Paper
NJC
7.65 (d, J = 7.36 Hz, 1H), 7.58 (t, J = 8.08 Hz, 1H), 7.30 (d, J = 6.8 Hz,
C
21H15BrN3: m/z 388.0448; found: 388.0448; IR (cmꢀ1, KBr):
1H), 7.23 (t, J = 7.44 Hz, 1H), 7.10 (d, J = 8.32 Hz, 1H), 6.68 (t, J = 3385, 1676, 1502, 1363, 615.
6.92 Hz, 1H), 3.62 (s, 3H), 2.82 (s, 3H); 13C NMR (100 MHz, CDCl3)
d 157.0, 150.0, 146.5, 145.6, 131.3, 131.1, 129.3, 128.5, 128.2, 127.7,
10-Methyl-6-phenylpyrido[20,10:2,3]imidazo[4,5-c]quinoline (6n)
126.3, 124.7, 122.8, 122.0, 121.8, 111.7, 111.0, 55.5, 17.6; MS (GC- Yield = 0.27 g, 89%; white solid; Rf = 0.71 (40%EtOAc/n-hexane);
MS) 339; HRMS (EI, m/z) calcd for C22H17N3O: m/z 339.1372; 1H NMR (400 MHz, CDCl3) d 9.3 (s, 1H), 8.77 (d, J = 7.96 Hz, 1H),
found: 339.1370; IR (cmꢀ1, KBr): 2924, 1606, 1516, 1344, 804.
8.35 (d, J = 8.28 Hz, 1H), 7.95 (s, 1H), 7.84 (t, J = 7.32 Hz, 1H),
7.77 (d, J = 4.56 Hz, 1H), 7.67 (d, J = 7.32 Hz, 1H), 7.58 (t, J =
6.52 Hz, 1H), 6.83 (d, J = 6.96 Hz, 1H), 2.51, (s, 3H); 13C NMR
(100 MHz, CDCl3) d 149.6, 146.2, 144.8, 142.4, 135.2, 133.3,
6-(4-Methoxyphenyl)-11-methylpyrido[20,10:2,3]imidazo[4,5-c]quinoline
(6j)
Yield = 0.31 g, 92%; white solid; Rf = 0.63 (40%EtOAc/n-hexane); 132.4, 131.4, 130.9, 128.8, 127.2, 126.1, 123.3, 122.5, 119.7,
1H NMR (400 MHz, CDCl3) d 8.84 (d, J = 7.36 Hz, 1H), 8.32 (d, J = 119.6, 1175, 115.8, 22.1; MS (GC-MS) 309; HRMS (ESI, m/z)
8.12 Hz, 1H), 8.02 (d, J = 6.96 Hz, 1H), 7.76 (t, J = 7.12 Hz, 1H), calcd for C21H16N3: m/z 310.1344; Found: 310.1342; IR (cmꢀ1, KBr):
7.71 (d, J = 7.52 Hz, 1H), 7.67 (d, J = 8.56 Hz, 2H), 7.32 (d, J = 6.68 Hz, 3053, 1568, 1622, 1361, 765.
1H), 7.15 (d, J = 8.56 Hz, 2H), 6.71 (t, J = 6.92 Hz, 1H), 3.94 (s, 3H),
10-Methyl-6-(p-tolyl)pyrido[20,10:2,3]imidazo[4,5-c]quinoline (6o)
2.82 (s, 3H); 13C NMR (100 MHz, CDCl3) d 160.7, 148.0, 130.2, 129.1,
128.8, 128.5, 128.1, 126.3, 125.0, 122.8, 121.5, 121.0, 114.6, 111.9, Yield = 0.29 g, 90%; white solid; Rf = 0.61 (40%EtOAc/n-hexane);
55.5, 17.6; MS (GC-MS) 339; HRMS (ESI, m/z) calcd for C22H18N3O: 1H NMR (400 MHz, CDCl3) d 8.82 (d, J = 8.04 Hz, 1H), 8.54 (d, J =
m/z 340.1450; found: 340.1452; IR (cmꢀ1, KBr): 2841, 1641, 1581, 8.4 Hz, 1H), 8.11 (d, J = 7.12 Hz, 1H), 7.96 (t, J = 7.24 Hz, 1H),
1355, 771.
7.91(s, 1H), 7.87 (t, J = 7.72 Hz, 1H), 7.69 (d, J = 7.96 Hz, 2H),
7.51 (d, J = 7.76 Hz, 2H), 6.91 (d, J = 7.04 Hz, 1H), 2.59 (3H), 2.54
(3H); 13C NMR (100 MHz, CDCl3) 155.0, 146.8, 144.5, 139.6,
138.4, 132.2, 130.5, 128.9, 128.6, 127.5, 126.7, 125.6, 123.4,
11-Methyl-6-(3,4,5-
trimethoxyphenyl)pyrido[20,10:2,3]imidazo[4,5-c]quinoline (6k)
Yield = 0.35 g, 90%; white solid; Rf = 0.74 (40%EtOAc/n-hexane); 120.3, 119.4, 117.4, 116.7, 22.1, 21.7; MS (GC-MS) 323; HRMS
1H NMR (400 MHz, CDCl3) d 8.85 (d, J = 7.96 Hz, 1H), 8.34 (EI, m/z) calcd for C22H17N3: m/z 323.1422; Found: 323.1420; IR
(s, 1H), 7.98 (d, J = 6.88 Hz, 1H), 7.79 (t, J = 8.24 Hz, 1H), 7.72 (cmꢀ1, KBr): 3051, 2922, 1622, 1568, 819.
(t, J = 7.96 Hz, 1H), 7.35 (d, J = 6.68 Hz, 1H), 6.91 (s, 2H), 6.75
6-(4-Methoxyphenyl)-10-methylpyrido[20,10:2,3]imidazo[4,5-c]quinoline
(t, J = 6.92 Hz, 1H), 3.96 (s, 3H), 3.89 (s, 6H), 2.83 (3H); 13C NMR
(6p)
(100 MHz, CDCl3) d 154.0, 152.7, 144.0, 141.9, 133.3, 132.2, 129.2,
128.2, 126.8, 125.1, 124.5, 123.8, 122.9, 121.0, 120.7, 112.4, 105.7, Yield = 0.30 g, 90%; white solid; Rf = 0.61 (40%EtOAc/n-hexane);
61.0, 56.3, 17.6; MS (GC-MS) 399; HRMS (EI, m/z) calcd for 1H NMR (400 MHz, CDCl3) d 8.74 (d, J = 8.04 Hz, 1H), 8.28 (d, J =
C24H21N3O3: m/z 399.1583; found: 399.1580; IR (cmꢀ1, KBr): 8.24 Hz, 1H), 8.01 (d, J = 7.12 Hz, 1H), 7.77 (t, J = 8.36 Hz, 1H),
2916, 1641, 1354, 1581, 794.
7.70 (d, J = 7.92 Hz, 1H), 7.67 (d, J = 8.56 Hz, 3H), 7.15 (d, J =
8.64 Hz, 2H), 6.63 (d, J = 7.12 Hz, 1H), 3.94 (3H), 2.48 (3H);
13C NMR (100 MHz, CDCl3) 160.7, 150.4, 147.8, 147.6, 141.8,
130.2, 129.0, 128.9, 126.3, 122.6, 121.3, 120.4, 116.3, 114.8,
11-Methyl-6-(4-nitrophenyl)pyrido[20,10:2,3]imidazo[4,5-
c]quinoline (6l)
Yield = 0.33 g, 94%; white solid; Rf = 0.74 (40%EtOAc/n-hexane); 114.7, 55.5, 21.7 MS (GC-MS) 339; HRMS (ESI, m/z) calcd for
1H NMR (400 MHz, CDCl3) d 8.85 (d, J = 7.96 Hz, 1H), 8.35 (d, J = 22H18N3O: m/z 340.1450; Found: 340.1451; IR (cmꢀ1, KBr):
C
8.12 Hz, 1H), 8.20 (d, J = 8.04 Hz, 1H), 7.88 (t, J = 7.36 Hz, 1H), 3059, 1656, 1593, 702.
7.82–7.72 (m, 3H), 7.67 (d, J = 7.32 Hz, 1H), 7.51 (d, J = 6.84 Hz,
10-Methyl-6-(3,4,5-trimethoxyphenyl)pyrido[20,10:2,3]imidazo[4,5-c]-
quinoline (6q)
1H), 7.31 (d, J = 6.76 Hz, 1H), 6.68 (t, J = 6.92 Hz, 1H), 3.18 (s,
3H); 13C NMR (100 MHz, CDCl3) d150.1, 148.1, 146.8, 144.6,
134.2, 131.7, 130.6, 129.3, 128.8, 128.5, 128.4, 126.8, 125.2, Yield = 0.35 g, 88%; white solid; Rf = 0.61 (40%EtOAc/n-hexane);
123.5, 122.9, 122.0, 112.5, 17.6; MS (GC-MS) 354; HRMS (EI, 1H NMR (400 MHz, CDCl3) d 8.79 (d, J = 7.56 Hz, 1H), 8.51 (d, J =
m/z) calcd for C21H14N4O2: m/z 354.1117; found: 354.1194; IR 8.4 Hz, 1H), 8.11 (d, J = 7.04 Hz, 1H), 7.94 (d, J = 7.36 Hz, 1H),
(cmꢀ1, KBr): 1649, 1591, 1363, 1176, 769.
7.90 (d, J = 8.36 Hz, 1H), 7.84 (t, J = 7.4 Hz, 1H), 6.99 (s, 2H), 6.88
(d, J = 7.08 Hz, 1H), 3.99 (3H), 3.90 (6H), 2.58 (3H); 13C NMR
(100 MHz, CDCl3) 154.3, 146.5, 145.5, 140.6, 131.6, 128.3, 126.8,
124.5, 123.2, 119.9, 117.1, 116.6, 106.0, 61.6, 56.5, 22.1 MS (GC-MS)
6-(2-Bromophenyl)-11-methylpyrido[20,10:2,3]imidazo[4,5-c]quinoline
(6m)
Yield = 0.34 g, 89%; white solid; Rf = 0.63 (40%EtOAc/n-hexane); 399; HRMS (ESI, m/z) calcd for C24H22N3O3: m/z 400.1661; Found:
1H NMR (400 MHz, CDCl3) d 8.76 (d, J = 7.68 Hz, 1H), 8.29 (d, J = 400.1662; IR (cmꢀ1, KBr): 3061, 2852, 1687, 1595, 775.
7.8 Hz, 1H), 7.88 (d, J = 6.36 Hz, 1H), 7.76 (d, J = 7.52 Hz, 1H),
6-(2-Bromophenyl)-10-methylpyrido[20,10:2,3]imidazo[4,5-c]quinoline
(6r)
7.70–7.61 (m, 6H), 6.60 (s, 1H), 2.46 (s, 3H); 13C NMR (100 MHz,
CDCl3) d 150.2, 147.8, 147.6, 144.9, 141.7, 138.2, 129.6, 129.4,
129.2, 128.8, 128.7, 126.4, 126.2, 122.6, 121.4, 120.3, 116.2, Yield = 0.35 g, 92%; white solid; Rf = 0.69 (40%EtOAc/
1
114.8, 21.7; MS (GC-MS) 387; HRMS (ESI, m/z) calcd for n-hexane); H NMR (400 MHz, CDCl3) d 8.83 (d, J = 7.96 Hz, 1H),
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
New J. Chem., 2021, 45, 3280ꢀ3289 | 3287