Page 139 - 《精细化工》2021年第6期

第 6 期 刘斯婕，等: 2H-噻唑[3,2-b][1,2,4]三嗪-3,7-二酮类化合物的设计、合成及生物活性 ·1201·

水中和，抽滤，得到固体用无水乙醇重结晶，抽滤 161.3 (d, J = 241.6 Hz), 159.4, 159.3, 153.76, 136.4,
干燥得 0.198 g 淡黄色固体Ⅴa，产率 54.2%，m.p.= 134.9, 134.2, 133.8, 131.8, 131.7 (d, J = 3.0 Hz), 131.2
(d, J = 7.6 Hz), 128.5, 122.8, 118.8, 115.2 (d, J =
1
188.3~189.7 ℃。 HNMR (600 MHz, DMSO-d 6 ), δ: 21.1 Hz), 35.7; HRMS (ESI), C 19 H 11 BrFN 3 O 2 S, m/Z:
8.25 (s, 1H), 7.77 (d, J = 6.7 Hz, 2H), 7.63~7.56 (m, [M+H] 理论值 445.9792；测试值 445.9792。
+
3H), 7.37 (dd, J = 8.4、5.4 Hz, 2H), 7.15 (t, J = 9.0 Hz, 6-(4-氟苄基)-2-(3-三氟甲基苯亚甲基)-2H-噻唑
13
2H), 4.02 (s, 2H); CNMR (151 MHz, DMSO-d 6 ), δ:
165.1, 161.3 (d, J = 243.1 Hz), 159.5, 153.7, 138.2, 并[3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴf）：产率 64.5%，
1
132.5, 131.8, 131.7 (d, J = 3.0 Hz), 131.2 (d, J = 7.6 m.p.=220.6~221.9 ℃。 HNMR (600 MHz, DMSO-d 6),
Hz), 130.9, 129.8, 117.0, 115.2 (d, J = 21.1 Hz), 35.8; δ: 8.38 (s, 1H), 8.18 (s, 1H), 8.03 (d, J = 7.8 Hz, 1H),
+
HRMS (ESI), C 19 H 12 FN 3 O 2 S, m/Z: [M+H] 理论值 7.94 (d, J = 7.8 Hz, 1H), 7.85 (t, J = 7.8 Hz, 1H), 7.37
366.0707；测试值 366.0712。 (dd, J = 9.0、6.0 Hz, 2H), 7.16 (t, J = 9.0 Hz, 2H), 4.02
13
(s, 2H); CNMR (151 MHz, DMSO-d 6), δ: 164.9, 161.3
6-(4- 氟苄基 )-2-(4- 氟苯 亚甲基 )-2H- 噻唑并
(d, J = 241.6 Hz), 159.4, 159.3, 153.8, 136.3, 133.6,
[3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴb）：产率 57.4%，m.p.= 133.1, 131.7 (d, J =3.0 Hz), 131.3, 131.2 (d, J =7.6 Hz),
1
204.1~205.8 ℃。 HNMR (600 MHz, DMSO-d 6 ), δ: 131.0, 130.3 (q, J =33.2 Hz), 128.2 (q, J =3.0 Hz),
8.28 (s, 1H), 7.86 (dd, J = 8.4、5.4 Hz, 2H), 7.46 (t, J = 127.7 (q, J =3.0 Hz), 123.8 (q, J =268.8 Hz), 119.3,
115.2 (d, J = 21.1 Hz), 35.8; HRMS (ESI), C 20 H 11 F 4 N 3 O 2 S,
9.0 Hz, 2H), 7.37 (dd, J = 8.4、5.4 Hz, 2H), 7.16 (t, J = +
8.4 Hz, 2H), 4.02 (s, 2H); 13 CNMR (151 MHz, m/Z: [M+H] 理论值 434.0581；测试值 434.0582。
DMSO-d 6 ), δ: 165.0, 163.7 (d, J = 253.7 Hz), 161.3 (d, 6-(4-氟苄基)-2-(4-异丙氧基苯亚甲基)-2H-噻唑
J = 241.6 Hz), 159.5, 153.7, 137.1, 133.5 (d, J = 9.1 并[3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴg）：产率 42.3%，
Hz), 131.7 (d, J = 3.0 Hz), 131.2 (d, J = 9.1 Hz), 129.3 m.p.=165.8~167.5 ℃。HNMR (600 MHz, DMSO-d 6 ),
1
(d, J = 3.0 Hz), 117.0 (d, J = 22.7 Hz), 116.7, 115.2 (d, δ: 8.20 (s, 1H), 7.74 (d, J = 9.0 Hz, 2H), 7.37 (dd, J =
J = 21.1 Hz), 35.8; HRMS (ESI), C 19 H 11 F 2 N 3 O 2 S, m/Z:
+
[M+Na] 理论值 406.0432；测试值 406.0431。 7.8、5.4 Hz, 2H), 7.16 (d, J = 9.0 Hz, 2H), 7.15 (t, J =
9.0 Hz, 2H), 4.00 (s, 2H), 3.87 (d, J = 6.6 Hz, 2H),
6-(4-氟苄基)-2-(4-甲氧基苯亚甲基)-2H-噻唑并 2.04 (m, 1H), 0.99 (d, J = 6.6 Hz, 6H); CNMR (151
13
[3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴc）：产率 48.1%，m.p.= MHz, DMSO-d 6 ), δ: 165.0, 161.8, 161.3 (d, J = 243.1
1
175.3~177.0 ℃。 HNMR (600 MHz, DMSO-d 6 ), δ: Hz), 159.6, 159.5, 153.7, 138.4, 133.4, 131.8 (d, J =
8.20 (s, 1H), 7.76 (d, J = 9.0 Hz, 2H), 7.36 (dd, J = 3.0 Hz), 131.2 (d, J = 9.1 Hz), 125.0, 115.8, 115.2 (d,
9.0、6.0 Hz, 2H), 7.15 (m, 4H), 4.00 (s, 2H), 3.86 (s, J = 22.1 Hz), 113.3, 74.2, 35.8, 27.7, 19.0; HRMS (ESI),
+
13
3H); CNMR (151 MHz, DMSO-d 6 ), δ: 165.0, 162.3, C 23 H 20 FN 3 O 3 S, m/Z: [M+Na] 理论值 460.1102；测试
161.3 (d, J = 243.1 Hz), 159.6, 159.5 153.7, 138.4, 值 460.1101。
133.3, 131.8 (d, J = 3.0 Hz), 131.2 (d, J = 7.6 Hz), 6-(4- 甲 氧基苄基 )-2- 苯亚甲 基 -2H- 噻唑 并
125.1, 115.4, 115.2 (d, J = 21.1 Hz), 113.4, 55.8, 35.8; [3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴh）：产率 47.1%，
+
HRMS (ESI), C 20 H 14 FN 3 O 3 S, m/Z: [M+H] 理论值 1
m.p.=178.6~179.9 ℃。 HNMR (600 MHz, DMSO-d 6),
396.0813；测试值 396.0808。 δ: 8.24 (s, 1H), 7.77~7.59 (m, 5H), 7.25 (d, J = 8.6 Hz,
6-(4-氟苄基)-2-(3-甲基苯亚甲基)-2H-噻唑并 2H), 6.88 (d, J = 8.6 Hz, 2H), 3.94 (s, 2H), 3.72 (s,
13
[3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴd）：产率 48.3%，m.p.= 3H); CNMR (151 MHz, DMSO-d 6 ), δ: 165.0, 159.5,
1
185.9~187.4 ℃。 HNMR (600 MHz, DMSO-d 6 ), δ: 159.5, 158.3, 154.0, 138.0, 132.6, 131.8, 130.9, 130.4,
8.20 (s, 1H), 7.57 (d, J = 6.6 Hz, 2H), 7.50 (t, J = 7.8 129.7, 127.3, 117.1, 113.9, 55.08, 35.7; HRMS (ESI),
+
Hz, 1H), 7.41 (d, J = 7.8 Hz, 1H), 7.37 (dd, J = 9.0、 C 20 H 15 N 3 O 3 S, m/Z: [M+H] 理论值 378.0907；测试值
6.0 Hz, 2H), 7.15 (t, J = 9.0 Hz, 2H), 4.01 (s, 2H), 378.0908。
13
2.40 (s, 3H); CNMR (151 MHz, DMSO-d 6), δ: 165.1, 6-(4-甲氧基苄基)-2-(4-氟苯亚甲基)-2H-噻唑并
161.3 (d, J = 243.1 Hz), 159.5, 153.7, 139.2, 138.3, [3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴi）：产率 63.2%，m.p.=
132.6, 132.5, 131.7 (d, J = 3.0 Hz), 131.3, 131.2 (d, J = 208.3~209.9 ℃。 HNMR (600 MHz, DMSO-d 6 ), δ:
1
7.55 Hz), 129.7, 128.0, 116.8, 115.2 (d, J = 21.1 Hz),
35.8, 21.0; HRMS (ESI), C 20 H 14 FN 3 O 2 S, m/Z: [M+H] + 8.26 (s, 1H), 7.85 (dd, J = 8.4、5.4 Hz, 2H), 7.45 (t, J =
理论值 380.0864；测试值 380.0865。 8.7 Hz, 2H), 7.25 (d, J = 8.5 Hz, 2H), 6.87 (d, J = 8.6 Hz,
13
2H), 3.94 (s, 2H), 3.72 (s, 3H); CNMR (151 MHz,
6-(4- 氟苄基 )-2-(3- 溴苯 亚甲基 )-2H- 噻唑并
DMSO-d 6 ), δ: 165.0, 163.7 (d, J = 226.5 Hz), 159.5,
[3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴe）：产率 59.7%，m.p.= 158.3, 154.0, 137.0, 133.5 (d, J = 9.1 Hz), 130.4, 129.3,
1
211.2~213.4 ℃。 HNMR (600 MHz, DMSO-d 6 ), δ: 127.3, 116.9 (d, J = 22.7 Hz), 116.8 (d, J = 3.0 Hz) ,
8.24 (s, 1H), 8.00 (s, 1H), 7.78 (d, J = 7.8 Hz, 1H), 113.9, 55.1, 35.7; HRMS (ESI), C 20 H 14 FN 3 O 3 S, m/Z:
+
7.74 (d, J = 7.8 Hz, 1H), 7.56 (t, J = 7.8 Hz, 1H), 7.37 [M+H] 理论值 396.0813；测试值 396.0810。
(dd, J = 8.4、5.4 Hz, 2H), 7.15 (t, J = 9.0 Hz, 2H), 4.01 6-(4-甲氧基苄基)-2-(4-氯苯亚甲基)-2H-噻唑并
13
(s, 2H); CNMR (151 MHz, DMSO-d 6 ), δ: 164.9, [3,2-b]-1,2,4-三嗪-3,7-二酮（Ⅴj）：产率 60.7%，m.p.=