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209–211 °C. H NMR (500 MHz, CDCl3) δ = 0.81 (t, J = 7.4 Hz, 3H),
9,12-Dimethoxy-7-(p-tolyl)benzo[4,5]imidazo[1,2-a]benzo[4,5]-
imidazo[1,2-c]pyrimidine (3q). Rf = 0.51. White solid (72 mg,
63 %); m.p. 269–273 °C. H NMR (500 MHz, CDCl3) δ = 2.44 (s, 3H),
1.29–1.37 (m, 2H) 1.70–1.76 (m, 2H), 2.78 (t, J = 8.0 Hz, 2H), 5.84 (d,
J = 8.4 Hz, 1H), 6.90–6.93 (m, 1H), 7.30–7.33 (m, 1H), 7.54–7.59 (m,
4H), 7.66–7.74 (m, 3H), 7.86 (d, J = 7.8 Hz, 1H), 8.00–8.03 (m, 1H),
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3.96 (s, 3H), 3.98 (s, 3H), 6.67 (d, J = 8.5 Hz, 1H), 6.76 (d, J = 8.5 Hz,
8.85–8.89 (m, 1H); 13C NMR (125 MHz, CDCl3) δ = 13.8, 22.7, 26.9, 1H), 7.14–7.18 (m, 1H), 7.31–7.34 (m, 1H), 7.40 (d, J = 7.7 Hz, 1H),
31.8, 112.9, 114.3, 115.0, 119.4, 119.7, 121.8, 123.9, 124.2, 125.4,
129.2 (129.18), 129.2 (129.23), 1295, 129.8, 130.5, 131.7, 137.4, 142.4,
144.3, 146.6. HRMS (EI) calcd. for C26H22N4 (M+) 390.1844, found
390.1846.
7.63 (s, 1H), 7.72 (d, J = 7.7 Hz, 1H), 7.76 (d, J = 8.4 Hz, 1H), 8.65–
8.68 (m, 1H); 13C NMR (125 MHz, CDCl3) δ = 14.3, 56.4, 57.2, 112.8,
115.4, 116.0, 119.9, 120.4, 121.2, 123.3, 124.5, 124.8, 125.8, 128.7,
130.4, 130.8, 141.8, 142.8, 144.1, 145.0, 156.1, 157.3. HRMS (EI) calcd.
for C23H18N4O2 (M+) 382.1430, found 382.1433.
6,7-Diphenylbenzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]-
pyrimidine (3l). Rf = 0.47. White solid (95 mg, 77 %); m.p. 278–
12,15-Dimethoxybenzo[f]benzo[4,5]imidazo[1,2-a]benzo[4,5]-
imidazo[1,2-c]quinazoline (3r). Rf = 0.51. White solid (104 mg,
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280 °C. H NMR (500 MHz, CDCl3) δ = 5.85 (d, J = 8.4 Hz, 1H), 6.91–
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83 %); m.p. 287–290 °C. H NMR (500 MHz, CDCl3) δ = 3.55 (s, 3H),
6.94 (m, 1H), 7.11–7.15 (m, 1H), 7.24–7.28 (m, 4H), 7.31–7.37 (m, 4H),
7.51–7.53 (m, 2H), 7.56–7.60 (m, 2H), 7.87 (d, J = 7.7 Hz, 1H), 8.01–
8.04 (m, 1H), 8.86–8.90 (m, 1H); 13C NMR (125 MHz, CDCl3) δ = 102.2,
106.3, 109.3, 112.7, 114.8, 119.2, 119.4, 121.7, 123.8, 124.0, 125.3,
127.8, 128.7, 129.4, 129.5, 129.8, 129.9, 130.2, 130.4, 131.6, 137.4,
142.1, 144.0, 146.9. HRMS (EI) calcd. for C28H18N4 (M+) 410.1531,
found 410.1534.
4.09 (s, 3H), 6.76 (d, J = 8.6 Hz, 1H), 7.07 (d, J = 8.6 Hz, 1H), 7.52–
7.57 (m, 2H), 7.75–7.78 (m, 1H), 7.91 (d, J = 7.4 Hz, 1H), 8.00–8.01
(m, 1H), 8.07 (d, J = 9.1 Hz, 1H), 8.16 (d, J = 8.2 Hz, 1H), 8.42 (d, J =
9.1 Hz, 1H), 8.84–8.87 (m, 1H), 10.53 (d, J = 8.7 Hz, 1H); 13C NMR
(125 MHz, CDCl3) δ = 55.3, 56.1, 112.2, 112.6, 114.0, 117.2, 118.7,
119.0, 121.6, 123.3, 123.4, 124.2, 125.4, 126.6, 127.1, 128.2, 129.1,
129.3, 132.2, 132.7, 140.8, 141.9, 142.9, 143.6, 146.9, 148.5. HRMS
(EI) calcd. for C26H18N4O2 (M+) 418.1430, found 418.1427.
Benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]quinazoline-
13-carbonitrile (3m). Rf = 0.31. White solid (50 mg, 50 %); m.p.
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11,14-Dimethoxy-2,3-dimethylbenzo[4,5]imidazo[1,2-a]benzo-
[4,5]imidazo[1,2-c]quinazoline (3s). Rf = 0.51. White solid (92 mg,
314–316 °C. H NMR (500 MHz, CDCl3) δ = 7.57–7.61 (m, 2H), 7.64–
7.67 (m, 1H), 7.73 (dd, J = 8.6 and 1.6 Hz, 1H), 7.84–7.88 (m, 1H),
7.98–8.01 (m, 1H), 8.23 (d, J = 1.3 Hz, 1H), 8.26 (d, J = 8.6 Hz, 1H),
8.34 (d, J = 8.4 Hz, 1H) 8.73–8.77 (m, 1H), 8.80 (dd, J = 7.9 and
1.4 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ = 107.9, 113.6, 115.0, 115.1,
115.2, 119.1, 120.0, 124.4, 125.0, 125.9, 126.5, 126.6, 127.1, 130.3,
132.4, 133.0, 133.5, 142.7, 143.5, 143.9, 144.3. HRMS (EI) calcd. for
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77 %); m.p. 232–234 °C. H NMR (500 MHz, CDCl3) δ = 2.44 (s, 3H),
2.48 (s, 3H), 3.88 (s, 3H), 4.10 (s, 3H), 6.60 (d, J = 8.6 Hz, 1H), 6.91
(d, J = 8.6 Hz, 1H), 7.43–7.46 (m, 1H), 7.60 (s, 1H), 7.65–7.69 (m, 1H),
8.16 (d, J = 8.4 Hz, 1H), 8.34 (s, 1H), 8.59 (dd, J = 7.9 and 1.5 Hz,
1H); 13C NMR (125 MHz, CDCl3) δ = 20.5, 20.6, 55.9, 56.6, 114.6,
114.7, 116.8, 119.5, 119.8, 122.7, 124.0, 125.0, 126.2, 128.6, 130.0,
131.3, 132.6, 133.8, 134.3, 141.6, 142.2, 143.6, 144.7, 148.2. HRMS
(EI) calcd. for C24H20N4O2 (M+) 396.1586, found 396.1583.
C
21H11N5 (M+) 333.1014, found 333.1013.
11,14-Dimethoxybenzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo-
[1,2-c]quinazoline (3n). Rf = 0.51. White solid (85 mg, 77 %); m.p.
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11,14-Dimethoxy-6,7,8,9-tetrahydrobenzo[4,5]imidazo[1,2-a]-
benzo[4,5]imidazo[1,2-c]quinazoline (3t). Rf = 0.53. White solid
(82 mg, 73 %); m.p. 251–253 °C. 1H NMR (500 MHz, CDCl3) δ = 1.99–
2.03 (m, 2H), 2.11–2.16 (m, 2H), 3.06–3.09 (m, 2H), 3.33–3.35 (m, 2H),
3.77 (s, 3H), 3.99 (s, 3H), 6.82 (d, J = 8.5 Hz, 1H), 7.20 (d, J = 8.6 Hz,
1H), 7.39–7.42 (m, 1H), 7.87–7.89 (m, 1H), 7.92–7.97 (m, 1H), 8.72–
8.76 (m, 1H); 13C NMR (125 MHz, CDCl3) δ = 21.2, 22.4, 23.3, 27.4,
55.4, 56.0, 113.6, 115.1, 117.6, 119.6, 119.9, 122.3, 123.8, 124.4, 125.5,
130.0, 132.2, 138.0, 142.6, 144.4, 146.7, 148.2. HRMS (EI) calcd. for
221–223 °C. H NMR (500 MHz, CDCl3) δ = 3.99 (s, 3H), 4.01 (s, 3H),
6.71 (d, J = 8.9 Hz, 1H), 6.81 (d, J = 8.9 Hz, 1H), 7.44–7.47 (m, 1H),
7.58–7.59 (m, 1H), 7.67–7.71 (m, 1H), 7.89–7.93 (m, 1H), 7.99 (d, J =
8.0 Hz, 1H), 8.21 (d, J = 8.4 Hz, 1H), 8.55 (dd, J = 7.9 and 1.5 Hz,
1H), 8.58–8.62 (m, 1H); 13C NMR (125 MHz, CDCl3) δ = 55.3, 56.4,
111.3, 113.1, 113.6, 118.2, 118.7, 121.7, 122.9, 123.0, 123.9, 125.2,
128.7, 129.0, 130.6, 132.7, 140.3, 141.1, 142.4, 142.9, 143.2, 144.8.
HRMS (EI) calcd. for C22H16N4O2 (M+) 368.1273, found 368.1272.
7-Fluoro-11,14-dimethoxybenzo[4,5]imidazo[1,2-a]benzo[4,5]-
imidazo[1,2-c]quinazoline (3o). Rf = 0.55. White solid (81 mg,
C
22H20N4O2 (M+) 372.1586, found 372.1583.
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9,12-Dimethoxy-7-phenylbenzo[4,5]imidazo[1,2-a]benzo[4,5]-
imidazo[1,2-c]pyrimidine (3u). Rf = 0.51. White solid (75 mg,
70 %); m.p. 289–292 °C. H NMR (500 MHz, CDCl3) δ = 3.90 (s, 3H),
4.01 (s, 3H), 6.51 (d, J = 8.6 Hz, 1H), 6.82 (d, J = 8.6 Hz, 1H), 7.39–
7.41 (m, 2H), 7.60 (dd, J = 8.7 and 5.2 Hz, 1H), 7.87–7.89 (m, 1H),
8.00 (d, J = 7.9 Hz, 1H), 8.58 (dd, J = 9.5 and 2.3 Hz, 1H), 8.72–8.74
(m, 1H); 13C NMR (125 MHz, CDCl3) δ = 54.8, 55.6, 110.2 (d, J =
23.7 Hz), 113.2, 114.8, 118.1 (d, J = 23.6 Hz), 120.4, 121.6, 123.9 (d,
J = 9.7 Hz), 126.4, 127.4, 128.1 (d, J = 8.3 Hz), 129.1, 131.6, 132.9,
136.1, 137.4, 138.7, 141.1, 145.0, 147.1 (d, J = 4.3 Hz), 161.3 (d, J =
246.6 Hz). HRMS (EI) calcd. for C22H15N4O2 (M+) 38d6.1179, found
386.1178.
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63 %); m.p. 284–286 °C. H NMR (500 MHz, CDCl3) δ = 3.66 (s, 3H),
3.97 (s, 3H), 6.64 (d, J = 8.9 Hz, 1H), 6.77 (d, J = 8.5 Hz, 1H), 6.88–
6.92 (m, 1H), 7.29–7.32 (m, 1H), 7.47–7.50 (m, 2H), 7.62 (s, 1H), 7.67–
7.74 (m, 3H), 7.84–7.86 (m, 1H), 8.83–8.87 (m, 1H); 13C NMR
(125 MHz, CDCl3) δ = 56.6, 58.4, 113.6, 115.8, 117.3, 120.1, 120.4,
122.6, 124.7, 124.9, 126.2, 130.4, 130.48, 130.50, 131.3, 132.5, 138.3,
143.1, 144.9, 147.9, 153.5, 155.2. HRMS (EI) calcd. for C24H18N4O2
(M+) 394.1430, found 394.1427.
9,12-Dimethoxy-6-methyl-7-phenylbenzo[4,5]imidazo[1,2-a]-
benzo[4,5]imidazo[1,2-c]pyrimidine (3v). Rf = 0.53. White solid
(75 mg, 61 %); m.p. 226–228 °C. 1H NMR (500 MHz, CDCl3) δ = 2.38
(s, 3H), 3.91 (s, 3H), 4.10 (s, 3H), 6.35 (d, J = 8.5 Hz, 1H), 6.72 (d, J =
8.5 Hz, 1H), 7.53–7.58 (m, 4H), 7.66–7.73 (m, 3H), 7.97–8.01 (m, 1H),
8.82–8.86 (m, 1H); 13C NMR (125 MHz, CDCl3) δ = 13.5, 56.5, 57.4,
112.8, 115.0, 119.3, 119.6, 121.8, 123.9, 124.2, 125.4, 129.2, 129.6,
129.7, 129.9, 130.5, 131.8, 134.2, 137.5, 142.3, 144.1, 147.1, 148.3.
HRMS (EI) calcd. for C25H20N4O2 (M+) 408.1586, found 428.1587.
7,11,14-Trimethoxybenzo[4,5]imidazo[1,2-a]benzo[4,5]imid-
azo[1,2-c]quinazoline (3p). Rf = 0.53. White solid (85 mg, 71 %);
m.p. 262–264 °C. H NMR (500 MHz, CDCl3) δ = 3.91 (s, 3H), 3.97 (s,
3H), 3.99 (s, 3H), 6.67 (d, J = 8.8 Hz, 1H), 6.78 (d, J = 8.8 Hz, 1H),
7.25 (dd, J = 9.1 and 2.9 Hz, 1H), 7.53–7.55 (m, 1H), 7.87–7.9 (m,
1H), 8.01 (d, J = 7.9 Hz, 1H), 8.06 (d, J = 2.9 Hz, 1H), 8.19 (d, J =
9.1 Hz, 1H), 8.72–8.76 (m, 1H); 13C NMR (125 MHz, CDCl3) δ = 56.3,
57.0, 57.1, 112.2, 115.5, 117.5, 121.9, 123.2, 125.2, 126.6, 127.9, 128.9,
129.1, 129.9, 130.7, 132.8, 137.4, 137.7, 140.6, 142.8, 146.4, 149.4,
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160.3. HRMS (EI) calcd. for C23H18N4O3 (M+) 398.1379, found 6-Butyl-9,12-dimethoxy-7-phenylbenzo[4,5]imidazo[1,2-a]-
398.1376.
benzo[4,5]imidazo[1,2-c]pyrimidine (3w). Rf = 0.55. White solid
Eur. J. Org. Chem. 0000, 0–0
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