MEENAKSHISUNDARAM ET AL.
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1,4‐Bis(3‐benzyl‐6‐methylimidazo[1,2‐a]pyridin‐2‐yl)benzene (20)
White solid. IR (KBr) νmax (cm−1): 3,025, 2,924, 1,609, 1,497, 1,345,
1,047, 802. 1H NMR (CDCl3) δ (ppm): 2.26 (s, 3H), 4.49 (s, 2H), 7.10
(d, J = 7.20 Hz, 1H), 7.14–7.16 (m, 2H), 7.24–7.34 (m, 3H), 7.51 (s,
1H), 7.68 (d, J = 8.20 Hz, 1H), 7.85 (s, 2H). 13C NMR (CDCl3) δ (ppm):
18.35, 29.77, 116.61, 117.80, 121.07, 127.01, 127.74, 127.75,
128.41, 128.42, 129.13, 129.14, 136.67, 145.31, 149.88. HRMS
(ESI): m/z [M+H]+ calcd. for C36H30N4: 519.2468, found: 519.2548.
Anal. calcd. for C36H30N4 (518): C, 83.37, H, 5.83, N, 10.80. Found: C,
83.34, H, 5.89, N, 10.77%.
1,3‐Bis(3‐benzyl‐6‐methylimidazo[1,2‐a]pyridin‐2‐yl)benzene (25)
White solid. IR (KBr) νmax (cm−1): 3,027, 2,920, 1,596, 1,498, 1,339,
1,041, 855. 1H NMR (CDCl3) δ (ppm): 2.32 (s, 3H), 4.43 (s, 2H),
7.05–7.08 (m, 2H), 7.14 (d, J = 7.40 Hz, 1H), 7.19–7.25 (m, 3H), 7.53
(t, J = 8.00 Hz, 1H), 7.58 (s, 1H), 7.61–7.65 (m, 2H), 8.17 (s, 1H). 13C
NMR (101 MHz, CDCl3) δ 143.81, 143.63, 136.85, 134.88, 128.96,
128.84, 127.71, 127.64, 127.53, 127.23, 126.67, 121.67, 120.94,
117.49, 116.75, 77.33, 29.67, 18.32. Anal. calcd. for C36H30N4 (518):
C, 83.37, H, 5.83, N, 10.80. Found: C, 83.34, H, 5.86, N, 10.80%.
1,3‐Bis(3‐benzyl‐7‐methylimidazo[1,2‐a]pyridin‐2‐yl)benzene (26)
White solid. IR (KBr) νmax (cm−1): 3,026, 2,924, 1,595, 1,495, 1,333,
1,040, 852. 1H NMR (DMSO‐d6) δ (ppm): 2.35 (s, 3H), 4.45 (s, 2H),
6.59 (d, J = 7.40 Hz, 1H), 7.08–7.10 (m, 2H), 7.20–7.29 (m, 3H), 7.41
(t, J = 7.80 Hz, 1H), 7.57 (s, 1H), 7.63 (d, J = 6.80 Hz, 1H), 7.67 (d,
J = 7.80 Hz, 1H), 8.03 (s, 1H). 13C NMR (DMSO‐d6) δ (ppm): 13C NMR
(151 MHz, DMSO) δ 160.00, 147.18, 144.44, 141.98, 137.58, 135.23,
135.06, 128.98, 128.89, 127.71, 126.97, 126.68, 126.68, 126.44,
123.65, 118.01, 115.25, 114.78, 20.86. Anal. calcd. for C36H30N4
(518): C, 83.37, H, 5.83, N, 10.80. Found: C, 83.33, H, 5.91, N, 10.76%.
1,4‐Bis(3‐benzyl‐7‐methylimidazo[1,2‐a]pyridin‐2‐yl)benzene (21)
White solid. IR (KBr) νmax (cm−1): 3,022, 2,927, 1,615, 1,498, 1,342,
1,044, 807. 1H NMR (DMSO‐d6) δ (ppm): 2.41 (s, 3H), 4.50 (s, 2H),
6.60 (d, J = 7.20 Hz, 1H), 7.14–7.16 (m, 2H), 7.25–7.32 (m, 3H), 7.53
(s, 1H), 7.61 (d, J = 8.00 Hz, 1H), 7.87 (s, 2H). 13C NMR (DMSO‐d6) δ
(ppm): 13C NMR (151 MHz, DMSO) δ 192.84, 141.73, 140.82, 140.58,
137.77, 137.49, 135.82, 134.98, 133.87, 132.61, 130.10, 128.99,
126.83, 123.89, 119.78, 118.11, 115.29, 114.83, 28.93, 20.93, 15.36.
Anal. calcd. for C36H30N4 (518): C, 83.37, H, 5.83, N, 10.80. Found: C,
83.35, H, 5.87, N, 10.78%.
1,3‐Bis(3‐benzyl‐6‐chloroimidazo[1,2‐a]pyridin‐2‐yl)benzene (27)
White solid. IR (KBr) νmax (cm−1): 3,027, 2,931, 1,594, 1,492, 1,335,
1,042, 851. 1H NMR (DMSO‐d6) δ (ppm): 4.40 (s, 2H), 7.07–7.09 (m,
2H), 7.17 (d, J = 7.80 Hz, 1H), 7.24–7.32 (m, 3H), 7.55 (t, J = 7.40 Hz,
1H), 7.67 (d, J = 7.80 Hz, 1H), 7.72 (s, 1H), 7.84 (d, J = 7.8 Hz, 1H), 8.17
(s, 1H). 13C NMR (151 MHz, DMSO‐d6) δ 144.08, 142.33, 137.44,
135.14, 128.94, 127.75, 126.75, 124.65, 124.43, 118.68, 117.04,
112.35, 40.11, 39.97, 39.84, 39.70, 39.56, 39.42, 39.28, 28.85. HRMS
(ESI): m/z [M+H]+ calcd for C34H24Cl2N4: 559.1375, found: 559.1451.
Anal. calcd. for C34H24Cl2N4 (559): C, 72.99, H, 4.32, N, 10.01. Found:
C, 72.86, H, 4.35, N, 10.06%.
1,4‐Bis(3‐benzyl‐6‐chloroimidazo[1,2‐a]pyridin‐2‐yl)benzene (22)
White solid. IR (KBr) νmax (cm−1): 3,025, 2,922, 1,617, 1,494, 1,339,
1,042, 801. 1H NMR (CDCl3) δ (ppm): 4.51 (s, 4H), 7.13–7.15 (m, 4H),
7.28–7.33 (m, 3H), 7.41–7.44 (m, 5H), 7.61 (d, J = 8.0 Hz, 2H), 7.74 (d,
J = 8.4 Hz, 2H), 8.01 (s, 2H). 13C NMR (CDCl3) δ (ppm): 29.83, 114.13,
119.21, 122.27, 123.50, 124.75, 126.64, 127.12, 127.98, 128.54,
129.15, 130.37, 136.57. Anal. calcd. for C34H24Cl2N4 (559): C, 72.99,
H, 4.32, N, 10.01. Found: C, 72.95, H, 4.30, N, 10.08%.
1,4‐Bis(3‐(4‐methylbenzyl)imidazo[1,2‐a]pyridin‐2‐yl)benzene (23)
White solid. IR (KBr) νmax (cm−1): 3,020, 2,919, 1,615, 1,484, 1,340,
1,045, 803. 1H NMR (CDCl3) δ (ppm): 2.33 (s, 3H), 4.49 (s, 2H), 6.86
(t, J = 7.40 Hz, 1H), 7.02 (d, J = 7.80 Hz, 2H), 7.13 (d, J = 8.00 Hz, 2H),
7.28–7.35 (m, 2H), 7.79 (d, J = 7.20 Hz, 1H), 7.90 (s, 2H). 13C NMR
(CDCl3) δ (ppm): 21.10, 29.44, 112.69, 117.44, 123.84, 124.93,
127.93, 128.07, 128.35, 129.29, 129.87, 129.95, 133.48, 136.65,
144.59. Anal. calcd. for C36H30N4 (518): C, 83.37, H, 5.83, N, 10.80.
Found: C, 83.35. H, 5.87, N, 10.78%.
1,3‐Bis(3‐(4‐methylbenzyl)imidazo[1,2‐a]pyridin‐2‐yl)benzene (28)
White solid. IR (KBr) νmax (cm−1): 3,024, 2,932, 1,590, 1,491, 1,337,
1,045, 853. 1H NMR (DMSO‐d6) δ (ppm): 2.32 (s, 3H), 4.49 (s, 2H),
6.90 (t, J = 7.20 Hz, 1H), 6.99 (d, J = 7.80 Hz, 2H), 7.08 (d, J = 8.00 Hz,
2H), 7.37–7.43 (m, 2H), 7.63 (t, J = 7.80 Hz, 1H), 7.79 (d, J = 7.20 Hz,
1H), 7.94 (d, J = 7.20 Hz, 1H), 8.25 (s, 1H). 13C NMR (DMSO‐d6) δ
(ppm): 21.35, 29.66, 112.70, 117.51, 118.42, 123.85, 127.14, 128.01,
128.21, 128.22, 129.15, 129.35, 132.03, 135.13, 136.22, 144.05,
145.11. Anal. calcd. for C36H30N4 (518): C, 83.37, H, 5.83, N, 10.80.
Found: C, 83.32, H, 5.85, N, 10.83%.
1,3‐Bis(3‐benzylimidazo[1,2‐a]pyridin‐2‐yl)benzene (24)
White solid. IR (KBr) νmax (cm−1): 3,028, 2,919, 1,599, 1,494, 1,343,
1,036, 852. 1H NMR (CDCl3) δ (ppm): 4.42 (s, 2H), 6.68 (t, J = 8.20 Hz,
1H), 7.07–7.09 (m, 2H), 7.16 (d, J = 7.80 Hz, 1H), 7.20–7.28 (m, 3H),
7.55 (t, J = 8.00 Hz, 1H), 7.65–7.67 (m, 2H), 7.85 (d, J = 7.80 Hz, 1H),
8.18 (s, 1H). 13C NMR (CDCl3) δ (ppm): 29.88, 112.33, 117.72,
118.09, 123.81, 124.36, 127.02, 127.99, 128.18, 128.19, 129.15,
129.39, 134.99, 136.89, 144.10, 144.96. Anal. calcd. for C34H26N4
(490): C, 83.24, H, 5.34, N, 11.42. Found: C, 83.25, H, 5.37, N, 11.38%.
3‐Benzyl‐7‐methyl‐2‐phenylimidazo[1,2‐a]pyridine (29)
White solid. 1H NMR (CDCl3) δ (ppm): 2.26 (s, 3H), 4.48 (s, 2H), 7.11
(dd, J = 1.80, 8.40 Hz, 1H), 7.16 (d, J = 7.4 Hz, 2H), 7.27–7.38 (m, 4H),
7.43–7.45 (m, 2H), 7.51 (s, 1H), 7.69 (d, J = 8.80 Hz, 1H), 7.79 (dd,
J = 2.0, 7.40 Hz, 2H). Anal. calcd. for C21H18N2 (298.38): C, 84.53, H,
6.08, N, 9.39. Found: C, 84.52, H, 6.10, N, 9.38%.