10.1002/ejoc.202001280
European Journal of Organic Chemistry
FULL PAPER
7.85 (m, 1H), 7.82-7.76 (m, 1H), 7.52-7.45 (m, 2H). 13C NMR (DMSO-d6,
4-(4-Nitrophenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline B10 (CAS No.:
1537188-91-2): Flash column chromatography eluent (petroleum
ether/ethyl acetate = 5:2); 78% yield (113 mg); white solid; m.p. 263.5 oC
1
125 MHz): δ = 163.6 (d, J = 247.7 Hz, JCF), 148.3, 144.0, 137.4, 132.9
4
3
(d, J = 2.4 Hz, JCF), 131.5 (d, J = 8.8 Hz, JCF), 129.8, 129.7, 127.4,
122.7, 115.6 (d, J = 21.5 Hz, 2JCF). IR (KBr): ν = 3482.0, 3044.8, 2936.7,
2827.4, 1638.1, 1603.1, 1503.3, 1356.3, 1233.6, 1158.8, 1085.1, 996.7,
842.4, 764.6, 664.4 cm-1. HRMS (+ESI): m/z calculated for C15H10N4F
[M+H]+, 265.0889, found 265.0903.
[5]
(lit. m.p.: 256-258 oC); 1H NMR (DMSO-d6, 600 MHz): δ = 9.10 (s, 2H),
8.47 (d, J = 8.2Hz, 2H), 8.43 (d, J = 7.8Hz, 1H), 8.28 (d, J = 8.7Hz, 1H),
7.93-7.81 (m, 2H). 13C NMR (DMSO-d6, 150 MHz): δ = 148.2, 146.7,
143.7, 142.0, 137.1, 130.1, 129.9, 128.2, 123.6, 122.7, 115.5. IR (KBr): ν
= 3386.5, 3088.8, 2924.8, 2840.5, 1640.3, 1607.1, 1571.9, 1500.5,
1452.7, 1339.0, 1294.9, 1099.1, 914.3, 831.2, 693.9 cm-1. HRMS (+ESI):
m/z calculated for C16H9N5O2 [M+H]+, 292.0756, found 292.0760.
4-(4-Chlorophenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline B5 (CAS No.:
1537188-88-7): Flash column chromatography eluent (petroleum
ether/ethyl acetate = 5:1); 93% yield (131 mg); white solid; m.p. 251.9 oC
[6]
(lit. m.p.: 252-254 oC); 1H NMR (DMSO-d6, 500 MHz): δ = 16.90 (br,
4-(3-Methylphenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline
B11:
Flash
1H), 8.85 (d, J = 8.4 Hz, 2H), 8.35 (d, J = 7.9 Hz, 1H), 8.18 (d, J = 8.3 Hz,
column chromatography eluent (petroleum ether/ethyl acetate = 5:1);
93% yield (121 mg); orange solid; m.p. 197.6 oC; 1H NMR (DMSO-d6,
500 MHz): δ = 16.02 (br, 1H), 8.65 (s, 2H), 8.42 (d, J = 8.1 Hz, 1H), 8.25
(d, J = 8.2 Hz, 1H), 7.89-7.83 (m, 1H), 7.80-7.75 (m, 1H), 7.55-7.50 m,
1H), 7.41 (d, J = 7.4 Hz, 1H ), 2.48 (s, 3H). 13C NMR (DMSO-d6, 125
MHz): δ = 149.5, 144.1, 137.7, 136.5, 131.1, 129.7, 129.7, 129.6, 128.5,
127.3, 126.6, 122.7, 21.2. IR (KBr): ν = 3510.0, 3150.1, 2937.6, 2864.0,
1630.0, 1585.0, 1515.6, 1446.1, 1343.9, 1209.1, 1074.2, 984.3, 771.9,
735.1, 694.2 cm-1. HRMS (+ESI): m/z calculated for C16H13N4 [M+H]+,
261.1140, found 261.1160.
1H), 7.84-7.79 (m, 1H), 7.77-7.72 (m, 1H), 7.66 (d, J = 8.7 Hz, 2H). 13
C
NMR (DMSO-d6, 125 MHz): δ = 148.0, 143.9, 135.4, 135.2, 130.8, 129.8,
129.7, 128.7, 127.6, 122.7, 115.3. IR (KBr): ν = 3444.2, 3135.1, 2932.5,
2870.6, 1646.3, 1593.5, 1491.8, 1460.7, 1354.9, 1236.7, 1090.0, 997.0,
837.1, 760.9 664.0 cm-1. HRMS (+ESI): m/z calculated for C15H10ClN4
[M+H]+, 281.0589, found 281.0596.
4-(4-Bromophenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline B6 (CAS No.:
1537188-89-8): Flash column chromatography eluent (petroleum
ether/ethyl acetate = 5:1); 95% yield (155 mg); white Solid; m.p. 252.4 oC
[6]
(lit. m.p.: 247-249 oC); 1H NMR (DMSO-d6, 500 MHz): δ = 17.00 (br,
4-(2-Methylphenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline
B12:
Flash
1H), 8.84 (d, J = 5.5 Hz, 2H), 8.43 (d, J = 8.1 Hz, 1H), 8.26 (d, J = 8.1 Hz,
1H), 7.91-7.85 (m, 3H), 7.84-7.78 (m, 1H). 13C NMR (DMSO-d6, 125
MHz): δ = 148.2, 144.0, 135.5, 131.7, 131.1, 129.9, 129.8, 127.7, 124.4,
122.8, 115.5. IR (KBr): ν = 3372.9, 3091.2, 2920.1, 2855.6, 2663.1,
1638.1, 1585.0, 1486.9, 1421.9, 1356.0, 1209.0, 1070.2, 984.3, 834.3,
761.6 cm-1. HRMS (+ESI): m/z calculated for C15H10BrN4 [M+H]+,
325.0083, found 325.0094.
column chromatography eluent (petroleum ether/ethyl acetate = 5:1);
o
90% yield (117 mg); white solid; m.p. 225.4 C; 1H NMR (DMSO-d6, 500
MHz): δ = 16.68 (br, 1H), 8.45 (d, J = 7.8 Hz, 1H), 8.20 (d, J = 8.4 Hz,
1H), 7.86-7.81 (m, 1H), 7.80-7.75 (m, 1H), 7.70 (d, J = 7.4 Hz, 1H), 7.47-
7.36 (m, 3H), 2.34 (s, 3H). 13C NMR (DMSO-d6, 125 MHz): δ = 152.9,
144.1, 136.6, 136.6, 130.7, 130.5, 129.6, 129.2, 127.6, 125.6, 122.7,
115.3, 20.2. IR (KBr): ν = 3248.1, 2921.2, 2627.0, 2553.5, 2492.2, 1642.2,
1564.6, 1523.7, 1462.4, 1360.3, 1230.0, 1200.9, 976.2, 767.7, 730.9 cm-
1. HRMS (+ESI): m/z calculated for C16H13N4 [M+H]+, 261.1135, found
261.1145.
4-(4-(Trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline
B7:
Flash column chromatography eluent (petroleum ether/ethyl acetate =
5:1); 91% yield (143 mg); yellowish solid; m.p. 224.2 oC; 1H NMR
(DMSO-d6, 500 MHz): δ = 17.05 (br, 1H), 9.06 (d, J = 6.8 Hz, 2H), 8.45 (d,
J = 7.6 Hz, 1H), 8.30 (d, J = 8.1 Hz, 1H), 8.03 (d, J = 8.3 Hz, 1H), 7.93-
7.88 (m, 1H), 7.86-7.82 (m, 1H). 13C NMR (DMSO-d6, 125 MHz): δ =
4-(3-Bromo-5-methylphenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline B13:
Flash column chromatography eluent (petroleum ether/ethyl acetate =
5:1); 87% yield (148 mg); white solid; m.p. 281.0 oC; 1H NMR (DMSO-d6,
500 MHz): δ = 16.91 (br, 1H), 8.81 (s, 1H), 8.64 (s, 1H), 8.38 (d, J = 7.8
Hz, 1H), 8.23 (d, J = 8.2 Hz, 1H), 7.87-7.83 (m, 1H), 7.79-7.76 (m, 1H),
7.60 (s, 1H) , 2.47 (s, 3H). 13C NMR (DMSO-d6, 125 MHz): δ = 147.6,
143.8, 140.6, 138.5, 133.5, 129.9, 129.8, 128.8, 128.6, 127.7, 122.7,
121.7, 20.9. IR (KBr): ν = 3442.1, 3052.8, 2923.7, 2550.3, 1637.2, 1590.8,
1498.6, 1454.5, 1296.0, 1216.2, 1171.2, 1096.1, 959.9, 775.9, 747.4 cm-
1. HRMS (+ESI): m/z calculated for C16H12N4Br [M+H]+, 339.0245, found
339.0256.
2
147.7, 143.9, 140.1, 137.2, 130.2 (q, J = 31.9 Hz, JCF), 129.9, 129.9,
3
1
129.8, 128.0, 125.5 (q, J = 3.8 Hz, JCF), 124.2 (q, J = 272.3 Hz, JCF),
122.7. IR (KBr): ν = 3374.8, 3088.7, 2766.0, 2659.7, 1634.1, 1564.6,
1523.7, 1425.7, 1319.4, 1164.1, 1127.4, 1057.9, 980.3, 853.6, 767.8 cm-
1. HRMS (+ESI): m/z calculated for C16H10F3N4 [M+H]+, 315.0852, found
315.0864.
4-(4-Methoxycarbonylphenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline B8:
Flash column chromatography eluent (petroleum ether/ethyl acetate =
5:2); 77% yield (117 mg); yellowish solid; m.p. 249.7 oC; 1H NMR
(DMSO-d6, 500 MHz): δ = 16.97 (br, 1H), 8.95 (d, J = 6.8 Hz, 2H), 8.40 (d,
J = 6.3 Hz, 1H), 8.24 (d, J = 7.4 Hz, 1H), 8.20-8.14 (m, 2H), 7.89-7.83 (m,
1H), 7.82-7.76 (m, 1H), 3.91 (s, 3H). 13C NMR (DMSO-d6, 125 MHz): δ =
166.0 148.1, 144.0, 140.6, 137.2, 130.9, 129.9, 129.9, 129.4, 127.9,
122.8, 115.5, 52.3. IR (KBr): ν = 3203.5, 3020.7, 2953.6, 2845.3, 1687.2,
1607.8, 1491.1, 1442.0, 1323.5, 1286.7, 1200.3, 1114.1, 948.3, 775.2,
726.9 cm-1. HRMS (+ESI): m/z calculated for C17H13N4O2 [M+H]+,
305.1033, found 305.1040.
4-(Naphthalen-1-yl)-1H-[1,2,3]triazolo[4,5-c]quinoline B14 (CAS No.:
2251704-60-4): Flash column chromatography eluent (petroleum
ether/ethyl acetate = 5:1); 79% yield (117 mg); orange solid; m.p. 227.2
[6]
o
oC (lit. mp: 235-237 C); 1H NMR (DMSO-d6, 500 MHz): δ = 16.93 (br,
1H), 8.51 (s, 1H), 8.26 (d, J = 8.4 Hz, 1H), 8.16 (d, J = 8.4 Hz, 1H), 8.08
(d, J = 8.2 Hz, 2H), 8.01 (d, J = 7.3 Hz, 1H), 7.92-7.82 (m, 2H), 7.76-7.71
(m, 1H), 7.60-7.56 (m, 1H), 7.51-7.45 (m, 1H). 13C NMR (DMSO-d6, 125
MHz): δ = 144.2, 134.1, 133.5, 132.9, 131.0, 130.7, 129.7, 128.6, 128.3,
127.7, 127.5, 126.6, 126.2, 126.1, 125.7, 125.5, 125.2, 124.9, 122.9. IR
(KBr): ν = 3446.5, 3102.7, 2973.4, 2755.3, 1627.4, 1600.2, 1595.1,
1510.0, 1458.5, 1394.4, 1259.1, 1164.3, 957.7, 779.0, 732.2 cm-1. HRMS
(+ESI): m/z calculated for C19H13N4 [M+H]+, 297.1135, found 297.1138.
4-(4-Cyanophenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline
B9:
Flash
column chromatography eluent (petroleum ether/ethyl acetate = 5:2);
o
1
85% yield (115 mg); white solid; m.p. 263.5 C; H NMR (DMSO-d6, 500
MHz): δ = 16.79 (br, 1H), 8.93 (d, J = 8.4 Hz, 2H), 8.34 (d, J = 8.0 Hz,
1H), 8.17 (d, J = 8.6 Hz, 1H), 8.02 (d, J = 8.5 Hz, 2H), 7.85-7.80 (m, 1H),
7.79-7.73 (m, 1H). 13C NMR (DMSO-d6, 125 MHz): δ = 147.2, 143.8,
140.3, 137.1, 132.5, 129.9, 129.6, 128.1, 122.7, 118.7, 115.4, 112.6. IR
(KBr): ν = 3480.2, 3198.9, 2922.8, 2864.3, 2185.6, 1617.8, 1563.9,
1492.1, 1322.1, 1286.7, 1202.7, 1161.8, 1008.3, 852.2, 749.8 cm-1.
HRMS (+ESI): m/z calculated for C16H10N5 [M+H]+, 272.0936, found
272.0951.
4-(Furan-2-yl)-1H-[1,2,3]triazolo[4,5-c]quinoline B15: Flash column
chromatography eluent (petroleum ether/ethyl acetate = 5:1); 78% yield
o
1
(92 mg); brown solid; m.p. 281.9 C; H NMR (DMSO-d6, 500 MHz): δ =
16.94 (br, 1H), 8.38 (s, 1H), 8.19 (d, J = 8.3 Hz, 1H), 8.09 (s, 1H), 8.05 (s,
1H), 7.87-7.81 (m, 1H), 7.78-7.72 (m, 1H), 6.88-6.83 (m, 1H). 13C NMR
(DMSO-d6, 125 MHz): δ = 150.0, 146.0, 144.2, 129.9, 129.4, 127.3,
122.7, 112.7. IR (KBr): ν = 3395.4, 3150.1, 2924.1, 2856.5, 1608.3,
1556.9, 1445.9, 1389.9, 1255.0, 1156.8, 1040.0, 1004.1, 916.8, 844.9,
5
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