Molecules 2018, 23, 746
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2H), 5.49 (s, 1H), 5.12 (s, 1H), 4.28 (t, J = 6.5 Hz, 2H), 2.13 (s, 3H), 1.77–1.60 (m, 2H), 0.92 (t, J = 7.4 Hz, 3H);
13C NMR (100 MHz, DMSO-d6)
δ (ppm): 151.65, 151.17, 145.70, 145.25, 142.78, 132.17, 131.23, 130.55, 125.61,
120.30, 115.28, 114.40, 69.45, 48.40, 22.00, 20.36, 10.59; EI-MS (m/z): 364, found 364 [M]+.
Isopropyl 1-oxo-3-(4-tolyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-d][1,2,4]triazine-2(1H)-carboxylate (4q): yellow
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powder; yield 28.6%; m.p. 165.7–167.6 C; IR (KBr, cm−1) v: 1784, 1713, 1613, 1569; 1H NMR (400 MHz,
DMSO-d6)
δ (ppm): 7.96 (d, 1H), 7.67 (d, J = 6.1, 2.5 Hz, 1H), 7.46–7.30 (m, 2H), 7.08 (d, J = 8.4 Hz, 2H),
6.95 (d, J = 8.5 Hz, 2H), 5.47 (s, 1H), 5.21–4.98 (m, 2H), 2.13 (s, 3H), 1.32 (d, J = 5.2 Hz, 6H); 13C NMR
(100 MHz, DMSO-d6)
δ (ppm): 151.18, 151.10, 145.72, 145.29, 142.80, 132.13, 131.25, 130.55, 125.58,
120.29, 115.25, 114.40, 72.52, 48.38, 22.01, 20.36; EI-MS (m/z): 364, found 364 [M]+.
Isobutyl 1-oxo-3-(4-tolyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-d][1,2,4]triazine-2(1H)-carboxylate (4r): white powder;
◦
1
yield 35.3%; m.p. 115.7–116.8 C; IR 1785, 1751, 1617, 1572; H NMR (400 MHz, DMSO-d6)
δ (ppm):
7.96 (dd, J = 6.3, 2.6 Hz, 1H), 7.67 (dd, J = 6.1, 2.6 Hz, 1H), 7.37 (pd, J = 7.4, 3.7 Hz, 2H), 7.08 (d, J = 8.5 Hz,
2H), 6.95 (d, J = 8.7 Hz, 2H), 5.49 (s, 1H), 5.13 (s, 1H), 4.11 (d, J = 6.5 Hz, 2H), 2.14 (s, 3H), 2.03–1.89 (m, 1H),
0.93 (d, J = 6.7 Hz, 6H); 13C NMR (100 MHz, DMSO-d6)
δ (ppm): 151.64, 151.17, 145.72, 145.26, 142.79,
132.18, 131.24, 130.55, 125.62, 120.29, 115.28, 114.42, 73.57, 48.46, 27.83, 20.37, 19.43, 19.11; EI-MS (m/z): 378,
found 378 [M]+.
Phenyl 1-oxo-3-(4-tolyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-d][1,2,4]triazine-2(1H)-carboxylate (4s): white powder;
yield 37.3%; m.p. 184.2–185.6 ◦C; IR (KBr, cm−1) v: 1749, 1569, 1510, 1453; 1H NMR (400 MHz, DMSO-d6)
δ
(ppm): 7.98 (dd, J = 6.5, 2.5 Hz, 1H), 7.71 (dd, J = 6.2, 2.2 Hz, 1H), 7.54–7.46 (m, 2H), 7.40 (ddd, J = 5.9,
5.3, 3.7 Hz, 2H), 7.35 (t, J = 7.0 Hz, 3H), 7.16–7.07 (m, 4H), 5.58 (s, 1H), 5.32 (s, 1H), 2.16 (s, 3H); 13C NMR
(100 MHz, DMSO-d6) δ (ppm): 151.12, 150.73, 145.49, 145.04, 142.79, 132.43, 131.79, 130.70, 130.26, 127.01,
125.82, 122.06, 120.42, 115.40, 114.44, 48.29, 20.40; EI-MS (m/z): 398, found 398 [M]+.
Ethyl 1-oxo-3-(4-fluorophenyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-d][1,2,4]triazine-2(1H)-carboxylate (4t): yellow
powder; yield 31.1%; m.p. 159.9–161.5 ◦C; IR (KBr, cm−1) v: 1784, 1709, 1615, 1569; 1H NMR (400 MHz,
DMSO-d6)
δ (ppm): 7.96 (d, J = 7.0 Hz, 1H), 7.67 (t, J = 13.3 Hz, 1H), 7.49–7.29 (m, 2H), 7.23–6.99 (m, 4H),
5.52 (s, 1H), 5.16 (s, 1H), 4.37 (q, J = 6.9 Hz, 2H), 1.40–1.24 (m, 3H); 13C NMR (100 MHz, DMSO-d6)
δ
(ppm): 151.49, 150.99, 145.52, 143.96, 142.78, 131.28, 125.70, 120.36, 117.13, 116.90, 116.68, 114.44, 64.35,
48.54, 14.57; EI-MS (m/z): 354, found 354 [M]+.
Ethyl 1-oxo-3-(4-bromophenyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-d][1,2,4]triazine-2(1H)-carboxylate (4u): yellow
powder; yield 34.2%; m.p. 151.5–153.4 ◦C; IR (KBr, cm−1) v: 1590, 1487, 1451, 1437; 1H NMR (400 MHz,
DMSO-d6)
δ (ppm): 7.96 (d, J = 7.2 Hz, 1H), 7.69 (d, J = 7.1 Hz, 1H), 7.47 (d, J = 8.0 Hz, 2H), 7.43–7.33
(m, 2H), 7.07 (d, J = 8.0 Hz, 2H), 5.57 (s, 1H), 5.18 (s, 1H), 4.38 (dd, J = 13.8, 6.8 Hz, 2H), 1.31 (t, J = 6.9 Hz,
3H); 13C NMR (100 MHz, DMSO-d6)
δ (ppm): 151.35, 150.86, 146.92, 145.34, 142.76, 132.86, 131.22, 125.72,
120.36, 117.50, 115.03, 114.43, 64.42, 48.15, 14.56; EI-MS (m/z): 416, found 416 [M]+.
Methyl 1-oxo-3-(3-chlorophenyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-d][1,2,4]triazine-2(1H)-carboxylate (4v):
1
yellow powder; yield 28.9%; m.p. 196.2–198.5 ◦C; IR (KBr, cm−1) v: 1786, 1706, 1616, 1571; H NMR
(400 MHz, DMSO-d6)
δ (ppm): 7.96 (d, J = 6.8 Hz, 1H), 7.70 (d, J = 7.0 Hz, 1H), 7.40 (td, J = 12.4, 7.9 Hz,
2H), 7.35–7.27 (m, 1H), 7.23 (d, J = 1.8 Hz, 1H), 7.03 (t, J = 9.4 Hz, 2H), 5.63 (s, 1H), 5.14 (s, 1H), 3.90 (s, 3H);
13C NMR (100 MHz, DMSO-d6)
δ (ppm): 151.87, 150.85, 149.01, 145.27, 142.75, 134.90, 131.90, 131.20,
125.80, 123.00, 120.42, 115.17, 114.47, 113.83, 55.21, 48.07; EI-MS (m/z): 358, found 358 [M]+.
Methyl 1-oxo-3-phenyl-4-methyl-3,4-dihydrobenzo[4,5]imidazo[1,2-d][1,2,4]triazine-2(1H)-carboxylate (4w):
1
yellow powder; yield 26.1%; m.p. 120.0–121.9 ◦C; IR (KBr, cm−1) v: 1787, 1706, 1616, 1571; H NMR
(400 MHz, DMSO-d6)
7.30 (t, J = 7.9 Hz, 2H), 7.13 (d, J = 8.1 Hz, 2H), 6.97 (t, J = 7.2 Hz, 1H), 5.84 (dd, J = 13.4, 6.5 Hz, 1H),
3.93 (s, 3H), 1.70 (d, J = 6.8 Hz, 3H); 13C NMR (100 MHz, DMSO-d6)
(ppm): 153.56, 152.70, 147.58,
δ (ppm): 8.00 (d, J = 7.8 Hz, 1H), 7.68 (d, J = 7.0 Hz, 1H), 7.44–7.35 (m, 2H),
δ
145.33, 142.70, 131.06, 130.23, 125.82, 123.46, 120.42, 115.69, 114.63, 55.31, 53.90, 17.83; EI-MS (m/z): 336,
found 336 [M]+.