刘雪松，于顺明
3. 实验部分
3.1. 仪器和试剂
所有化合物的1H NMR和13C NMR是用Bruker Avance IIIHD(500 MHz)型号的核磁测定的。核磁实验所用溶剂为CDCl3或DMSO-d6。1H化学位移以TMS(δ 0.00)或者CDCl3(δ 7.26)为参考，13C化学位移以CDCl3(δ 77.16)为参考，所有的化学位移单位为ppm。谱图中峰的多重性如下(s为单峰，d为双峰t为三重峰，m为多重峰或者未解析的峰，brs为宽峰，耦合常数以Hz为单位)。所有化合物的高分辨质谱都是用Agilent Techologies 6230 TOF LC/MS型高分辨质谱仪测定的。
3.2. PS-FeCl3催化剂的制备
PS-FeCl3催化剂按照文献方法制备[13]：向装有回流冷凝管、温度计以及电动搅拌器的三口瓶中加入聚苯乙烯粉末及甲苯，在搅拌器加入FeCl3，回流反应。反应过程中，有沉淀生成。冷却后，过滤，固体经水、丙酮及甲基叔丁基醚洗涤，固体经真空干燥，保存待用。PS-FeCl3用等离子体发射光谱法(ICP)测定，FeCl3的负载量约为1.6 mmol/g。
3.3. PS-FeCl3催化的三组分“一锅法”合成螺环苯并吡喃[2,3-b]吲哚类化合物
向10 mL反应管中，加入靛红1 (1.0 mmol)、苯酚2 (1.0 mmol)和2-卤代吲哚3 (1.2 mmol)以及PS-FeCl3(2.0 g)以及无水二氯甲烷(10 mL)，所得混合物置于室温下，振荡反应约24小时，并用薄层色谱(TLC)跟踪反应进程至2-卤代吲哚3完全转化。反应混合物经硅藻土过滤，滤饼用二氯甲烷洗涤，合并有机滤液后浓缩，粗产品经硅胶柱层析快速纯化得相应的目标化合物4a-o。
3.4. 实验数据
化合物4a：m.p. > 300?C.1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 7.39 (ddd, J = 8.5, 5.4, 3.6 Hz, 1H), 7.09 (d, J = 7.8 Hz, 1H), 7.02 (d, J = 3.7 Hz, 3H), 6.96 (s, 1H), 6.90 (t, J = 8.6 Hz, 2H), 6.79 (t, J = 7.5 Hz, 1H), 6.47 (d, J = 2.2 Hz, 1H), 6.36 (d, J = 7.8 Hz, 1H), 3.44 (s, 3H), 2.18 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 178.9, 149.0, 146.5, 143.6, 134.9, 133.8, 131.0, 129.5, 128.7, 128.0, 125.5, 124.3, 123.7, 121.1, 120.6, 120.1, 117.6, 116.6, 110.8, 108.1, 86.3, 51.1, 26.8, 20.7. HRMS (ESI-TOF) m/z: calcd for C24H19N2O2 [M+H]+ 367.1447, found 367.1445.
化合物4b：m.p. 288?C - 290?C. 1H NMR (400 MHz, CDCl3) δ9.47 (s, 1H), 7.46 - 7.34 (m, 6H), 7.31 (dt, J = 6.3, 3.1 Hz, 1H), 7.14 (d, J = 7.8 Hz, 1H), 7.07 (d, J = 7.2 Hz, 1H), 7.03 (t, J = 7.3 Hz, 1H), 6.92 - 6.88 (m, 1H), 6.84 (dd, J = 11.2, 5.1 Hz, 3H), 6.78 (d, J = 8.0 Hz, 1H), 6.41 (d, J = 7.1 Hz, 1H), 3.51 (s, 3H). 13C NMR (100 MHz, CDCl3) δ179.4, 150.5, 146.5, 143.5, 140.2, 137.3, 134.9, 131.3, 128.8, 128.7 (2C), 127.5, 127.1, 127.0 (2C), 126.4, 125.6, 124.1, 124.0, 121.6, 120.6, 119.8, 118.6, 116.4, 111.1, 108.2, 85.8, 51.4, 26.9. HRMS (ESI-TOF) m/z: calcd for C29H21N2O2 [M+H]+ 429.1603, found 429.1602.
化合物4c：m.p. 294?C - 295?C. 1H NMR (400 MHz, CDCl3) δ8.92 (s, 1H), 7.40 (ddd, J = 8.4, 6.2, 2.8 Hz, 1H), 7.11 (d, J = 7.8 Hz, 1H), 7.04 (q, J = 4.1, 3.4 Hz, 2H), 6.96 - 6.86 (m, 3H), 6.85 - 6.76 (m, 2H), 6.38 (d, J = 7.8 Hz, 1H), 6.23 (d, J = 2.9 Hz, 1H), 3.68 (s, 3H), 3.46 (s, 3H). 13C NMR (100 MHz, CDCl3) δ178.9, 155.9, 146.9, 145.3, 143.5, 134.5, 131.2, 128.8, 125.5, 124.3, 123.8, 122.2, 120.5, 120.0, 118.7, 116.5, 113.9, 112.8, 110.9, 108.1, 85.6, 55.6, 51.4, 26.8. HRMS (ESI-TOF) m/z: Calcd for C24H19N2O3 [M+H]+ 383.1396, found 383.1393.
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1
化合物4d：H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 7.43 - 7.38 (m, 1H), 7.09 (d, J = 7.8 Hz, 1H), 7.07 -
7.99 (m, 3H), 6.99-6.92 (m, 2H), 6.83 - 6.72 (t,J = 6.0 Hz, 1H), 6.42-6.31 (m, 2H), 3.42 (s, 3H). 13C NMR (101 MHz, CDCl3) δ166.9, 154.4, 152.9, 145.5, 143.8. 138.0, 136.5, 134.9, 129.4, 127.4, 126.9, 126.4, 124.8, 121.7, 119.8, 118.8, 117.5, 115.9, 114.7, 111.6, 109.8, 59.9, 36.4. HRMS (ESI-TOF) m/z: calcd for C26H16N2O3 [M+H]+369.1239, found 369.1240.
化合物4e：m.p. 290?C - 291?C.1H NMR (400 MHz, CDCl3) δ9.61 (s, 1H), 7.47-7.35 (m, 1H), 7.13 (d, J = 7.9 Hz, 1H), 7.02 (ddd, J = 13.6, 7.4, 4.8 Hz, 3H), 6.88 - 6.75 (m, 2H), 6.76 - 6.69 (m, 1H), 6.67 (d, J = 9.0 Hz, 1H), 6.52 (d, J = 2.9 Hz, 1H), 6.42 - 6.30 (m, 1H), 3.49 (s, 3H). 13C NMR (100 MHz, CDCl3) δ179.0, 149.3, 146.3, 144.9 (q, JC-F = 1.8 Hz), 143.2, 134.2, 131.3, 129.2, 125.5, 124.2, 123.8, 122.7, 121.3, 120.8, 120.4, 120.3 (q, JC-F = 85.2 Hz), 120.0, 119.4, 116.5, 111.1, 108.5, 85.2, 51.4, 27.0. HRMS (ESI-TOF) m/z: calcd for C24H16F3N2O3 [M+H]+ 437.1113, found 437.1106.
化合物4f：m.p. 276?C - 277?C. 1H NMR (400 MHz, DMSO- d6) δ11.67 (s, 1H), 7.39 (t, J = 7.6 Hz, 1H), 7.25 (d, J = 8.0 Hz, 2H), 7.07 - 6.86 (m, 4H), 6.75 (t, J = 7.5 Hz, 1H), 6.30 (d, J = 7.8 Hz, 1H), 6.11 (s, 1H), 6.02 (d, J = 5.7 Hz, 2H), 3.30 (s, 3H). 13C NMR (100 MHz, DMSO-d6) δ177.2, 147.5, 146.1, 145.5, 144.2, 143.4, 134.3, 130.9, 128.8, 124.4, 123.5, 123.0, 120.2, 119.5, 116.1, 113.3, 110.9, 108.9, 105.8, 101.9, 98.7, 85.6, 50.4, 26.4. HRMS (ESI-TOF) m/z: calcd for C24H16N2NaO4Na [M+Na]+ 419.1008, found 419.1003.
化合物4g：m.p. > 300?C. 1H NMR (400 MHz, CDCl3) δ8.81 (s, 1H), 7.46-7.31 (m, 1H), 7.09 (d, J = 8.0 Hz, 1H), 7.01 (q, J = 5.0, 4.6 Hz, 2H), 6.87 (d, J = 6.6 Hz, 2H), 6.83 - 6.72 (m, 2H), 6.50 (s, 1H), 6.37 (d, J = 7.8 Hz, 1H), 3.44 (s, 3H), 2.85 (q, J = 6.9 Hz, 2H), 2.73 (qt, J = 15.3, 6.4 Hz, 2H), 2.03 (ddt, J = 13.7, 10.0, 6.1 Hz, 2H).
13
C NMR (100 MHz, CDCl3) δ179.65, 149.75, 146.86, 145.31, 143.54, 140.20, 135.40, 131.25, 128.59, 125.53,
124.40, 123.79, 122.77, 120.13, 119.79, 118.84, 116.41, 113.85, 111.03, 108.07, 85.86, 51.40, 32.77, 32.13, 26.88, 25.86. HRMS (ESI-TOF) m/z: calcd for C26H21N2O2 [M+H]+ 393.1603, found 393.1596.
化合物4h：m.p. 282?C - 283?C. 1H NMR (400 MHz, CDCl3) δ9.20 (s, 1H), 7.37 (ddd, J = 7.8, 5.5, 3.5 Hz, 1H), 7.09 (d, J = 7.8 Hz, 1H), 7.04 - 6.95 (m, 2H), 6.85 - 6.79 (m, 1H), 6.76 (ddd, J = 9.3, 7.3, 2.3 Hz, 2H), 6.48 (s, 1H), 6.34 (d, J = 6.8 Hz, 2H), 3.46 (s, 3H), 2.68 (q, J = 5.4 Hz, 2H), 2.56 (qd, J = 16.4, 8.1 Hz, 2H), 1.81 - 1.64 (m, 4H).13C NMR (100 MHz, CDCl3) δ179.7, 148.7, 146.8, 143.6, 138.0, 135.3, 133.1, 131.2, 128.6, 127.6, 125.5, 124.4, 123.8, 120.1, 119.7, 118.5, 117.8, 116.3, 111.1, 108.1, 85.9, 51.1, 29.2, 28.7, 26.9, 23.2, 22.9. HRMS (ESI-TOF) m/z: calcd for C27H23N2O2 [M+H]+ 407.1760, found 407.1755.
化合物4i：m.p. > 300?C. 1H NMR (400 MHz, CDCl3) δ9.18 (s, 1H), 7.46 - 7.35 (m, 1H), 7.11 (d, J = 7.8 Hz, 1H), 7.06 - 6.98 (m, 2H), 6.90 (ddd, J = 8.9, 7.5, 3.0 Hz, 1H), 6.85 (dd, J = 6.9, 1.5 Hz, 1H), 6.84 - 6.79 (m, 2H), 6.79 - 6.74 (m, 1H), 6.39 (dd, J = 9.0, 3.1 Hz, 1H), 6.36 (d, J = 7.4 Hz, 1H), 3.46 (s, 3H). 13C NMR (100 MHz, CDCl3) δ178.7, 158.8 (d, JC-F= 241.2 Hz), 147.2 (d, JC-F = 1.1 Hz), 146.5, 143.4, 134.2, 131.3, 129.1, 125.5, 124.0, 122.8 (d, JC-F = 3.6 Hz), 120.8, 120.1, 119.4, 119.3, 116.6, 115.8 (d, JC-F = 11.8 Hz), 113.5 (d, JC-F = 11.9 Hz), 111.0, 108.4, 85.3, 51.5, 26.9. HRMS (ESI-TOF) m/z: calcd for C23H16FN2O2 [M+H]+ 371.1196, found 371.1186.
化合物4j：m.p. 298?C - 300?C. 1H NMR (400 MHz, DMSO- d6) δ 11.73 (s, 1H), 7.36 (d, J = 6.3 Hz, 2H), 7.27 (d, J = 8.0 Hz, 1H), 7.17 (q, J = 8.1 Hz, 2H), 7.12 - 7.03 (m, 1H), 6.97 (t, J = 7.7 Hz, 1H), 6.77 (d, J = 10.7 Hz, 2H), 6.69 (d, J = 7.8 Hz, 1H), 6.35 (d, J = 7.8 Hz, 1H), 3.30 (s, 3H), 2.13 (s, 3H). 13C NMR (100 MHz,DMSO-d6) δ 177.0, 150.4, 145.8, 140.9, 134.7, 132.1, 130.8, 128.9, 128.8, 128.2, 124.9, 124.5, 123.6,
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121.8, 120.2, 119.5, 117.3, 116.1, 110.9, 108.5, 85.9, 50.2, 26.3, 20.3. HRMS (ESI-TOF) m/z: calcd for C24H19N2O2 [M+H]+ 367.1447, found 367.1446.
化合物4k：m.p. > 300?C. 1H NMR (400 MHz, DMSO-d6) δ11.80 (s, 1H), 7.59 (dd, J = 8.3, 2.1 Hz, 1H), 7.46 - 7.33 (m, 2H), 7.28 (t, J = 8.3 Hz, 2H), 7.15 - 7.05 (m, 2H), 7.00 (t, J = 7.6 Hz, 1H), 6.81 (t, J = 7.5 Hz, 1H), 6.74 (d, J = 7.8 Hz, 1H), 6.37 (d, J = 7.8 Hz, 1H), 3.32 (s, 3H). 13C NMR (100 MHz,DMSO-d6) δ176.7, 150.4, 145.9, 142.7, 136.8, 131.6, 130.8, 129.1, 128.1, 127.1, 124.6, 123.4, 120.9, 120.3, 119.7, 117.5, 115.9, 114.8, 111.1, 111.0, 85.1, 50.3, 26.5. HRMS (ESI-TOF) m/z: calcd for C23H16BrN2O2 [M+H]+ 431.0395, found 431.0389.
化合物4l：m.p. > 300?C. 1H NMR (400 MHz, DMSO-d6) δ11.55 (s, 1H), 7.40 (t, J = 7.7 Hz, 1H), 7.28 (d, J = 7.9 Hz, 1H), 7.23 (d, J = 8.5 Hz, 1H), 7.20 - 7.07 (m, 2H), 6.98 (t, J = 7.5 Hz, 1H), 6.90 (d, J = 7.4 Hz, 1H), 6.78 (d, J = 8.2 Hz, 1H), 6.46 (s, 1H), 6.07 (s, 1H), 3.33 (s, 3H), 2.14 (s, 3H), 2.11 (s, 3H). 13C NMR (100 MHz,DMSO-d6) δ177.2, 148.5, 146.1, 143.3, 134.6, 133.5, 129.6, 129.0, 128.7, 127.9, 127.8, 124.4, 123.8, 123.1, 121.4, 121.3, 117.1, 116.0, 110.7, 108.7, 85.5, 50.2, 26.4, 21.2, 20.1. HRMS (ESI-TOF) m/z: calcd for C25H21N2O2 [M+H]+ 381.1603, found 381.1596.
化合物4m：m.p. > 300?C. 1H NMR (400 MHz, CDCl3) δ 9.71 (s, 1H), 7.44 (td, J = 7.7, 1.3 Hz, 1H), 7.30 (dd, J = 8.8, 2.4 Hz, 1H), 7.15 (d, J = 7.8 Hz, 1H), 7.07 (t, J = 7.5 Hz, 1H), 7.02 - 6.96 (m, 1H), 6.79 (d, J = 2.4 Hz, 1H), 6.63 (d, J = 8.8 Hz, 1H), 6.60 - 6.46 (m, 2H), 5.97 (dd, J = 9.5, 2.4 Hz, 1H), 3.51 (s, 3H). 13C NMR (100 MHz,CDCl3) δ 179.0, 157.9 (d, JC-F = 116.3 Hz), 150.0, 147.2, 143.1, 133.8, 131.8, 130.5, 129.4, 127.6, 125.5, 124.4, 124.2 (d, JC-F = 5.2 Hz), 123.2, 119.9, 116.5, 111.8 (d, JC-F = 4.8 Hz), 108.7, 108.3 (d, JC-F = 12.8 Hz), 102.0 (d, JC-F = 12.4 Hz), 85.7 (d, JC-F = 2.1 Hz), 51.1, 27.1. HRMS (ESI-TOF) m/z: calcd for C23H14BrFN2O2 [M+H]+ 449.0301, found 449.0297.
化合物4n：m.p. > 300?C. 1H NMR (400 MHz, DMSO- d6) δ11.94 (s, 1H), 7.50 - 7.38 (m, 2H), 7.34 - 7.20 (m, 3H), 7.07 - 6.94 (m, 2H), 6.81 (td, J = 9.3, 2.6 Hz, 1H), 6.54 (dd, J = 9.0, 3.1 Hz, 1H), 5.93 (dd, J = 9.6, 2.6 Hz, 1H), 3.32 (s, 3H). 13C NMR (100 MHz, DMSO- d6) δ176.4, 158.3 (d, JC-F = 239.6 Hz), 156.9 (d, JC-F = 231.1 Hz),147.3, 146.8 (d, JC-F = 1.1 Hz), 143.4, 133.3, 129.2, 127.4, 124.5, 123.7 (d, JC-F = 3.7 Hz), 123.2, 123.1 (d, JC-F = 3.7 Hz), 119.2 (d, JC-F = 4.2 Hz,), 116.3 (d, JC-F = 12.8 Hz), 113.5 (d, JC-F = 12.8 Hz), 112.2 (d, JC-F = 4.8 Hz), 109.2, 107.9 (d, JC-F = 12.6 Hz), 101.3 (d, JC-F = 12.1 Hz), 85.8 (d, JC-F = 2.1 Hz), 50.3, 26.4. HRMS (ESI-TOF) m/z: calcd for C23H15F2N2O2 [M+H]+ 389.1102, found 389.1093.
化合物4o：m.p. 289?C - 290?C. 1H NMR (400 MHz, DMSO- d6) δ11.78 (s, 1H), 7.44 (d, J = 6.5 Hz, 2H), 7.41 - 7.37 (m, 2H), 7.35 (d, J = 7.5 Hz, 2H), 7.34 - 7.29 (m, 2H), 7.25 (dd, J = 17.5, 8.0 Hz, 2H), 7.09 (ddd, J = 8.3, 5.9, 2.7 Hz, 1H), 6.96 (d, J = 4.5 Hz, 3H), 6.67 (t, J = 7.9 Hz, 2H), 6.19 (d, J = 7.8 Hz, 1H), 5.08 (d, J = 15.4 Hz, 1H), 5.00 (d, J = 15.4 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ177.4, 150.5, 146.0, 142.4, 136.3, 134.4, 130.8, 129.0, 128.7, 128.5 (2C), 127.8, 127.7 (2C), 127.6, 124.7, 124.6, 123.5, 123.2, 121.7, 120.3, 119.3, 117.5, 116.4, 111.0, 109.4, 85.7, 50.2, 43.3. HRMS (ESI-TOF) m/z: calcd for C29H21N2O2 [M+H]+ 429.1603, found 429.1598.
化合物4p：m.p. > 300?C. 1H NMR (400 MHz, DMSO-d6) δ11.71 (s, 1H), 10.74 (s, 1H), 7.41 - 7.32 (m, 2H), 7.32 - 7.24 (m, 2H), 7.10 (t, J = 8.1 Hz, 2H), 7.01 - 6.94 (m, 1H), 6.94 - 6.86 (m, 2H), 6.79 (t, J = 7.5 Hz, 1H), 6.74 (dd, J = 7.8, 1.5 Hz, 1H), 6.42 (d, J = 7.8 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ178.8, 150.5, 145.8, 141.9, 135.2, 130.8, 128.8, 128.7, 128.0, 124.8, 124.5, 123.78, 122.4, 121.9, 120.1, 119.4, 117.3, 116.1, 110.9, 109.7, 85.9, 50.6. HRMS (ESI-TOF) m/z: calcd for C22H15N2O2 [M+H]+ 339.1134, found 339.1126.
DOI: 10.12677/jocr.2020.82002
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4. 总结
在本文中，我们以靛红、苯酚以及2-卤吲哚类化合物为起始物料，在聚苯乙烯负载型氯化铁催化剂(PS-FeCl3)催化下，快速简便的合成了一系列螺环苯并吡喃[2,3-b]吲哚类化合物。在该反应过程中，我们实现了多组分“一锅法”合成策略；而且，利用PS-FeCl3做催化剂，反应条件温和，操作简便，催化剂性能稳定。该反应具有底物适用范围广、反应条件温和、操作简单等优点。最后，我们还对此反应提出了一个可能的反应机理，为构建复杂螺环吲哚类化合物供了重要的理论参考。
致 谢
感谢中国科学院上海有机化学研究所冷雪冰教授在晶体结构分析上提供的帮助。
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DOI: 10.12677/jocr.2020.82002
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有机化学研究
固载化FeCl3催化合成螺环苯并吡喃2,3-b吲哚类衍生物 - 图文
