H.-Y. Wang, X.-C. Liu, Z.-B. Huang, and D.-Q. Shi
Vol 000
2.65 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3) δ: 164.6, 162.1,
157.9, 153.4, 151.0, 142.0, 135.6, 131.4, 129.2, 129.1, 124.2,
122.4, 118.3, 117.3, 1170, 111.8, 13.0; IR (KBr, cmÀ1) : 3080,
1736, 1616, 1528, 1492, 1273, 1229, 1204, 1048, 970, 854,
756 cmÀ1; HRMS (EI) calcd for C17H11F N2O2 [M]+ 294.0805;
found 294.0801.
1030, 824cmÀ1; HRMS (EI) calcd for C18H Cl N2O2 [M]+
324.0666; found 324.0666.
35
13
8-Chloro-1-(4-methoxyphenyl)-3-methylchromeno[4,3-c]
pyrazol-4(1H)-one (2k). White solid; mp 210~ 212°C; 1H NMR
(300MHz, CDCl3) δ: 7.45–7.33 (m, 4H, ArH), 7.11 (d, J =8.7Hz,
2H, ArH), 7.06–7.05 (m, 1H, ArH), 3.94 (s, 3H, OCH3), 2.67
(s, 3H, CH3); 13C NMR (100MHz, CDCl3) δ: 161.1, 157.6,
151.7, 150.8, 140.7, 131.7, 131.1, 129.4, 128.1, 122.2, 119.5,
115.2, 113.2, 108.4, 55.9, 13.0; IR (KBr, cmÀ1): 3066, 2957,
2837, 1745, 1652, 1541, 1523, 1457, 1396, 1261, 1207, 1028,
1-(3-Chlorophenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-
one (2e). White solid; mp 210 ~ 212 °C (lit.[14] 213 ~ 215 °C);
1H NMR (300 MHz, CDCl3) δ: 7.61–7.55 (m, 3H, ArH),
7.51–7.42 (m, 3H, ArH), 7.18–7.06 (m, 2H, ArH), 2.67 (s, 3H,
CH3); 13C NMR (100 MHz, CDCl3) δ: 158.0, 153.6, 151.4,
146.6, 142.1, 140.6, 135.8, 131.6, 131.1, 130.7, 127.5, 124.3,
122.6, 118.5, 111.8, 106.9, 13.1; IR (KBr, cmÀ1) : 3080, 1743,
983, 835, 820cmÀ1; HRMS (EI) calcd for C18H ClN2O3 [M]+
35
13
340.0615; found 340.0611.
8-Chloro-1-(4-chlorophenyl)-3-methylchromeno[4,3-c]
pyrazol-4(1H)-one (2l). White solid; mp 234 ~ 236 °C; 1H NMR
(300MHz, CDCl3) δ: 7.63–7.58 (m, 2H, ArH), 7.52–7.47
(m, 2H, ArH), 7.42–7.33 (m, 2H, ArH), 7.10 (s, 1H, ArH), 2.66
(s, 3H, CH3); 13C NMR (75MHz, CDCl3) δ: 157.2, 151.7, 151.3,
146.1, 137.2, 136.6, 134.3, 131.2, 130.3, 129.5, 128.1, 121.8,
119.6, 112.8, 12.8; IR (KBr, cmÀ1): 3096, 3044, 3002, 2976,
1652, 1593, 1521, 1482, 1208, 1046, 1023, 972, 875, 757 cmÀ1
;
HRMS (EI) calcd for C17H ClN2O2 [M]+ 310.0509; found
35
11
310.0509.
3-Methyl-1-(3-methylphenyl)chromeno[4,3-c]pyrazol-4
(1H)-one (2f). White solid; mp 190 ~ 192 °C (lit.[14] 202~ 203 °
C); 1H NMR (300MHz, CDCl3) δ: 7.51–7.43 (m, 4H, ArH), 7.37–
7.31 (m, 2H, ArH), 7.13 (d, J = 7.5 Hz, 1H, ArH), 7.07–7.01
(m, 1H, ArH), 2.69 (s, 3H, CH3), 2.47 (s, 3H, CH3); 13C NMR
(100MHz, CDCl3) δ: 158.2, 153.5, 150.9, 141.8, 140.5, 139.5,
131.2, 131.1, 129.8, 127.6, 124.1, 124.0, 122.8, 118.2, 112.1,
106.5, 21.6, 13.1; IR (KBr, cmÀ1) : 1746, 1671, 1648, 1616,
1522, 1490, 1047, 1020, 798, 756cmÀ1; HRMS (EI) calcd for
C18H14 N2O2 [M]+ 290.1055; found 290.1053.
1762, 1577, 1521, 1410, 1206, 1095, 1025, 985, 836cmÀ1
;
35
HRMS (ESI) calcd for C17H Cl2N2O2 [M+ H]+ 345.0198; found
11
345.0197.
8-Chloro-1-(4-fluorophenyl)-3-methylchromeno[4,3-c]
pyrazol-4(1H)-one (2m).
White solid; m.p. 218~ 220°C; 1H
NMR (300MHz, CDCl3) δ: 7.56–7.52 (m, 2H, ArH), 7.40–7.30
(m, 4H, ArH), 7.00 (d, J = 2.1Hz, 1H, ArH), 2.62 (s, 3H, CH3);
13C NMR (100 MHz, CDCl3) δ: 165.2, 161.9, 157.3, 151.7,
151.2, 140.8, 135.2, 135.1, 131.3, 129.5, 129.1, 129.0, 122.0,
120.0, 117.5, 117.2, 112.9, 112.7, 106.7, 12.9; IR (KBr, cmÀ1):
3104, 3052, 1745, 1522, 1490, 1448, 1416, 1227, 1021, 986, 896,
1-Phenyl-3-propylchromeno[4,3-c]pyrazol-4(1H)-one (2g).
White solid; mp 210 ~ 212 °C; 1H NMR (300 MHz, CDCl3)
δ: 7.61–7.55 (m, 5H, ArH), 7.45–7.42 (m, 2H, ArH), 7.11–
7.03 (m, 2H, ArH), 3.07–3.03 (m, 2H, CH2), 1.90–1.84 (m,
2H, CH2), 1.04 (t, J = 6.0 Hz, 3H, CH3); 13C NMR (100 MHz,
CDCl3) δ: 157.6, 154.7, 153.1, 141.6, 139.4, 131.0, 130.1,
130.0, 126.9, 123.9, 122.4, 117.9, 111.8, 105.8, 29.2, 21.9,
14.0; IR (KBr, cmÀ1) : 3059, 2955, 2930, 2870, 1737, 1578,
1522, 1429, 1146, 1044, 1015, 761, 619 cmÀ1; HRMS (ESI)
calcd for C19H18N2O2 [M + H]+ 305.1290; found 305.1294.
3-Propyl-1-(4-methylphenyl)chromeno[4,3-c]pyrazol-4(1H)-
834, 772 cmÀ1; HRMS (EI) calcd for C17H ClF N2O2 [M]+
35
10
328.0415; found 328.0412.
8-Chloro-3-methyl-1-(2-methylphenyl)chromeno[4,3-c]
pyrazol-4(1H)-one (2n). White solid; mp 239~ 240°C; 1H NMR
(300MHz, CDCl3) δ: 7.55 (d, J = 6.0 Hz, 1H, ArH), 7.49–7.44
(m, 2H, ArH), 7.40–7.34 (m, 3H, ArH), 6.67 (s, 1H, ArH), 2.69
(s, 3H, CH3), 2.05 (s, 3H, CH3); 13C NMR (75MHz, CDCl3)
δ: 157.3, 151.5, 150.8, 146.0, 140.9, 137.7, 136.0, 131.7, 131.0,
129.4, 127.6, 121.3, 119.3, 118.1, 112.9, 105.9, 17.2, 12.9; IR
(KBr, cmÀ1): 3090, 3000, 2931, 1748, 1577, 1428, 1126, 1019,
1
one (2h). White solid; mp 134 ~ 136 °C; H NMR (300 MHz,
CDCl3) δ: 7.46–7.42 (m, 6H, ArH), 7.11–7.03 (m, 2H, ArH),
3.05–3.01 (m, 2H, CH2), 2.50 (s, 3H, CH3), 1.89–1.83 (m, 2H,
CH2), 1.04 (t, J = 6.0 Hz, 3H, CH3); 13C NMR (75 MHz,
CDCl3) δ: 157.5, 154.4, 152.9, 141.5, 140.2, 136.8, 130.8,
130.3, 126.6, 123.7, 122.4, 11.6, 111.7, 105.5, 29.1, 21.8,
21.3, 13.9; IR (KBr, cmÀ1) : 3035, 2975, 2931, 2899, 1739,
1531, 1412, 1048, 880, 757 cmÀ1; HRMS (ESI) calcd for
C20H19N2O2 [M + H]+ 319.1447; found 319.1444.
980, 831, 771cmÀ1; HRMS (ESI) calcd for C18H ClN2O2
35
14
[M+ H]+ 325.0744; found 325.0745.
8-Bromo-3-methyl-1-(3-methylphenyl)chromeno[4,3-c]
pyrazol-4(1H)-one (2o). White solid; mp 256~ 258°C (lit.[22]
253 ~ 254 °C); H NMR (300 MHz, CDCl3) δ: 7.56–7.44 (m, 3H,
1
ArH), 7.37 (s, 1H, ArH), 7.33-7.29 (m, 2H, ArH), 7.26
8-Chloro-3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-
one (2i). White solid; mp 282 ~ 284 °C (lit.[20] 280∼283 °C);
1H NMR (300 MHz, CDCl3) δ: 7.63–7.53 (m, 5H, ArH),
7.37–7.33 (m, 2H, ArH), 7.01 (s, 1H, ArH), 2.66 (s, 3H, CH3);
13C NMR (75 MHz, CDCl3) δ: 157.4, 151.6, 150.9, 140.5,
138.8, 131.0, 130.5, 130.0, 129.2, 126.7, 122.1, 119.4, 112.9,
106.5, 12.9; IR (KBr, cmÀ1): 3092, 3069, 1752, 1543, 1522,
1483, 1378, 1207, 981, 832, 776 cmÀ1; HRMS (EI) calcd for
(t, J = 3.9Hz,1H, ArH), 2.69 (s, 3H, CH3), 2.49 (s, 3H, CH3); 13
C
NMR (100MHz, CDCl3) δ: 157.5, 152.3, 151.1, 140.7, 140.4,
138.9, 134.0, 131.4, 130.0, 127.4, 125.4, 123.8, 119.9, 116.8,
113.7, 106.7, 21.5, 13.1; IR (KBr, cmÀ1): 3095, 2925, 1756,
1609, 1519, 1487, 1455, 1208, 1018, 978, 877, 827, 770cmÀ1
;
HRMS (EI) calcd for C18H Br N2O2 [M]+ 368.0160; found
79
13
368.0163.
8-Bromo-1-(4-chlorophenyl)-3-methylchromeno[4,3-c]
pyrazol-4(1H)-one (2p). White solid; mp 242~ 243°C; 1H NMR
(300MHz, CDCl3) δ: 7.56–7.41 (m, 5H, ArH), 7.23–7.19
(m, 2H, ArH), 2.60 (s, 3H, CH3); 13C NMR (75MHz, CDCl3)
δ: 157.1, 152.0, 151.2, 140.3, 137.3, 136.4, 134.1, 130.2, 127.9,
124.8, 119.8, 116.7, 113.2, 106.7, 12.8; IR (KBr, cmÀ1): 3095,
C17H ClN2O2 [M]+ 310.0509; found 310.0504.
35
11
8-Chloro-3-methyl-1-(4-methylphenyl)chromeno[4,3-c]pyrazol-
4(1H)-one (2j). White solid; m.p. 242 ~ 244 °C; 1H NMR
(300 MHz, CDCl3) δ: 7.56–7.17 (m, 6H, ArH), 7.04 (s, 1H, ArH),
2.62 (s, 3H, CH3), 2.48 (s, 3H, CH3); 13C NMR (100 MHz,
CDCl3) δ: 157.5, 151.7, 150.9, 141.0, 140.6, 136.5, 131.1, 130.7,
129.4, 126.6, 122.3, 119.5, 113.2, 106.5, 21.6, 13.0; IR (KBr,
cmÀ1): 3034, 1750, 1699, 1648, 1576, 1541, 1508, 1489, 1207,
3001, 2976, 2935, 1761, 1578, 1520, 1439, 1095, 1026, 980,
11
79
837 cmÀ1; HRMS (ESI) calcd for C17H Br 35ClN2O2 [M+ H]+
388.9692; found 388.9692.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet