Page 182 - 《精细化工》2020年第8期

·1680· 精细化工 FINE CHEMICALS 第 37 卷

8.89(d, J= 4.2 Hz, 1H), 8.68(d, J = 8.8 Hz, 1H), 7.97(d, 1H), 9.01(d, J = 7.8 Hz, 1H), 8.92(d, J = 4.2 Hz, 1H),
J = 8.0 Hz, 2H), 7.92(d, J = 8.4 Hz, 1H), 7.56(dd, J 1 = 8.72(d, J = 9.0 Hz, 1H), 8.18~8.16(m, 2H), 7.96(d, J =
4.2 Hz, J 2 =8.8 Hz, 1H), 7.35(d, J = 8.0 Hz, 2H), 7.8 Hz, 1H), 7.81~7.78(m, 2H), 7.68(m, 2H), 7.59(dd,
4.29(q, J = 7.2 Hz, 2H), 2.45(s, 3H), 1.25(t, J = 7.2 Hz, J 1 = 4.2 Hz, J 2 = 8.4 Hz, 1H), 7.50 (m, 2H), 7.43 (m,
13
3H); CNMR (CDCl 3 , 100 MHz), δ:165.50, 164.18(t, 1H), 4.31(q, J = 7.2 Hz, 2H), 1.27(t, J = 7.2 Hz, 3H);
J = 35.0 Hz), 148.36, 142.68, 138.59, 137.57, 133.71(t, 13 CNMR (CDCl 3 , 100 MHz)，δ: 165.25, 164.19(t, J =
J = 3.7 Hz), 131.86, 129.48, 127.30, 126.86(t, J = 35.0 Hz), 148.43, 144.93, 139.85, 138.61, 137.47,
9.0 Hz), 124.73(t, J = 2.0 Hz), 122.40, 121.90(t, J= 133.78(t, J = 3.7 Hz), 133.29, 128.94, 128.11, 127.86,
24.4 Hz), 114.62, 114.06(t, J = 251.1 Hz), 63.32, 127.47, 127.19, 126.89(t, J = 9.0 Hz), 124.76(t, J =2.0 Hz),
–1
21.46, 13.78 [14] ;IR (KBr), ν/cm : 2842, 1629, 1287, 122.48, 122.08(t, J = 24.4 Hz), 114.74, 114.0(t, J =
1024;HRMS (ESI), m/Z:calcd for C 21 H 18 F 2 N 2 O 3 251.1 Hz), 63.37, 13.81 [14] ; IR(KBr)，ν/cm : 3346,
–1
+
[M+H] 385.1363, found 385.1361。 2929, 1766, 1678, 1526, 1273; HRMS (ESI), m/Z:calcd
Ⅲc：白色固体，转化率 80%，收率 47%；m.p.: for C 26H 20F 2N 2O 3 [M+H] 447.1520, found 447.1517。
+
1
146~147 ℃; HNMR (CDCl 3 , 600 MHz)，δ:10.88 (s, Ⅲg：白色固体,转化率 90%，收率 58%；m.p.:
1H), 8.94(d, J = 8.4 Hz, 1H), 8.90(d, J = 4.2 Hz, 1H), 96~97 ℃; HNMR (CDCl 3 , 600 MHz), δ: 10.89 (s,
1
8.70(d, J = 8.4 Hz, 1H), 8.02(d, J = 8.4 Hz, 2H), 7.93(d, 1H), 8.94(d, J = 8.4 Hz, 1H), 8.88(d, J = 4.2 Hz, 1H),
J = 8.4 Hz, 1H), 7.58(dd, J 1 = 4.2 Hz, J 2 = 8.4 Hz, 1H), 8.70(d, J = 9.0 Hz, 1H), 8.13(d, J = 9.0 Hz, 2H), 7.93
7.53 (d, J = 8.4 Hz, 2H), 4.30(q,J = 7.2 Hz, 2H), 1.27(t, (d, J = 8.4 Hz, 1H), 7.58(dd, J 1 = 4.2 Hz, J 2 = 8.4 Hz,
J = 7.2 Hz, 3H); 13 CNMR (CDCl 3 , 100 MHz), δ: 1H), 7.40(d, J = 8.4 Hz, 2H), 4.30(q, J = 7.2 Hz, 2H),
164.42, 164.14(t, J = 34.9 Hz), 148.49, 138.54, 138.48, 1.26(t, J = 7.2 Hz, 3H); CNMR (CDCl 3, 151 MHz), δ:
13
137.18, 133.84(t, J = 3.7 Hz), 133.04, 129.12, 128.73, 164.15, 151.95, 148.51, 138.52, 137.13, 133.86,
126.82(t, J = 8.9 Hz), 124.75(t, J = 2.1 Hz), 122.53, 133.06, 129.26, 126.81, 124.74, 122.57, 122.43,
122.36(t, J = 24.4 Hz), 114.81, 113.99(t, J = 251.2 Hz), 121.19, 120.82, 119.47, 114.82, 113.97, 112.29, 63.41,
–1
63.39, 13.80 [14] ; IR (KBr), ν/cm : 3349, 2921, 1765, 13.79; IR(KBr), ν/cm : 3349, 2929, 1769, 1685, 1536,
–1
1683, 1530, 1281; HRMS (ESI), m/Z:calcd for 1259; HRMS (ESI), m/Z:calcd for C 21 H 15 F 5 N 2 O 4
+
C 20 H 15 ClF 2 N 2 O 3 [M+H] 405.0817, found 405.0819。 +
[M+H] 455.1030, found 455.1034。
Ⅲd:白色固体，转化率 77%，收率 40%；m.p.: Ⅲh：白色固体，转化率 84%，收率 48%；m.p.:
1
137~138 ℃; HNMR (CDCl 3 , 600 MHz)，δ: 10.89(s, 152~153 ℃; HNMR (CDCl 3 , 600 MHz), δ: 10.88 (s,
1
1H), 8.94(d, J = 7.8 Hz, 1H), 8.90(d, J = 4.2 Hz, 1H), 1H), 8.95(d, J = 8.4 Hz, 1H), 8.89(d, J = 4.2 Hz, 1H),
8.70(d, J = 8.4 Hz, 1H), 7.95(d, J = 8.4 Hz, 2H), 7.93 8.69(d, J = 8.4 Hz, 1H), 8.00(d, J = 8.4 Hz, 2H), 7.92
(d, J = 8.4 Hz, 1H), 7.70(d, J = 8.4 Hz, 2H), 7.59(dd, (d, J = 8.4 Hz, 1H), 7.57(dd, J 1 = 4.2 Hz, J 2 = 8.4 Hz,
J 1 = 4.2 Hz, J 2 = 8.4 Hz, 1H), 4.30(q, J = 7.2 Hz, 2H), 1H), 7.37(d, J = 8.4 Hz, 2H), 4.29(q, J = 7.2 Hz, 2H),
13
1.26(t, J = 7.2 Hz, 3H); CNMR (CDCl 3, 100 MHz), δ: 2.55(s, 3H), 1.26(t, J = 7.2 Hz, 3H); CNMR (CDCl 3 ,
13
164.56, 164.15(t, J =34.9 Hz), 148.51, 138.57, 137.20, 151 MHz), δ: 165.05, 164.21, 148.41, 144.55, 138.58,
133.87(t, J = 3.7 Hz), 133.56, 132.13, 128.91, 126.99, 137.47, 133.80, 130.70, 127.70, 126.95, 126.89,
126.85(t, J = 9.0 Hz), 124.78(t, J = 2.0 Hz), 122.55, 126.83, 125.54, 124.75, 122.48, 122.00, 114.68,
122.42(t, J = 24.5 Hz), 114.86, 114.01(t, J = 251.2 Hz), 114.04, 63.38, 14.95, 13.82; IR (KBr), ν/cm : 3342,
–1
–1
63.39, 13.82 [14] ; IR (KBr), ν/cm : 3342, 2927, 1759, 2929, 1759, 1678, 1523, 1280. HRMS (ESI),
1678, 1523, 1273; HRMS (ESI), m/Z: calcd for m/Z:calcd for C 21 H 18 F 2 N 2 O 3 S[M+H] 417.1084, found
+
+
C 20 H 15 BrF 2 N 2 O 3 [M+H] 449.0312, found 449.0315。
417.1085。
Ⅲe：白色固体，转化率 74%，收率 36%；m.p.: Ⅲi：白色固体，转化率 69%，收率 34%；m.p.:
1
117~118 ℃; HNMR (CDCl 3 , 600 MHz), δ: 10.88(s, 163~164 ℃; HNMR (CDCl 3 , 600 MHz), δ: 10.70(s,
1
1H), 8.94(d, J = 8.4 Hz, 1H), 8.89(d, J = 4.2 Hz, 1H), 1H), 8.99(d, J = 8.4 Hz, 1H), 8.84(d, J = 4.2 Hz, 1H),
8.70(d, J = 9.0 Hz, 1H), 7.95(d, J = 8.4 Hz, 1H), 7.92 8.68(d, J = 8.4 Hz, 1H), 7.95(d, J = 8.4 Hz, 1H), 7.82
(d, J = 9.0 Hz, 2H), 7.80(d, J = 9.0 Hz, 2H), 7.58(dd, (d, J = 7.8 Hz, 1H), 7.55(dd, J 1 = 4.2 Hz, J 2 = 8.4 Hz,
J 1 = 4.2 Hz, J 2 = 8.4 Hz, 1H), 4.29(q, J = 7.2 Hz, 2H), 1H), 7.51(d, J = 8.4 Hz, 1H), 7.46(t, J = 7.2 Hz, 1H),
13
1.26(t, J = 7.2 Hz, 3H); CNMR (CDCl 3 , 100 MHz)，δ: 7.42(t, J = 7.2 Hz, 1H), 4.29(q, J = 7.2 Hz, 2H), 1.26(t,
164.76, 164.15(t, J = 34.9 Hz), 148.50, 138.56, 138.12, J = 7.2 Hz, 3H); CNMR (CDCl 3, 100 MHz), δ: 165.04,
13
137.18, 134.13, 133.86 (t, J = 3.8 Hz), 128.85, 126.84 164.16(t, J = 35.0 Hz), 148.53, 138.53, 137.29, 135.38,
(t, J = 8.9 Hz), 124.77(t, J = 2.2 Hz), 122.55, 122.40(t, 133.69(t, J = 3.7 Hz), 131.77, 131.16, 130.58, 130.20,
J = 24.4 Hz), 114.85, 114.00(t, J = 250.9 Hz), 99.32, 127.21, 126.79(t, J = 9.0 Hz), 124.76(t, J = 2.1 Hz),
–1
63.39, 13.82 [14] ; IR (KBr), ν/cm : 3342, 2919, 1766, 122.63(t, J = 24.4 Hz), 122.49, 115.14, 113.99(t, J =
–1
1678, 1526, 1280; HRMS (ESI), m/Z:calcd for 251.2 Hz), 63.39, 13.81 [14] ; IR (KBr), ν/cm : 3312,
+
C 20 H 15 F 2 IN 2 O 3 [M+H] 497.0173, found 497.0177。 2923, 1766, 1678, 1516, 1280; HRMS (ESI), m/Z:calcd
+
Ⅲf：白色固体,转化率 81%，收率 40%；m.p.: for C 20H 15ClF 2N 2O 3 [M+H] 405.0817, found 405.0820。
1
115~116 ℃; HNMR (CDCl 3 , 600 MHz)，δ: 10.99 (s, Ⅲj：白色固体, 转化率 80%，收率 41%; m.p.: