H), 7.89 (s, 1H),
7.79 (d, J = 7.2 Hz, 1H), 7.60 (s, 1H), 7.47-7.41 (m, 2H),
7.13 (d, J = 7.2 Hz, 1H), 2.56 (s, 3H); 13C NMR (CDCl3,
100 MHz): δ 148.9, 145.5, 143.3, 134.1, 133.7, 130.1,
130, 129.3128.2, 127.3, 119.2, 117.1, 21.6. MS (ES+): m/
z = 288.8 [M + H]+.
MS (ES+): m/z = 239.8 [M + H]+.
6-bromo-3-nitro-2-phenyl-imidazo[1,2-a]pyridine (3bc)
1
Yellow solid (1.90 g, 89%), mp 166ꢀC-168ꢀC; H NMR
(DMSO, 400 MHz): δ 9.43 (s, 1H), 7.97-7.89 (m, 2H),
7.81-7.78 (m, 2H), 7.50-7.45 (m, 3H); 13C NMR (DMSO,
100 MHz): δ 150.1, 145.5, 143.9, 140, 130.3, 129.8, 129.3,
128.9, 128.4, 128, 119.5, 116.8, 21.4. MS (ES+): m/z =
319.8 [M + H]+.
2-(3-chlorophenyl)-3-nitro-imidazo[1,2-a]pyridine (3db)
1
Yellow solid (1.41 g, 94%), mp 166ꢀC-168ꢀC; H NMR
(CDCl3, 400 MHz) δ 9.51 (d, J = 6.8 Hz, 1H), 7.90 (s, 1H),