Page 91 - 《精细化工》2022年第5期

第 5 期 唐文强，等: 吲哚席夫碱类衍生物的合成及其抗 HIV-1 活性 ·945·

8.0 Hz, 1H), 7.39~7.35 (m, 1H), 7.32 (t, J = 8.0 Hz, (s, 1H), 8.89 (s, 1H), 7.60 (t, J = 2.4 Hz, 1H), 7.56 (d,
13
1H), 6.87 (d, J = 7.2 Hz, 1H); CNMR (100 MHz, 丙 J = 7.6 Hz, 2H), 7.47 (d, J = 7.6 Hz, 2H), 7.39~7.35
1
酮-d 6 ), δ: 160.4, 157.0 (d, J C — F = 248.8 Hz), 145.3, (m, 1H), 7.29 (d, J = 8.0 Hz, 1H), 7.18 (t, J = 8.4 Hz,
13
3
138.1 (d, J C — F = 10.7 Hz), 131.1, 130.2, 128.6, 124.4, 1H), 7.05 (d, J = 7.6 Hz, 1H); CNMR (100 MHz, 丙
2
3
123.4 (d, J C — F = 7.9 Hz), 117.4 (d, J C — F = 18 Hz), 酮-d 6 ), δ: 157.8, 143.5, 136.5, 130.3, 129.5, 128.3,
3
2
116.4 (d, J C — F = 27.0 Hz), 107.9, 105.8 (d, J C — F = 128.1, 125.3, 124.8, 122.9, 120.4, 109.6, 108.4; HRMS
+
(ESI), m/Z: [C 15 H 11 ClN 2 +H] 理论值 255.7250，实测
+
9.9 Hz); HRMS (ESI), m/Z: [C 15 H 11 FN 2 +H] 理论值
值 255.7248。
239.2734，实测值 239.2736。
1-(5-氯-1H-吲哚-3-基)-N-苯基甲亚胺（15）：浅
1-(5-氟-1H-吲哚-3-基)-N-苯基甲亚胺（11）：浅
黄色固体，收率 81.6%；熔点：188~190 ℃；HPLC
黄色固体，收率 78.2%；熔点：154~157 ℃；HPLC 纯度 > 95%。IR (ν/cm ): 3236 (N—H), 1672 (C==N),
–1
–1
纯度 > 95%。IR (ν/cm ): 3233 (N—H), 1679 (C==N), 1539 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.63
1
1
1538 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.51 (s, 1H), 8.87 (s, 1H), 7.58 (t, J = 2.0 Hz, 1H), 7.52 (d,
(s, 1H), 8.93 (s, 1H), 7.59 (d, J = 7.6 Hz, 2H), 7.50 (t, J = 7.2 Hz, 2H), 7.45 (d, J = 7.6 Hz, 2H), 7.40~7.37
J = 2.8 Hz, 1H), 7.48 (s, 1H), 7.38~7.35 (m, 3H), 7.32 (m, 1H), 7.35 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 6.92 (d,
13
(d, J = 7.6 Hz, 1H), 6.84 (d, J = 7.6 Hz, 1H); CNMR J = 7.2 Hz, 1H); CNMR (100 MHz, 丙酮-d 6 ), δ:
13
1
(100 MHz, 丙酮-d 6 ), δ: 160.1, 158.1 (d, J C — F = 235.3 157.2, 143.5, 134.7, 130.5, 129.6, 128.2, 126.1, 125.8,
Hz), 145.2, 132.8, 131.2, 130.7, 127.9, 124.7, 119.8 (d, 125.6, 124.3, 120.9, 112.4, 109.8; HRMS (ESI), m/Z:
2
2 J C — F = 18.0 Hz), 112.3 (d, J C — F = 27.2 Hz), 111.9 (d, [C 15 H 11 ClN 2 +H] 理论值 255.7250，实测值 255.7247。
+
3
J C — F = 10.1 Hz), 108.3, 106.5; HRMS (ESI), m/Z: 1-(6-氯-1H-吲哚-3-基)-N-苯基甲亚胺（16）：浅
+
[C 15 H 11 FN 2 +H] 理论值 239.2734，实测值 239.2737。 黄色固体，收率 83.1%；熔点：197~199 ℃；HPLC
–1
1-(6-氟-1H-吲哚-3-基)-N-苯基甲亚胺（12）：浅 纯度 > 95%。IR (ν/cm ): 3234 (N—H), 1675 (C==N),
1
黄色固体，收率 80.7%；熔点：166~168 ℃；HPLC 1537 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.59
–1
纯度 > 95%。IR (ν/cm ): 3231 (N—H), 1672 (C==N), (s, 1H), 8.87 (s, 1H), 7.66 (d, J = 8.4 Hz, 1H), 7.59 (d,
1
1532 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.54 J = 8.0 Hz, 2H), 7.56 (t, J = 2.0 Hz, 1H), 7.51~7.42 (m,
13
3H), 7.39 (d, J = 8.0 Hz, 1H), 7.28 (s, 1H); CNMR
(s, 1H), 8.90 (s, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.58 (d,
J = 8.4 Hz, 2H), 7.55 (t, J = 2.4 Hz, 1H), 7.48~7.35 (m, (100 MHz, 丙酮-d 6 ), δ: 157.2, 143.3, 136.7, 130.6,
13
3H), 7.31 (d, J = 8.0 Hz, 1H), 7.08 (s, 1H); CNMR 129.5, 128.4, 127.5, 125.3, 124.5, 123.1, 121.4, 114.8,
+
1
(100 MHz, 丙酮-d 6 ), δ: 160.1, 159.4 (d, J C — F = 108.2; HRMS (ESI), m/Z: [C 15 H 11 ClN 2 +H] 理论值
3
237.4 Hz), 145.2, 137.4 (d, J C — F = 10.1 Hz), 131.6, 255.7250，实测值 255.7252。
130.9, 129.7, 125.1, 123.1, 122.5, 109.8, 109.2 (d, 1-(7-氯-1H-吲哚-3-基)-N-苯基甲亚胺（17）：浅
2 2
J C — F = 24.2 Hz), 98.3 (d, J C — F = 25.4 Hz); HRMS 黄色固体，收率 80.9%；熔点：184~187 ℃；HPLC
–1
+
(ESI), m/Z: [C 15 H 11 FN 2 +H] 理论值 239.2734，实测值 纯度 > 95%。IR (ν/cm ): 3237 (N—H), 1672 (C==N),
1
239.2732。 1534 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.58
1-(7-氟-1H-吲哚-3-基)-N-苯基甲亚胺（13）：浅 (s, 1H), 8.90 (s, 1H), 7.62 (d, J = 8.4 Hz, 1H), 7.59 (d,
J = 7.6 Hz, 2H), 7.53 (t, J = 2.0 Hz, 1H), 7.46 (d, J =
黄色固体，收率 73.3%；熔点：173~176 ℃；HPLC 7.6 Hz, 2H), 7.39~7.35 (m, 1H), 7.31 (t, J = 8.0 Hz,
–1
纯度 > 95%。IR (ν/cm ): 3237 (N—H), 1676 (C==N), 1H), 7.29 (d, J = 7.6 Hz, 1H); CNMR (100 MHz, 丙
13
1
1537 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.51 酮-d 6 ), δ: 157.6, 143.2, 136.4, 130.3, 129.7, 128.8,
(s, 1H), 8.93 (s, 1H), 7.64 (d, J = 8.0 Hz, 1H), 7.58 (d, 127.5, 126.2, 121.7, 121.3, 120.4, 118.5, 109.6; HRMS
J = 7.6 Hz, 2H), 7.53 (t, J = 2.8 Hz, 1H), 7.51~7.41 (m, (ESI), m/Z: [C 15H 11ClN 2+H] 理论值 255.7250，实测值
+
3H), 7.33 (t, J = 8.0 Hz, 1H), 7.21 (d, J = 7.2 Hz, 1H);
13 1 255.7253。
CNMR (100 MHz, 丙酮-d 6), δ: 160.3, 149.2 (d, J C — F
2
= 242.9 Hz), 145.5, 132.8 (d, J C — F = 15.5 Hz), 131.4, 1-(4-溴-1H-吲哚-3-基)-N-苯基甲亚胺（18）：浅
3
130.2, 128.8, 125.9, 125.2, 122.6 (d, J C — F = 13.2 Hz), 黄色固体，收率 75.4%；熔点：204~206 ℃；HPLC
–1
2
116.1, 108.7 (d, J C — F = 15.7 Hz), 103.7; HRMS (ESI), 纯度 > 95%。IR (ν/cm ): 3239 (N—H), 1678 (C==N),
1
+
m/Z: [C 15 H 11 FN 2 +H] 理论值 239.2734，实测值 239.2733。 1532 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.52
(s, 1H), 8.94 (s, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.57 (d,
1-(4-氯-1H-吲哚-3-基)-N-苯基甲亚胺（14）：浅
J = 7.2 Hz, 2H), 7.49 (t, J = 2.0 Hz, 1H), 7.45 (d, J =
黄色固体，收率 78.4%；熔点：192~195 ℃；HPLC 8.0 Hz, 2H), 7.37 (t, J = 8.0 Hz, 1H), 7.37~7.32 (m,
13
–1
纯度 > 95%。IR (ν/cm ): 3244 (N—H), 1678 (C==N), 1H), 7.11 (d, J = 7.2 Hz, 1H); CNMR (100 MHz, 丙
1
1536 (C==C); HNMR (400 MHz, 丙酮-d 6 ), δ: 11.61 酮-d 6 ), δ: 160.1, 144.2, 136.5, 130.8, 130.1, 127.8,