CN111560006A - 一种制备多取代噻吩的方法 - Google Patents

一种制备多取代噻吩的方法 Download PDF

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CN111560006A
CN111560006A CN201911243214.0A CN201911243214A CN111560006A CN 111560006 A CN111560006 A CN 111560006A CN 201911243214 A CN201911243214 A CN 201911243214A CN 111560006 A CN111560006 A CN 111560006A
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程斌
李运通
翟宏斌
张昕平
李慧
胡汉巍
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Lanzhou University
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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Abstract

本申请属于化学合成技术领域，具体涉及一种制备多取代噻吩的方法，操作简单，绿色环保，产率高，适合大规模制备。该方法实现了含硫内鎓盐和缺电子的炔作为起始原料，在二氯乙烷中，无需其它催化剂或金属试剂，只需要加热的条件下制备四取代和三取代噻吩，特别是氟代的噻吩。

Description

一种制备多取代噻吩的方法
技术领域
本申请属于化学合成技术领域，具体涉及一种制备多取代噻吩的方法。
背景技术
众所周知，噻吩作为一类含硫五元杂环，广泛分布于天然产物，药物分子和功能材料中，并常被用作有机化学和材料化学中重要的合成中间体。因此，有机化学家一直致力于发展高效的方法来构建这种独特的杂环。然而，合成多取代噻吩的方法有限，其中许多涉及金属催化剂，恶臭原料或苛刻的反应条件。此外，对于药物和材料化学，产品中的金属污染始终是一个难题。此外，用相同的方案将多种氟基团(例如SCF3，CF3)引入到噻吩中是特别吸引人的，这种方法文献很少见。因此，开发一种通用的方法来获得多取代噻吩就变得非常有必要。
发明内容
本申请主要提供一种操作简单、绿色环保、适合大规模制备多取代噻吩的方法。该方法实现了含硫内鎓盐和缺电子的炔作为起始原料，在二氯乙烷中，无需其它催化剂或金属试剂，只需要加热的条件下制备四取代和三取代噻吩，特别是氟代的噻吩。
制备方法：将通式原料含硫内鎓盐A和缺电子的炔B在二氯乙烷中混合，在85度加热。待反应物B完全消失，将反应物浓缩旋干、柱色谱分离得到目标分子多取代噻吩。
Figure BDA0002306833040000011
其中
X选自H、Me、OMe或者NMe2，优选OMe；
EWG1选自：CO2Me,CO2Et,COPh,CF3
EWG2选自：CO2Me,CO2Et,COPh
EWG3选自：COR1,R1＝C6H5,(CH2)10CH3,OEt,4-BrC6H4,2-Naphthnyl,2-Thienyl,2-Furyl,O-2-Naphthnyl
Y选自:CO2Me,CONMePh,CH(OEt)2,COPh,CO(CH2)10CH3,CO2Et,CF3,CF2-4-BrC6H4,CHFMe,SCF3,H
进一步地，上述方法中，反应温度为85℃。
进一步地，上述方法中，反应物A与反应物B的摩尔比为1.5:1。
进一步地，上述方法中，溶剂二氯乙烷(DCE)的浓度优选0.1M。
附图说明
图1是本发明实施例所得到的产物Ⅰ-1的核磁共振氢谱图；
图2是本发明实施例所得到的产物Ⅰ-1的核磁共振碳谱图。
具体实施方式
本发明以下结合具体实施例进行解说。在以下所有实施例中，核磁谱检测通过Varian 300,Bruker 400,JEOL 400and Varian 600MHz仪器在CDCl3、(CD3)2CO中获得。δ值为内标相对值(CDCl3定标δ7.26 1H NMR和77.00 13C NMR)。高分辨质谱(HRMS)通过4Gquadrupole time-of-flight(QTof)质谱仪器得到。
实施例1
实施例1的反应式，具体使用的原料化合物A-1和B-1以及产物Ⅰ-1结构如下
Figure BDA0002306833040000031
具体实验步骤是：将127mg(0.45mmol，1.5当量)的化合物A-1和56mg(0.3mmol,1.0当量)的化合物B-1溶于3mL的二氯乙烷中于85℃反应。反应监测B-1完全消失，反应结束，将反应混合物在水泵减压下旋转蒸发除去溶剂二氯乙烷。残留物以200-300目硅胶柱层析得到Ⅰ-1所示化合物，其产物经过核磁(氢谱、碳谱)、高分辨质谱鉴定。
产物Ⅰ-1为黄色油，产率为81％.1H NMR(400MHz,CDCl3)δ7.79(d,J＝7.3Hz,2H),7.60(t,J＝7.4Hz,1H),7.46(t,J＝7.7Hz,2H),3.95(s,3H),3.69(s,3H),3.68(s,3H)；13CNMR(100MHz,CDCl3)δ190.8,162.3 160.4,160.2,145.4 137.9,136.6,136.4,133.8,133.7,129.0,128.6,53.3,52.9,52.8；ESI-HRMS m/z calcd For C17H14O7S+H(M+H):363.0533,found 363.0547.
制备本发明的其它化合物(化合物Ⅰ-2至化合物Ⅰ-25)的实施例所用的方法与实施例1相同，反应条件如下：化合物A(0.45mmol，1.5当量)和化合物B(0.3mmol，1.0当量)溶于3mL的二氯乙烷中与85℃反应，反应监测B完全消失，反应结束，将反应混合物在水泵减压下旋转蒸发除去溶剂二氯乙烷。残留物以200-300目硅胶柱层析得到目标化合物，其产物经过核磁(氢谱、碳谱)、高分辨质谱鉴定。
所得各产物结构和数据表征如下：
Figure BDA0002306833040000041
产物Ⅰ-2为棕色油，产率为88％.1H NMR(300MHz,CDCl3)δ7.65(d,J＝7.3Hz,2H),7.56(t,J＝7.3Hz,1H),7.42(t,J＝7.6Hz,2H),7.34–7.21(m,3H),7.18–7.05(m,2H),3.81(s,3H),3.44(s,3H),3.28(s,3H)；13C NMR(75MHz,CDCl3)δ189.9,162.8,160.8,160.2,142.4,142.2,142.1,136.4,136.3,133.8,133.2,129.6,129.0,128.2,128.1,127.0,52.8,52.4,38.1；ESI-HRMS m/z calcd For C23H19NO6S+H(M+H):438.1006,found 438.1018.
产物Ⅰ-3为黄色油，产率为80％.1H NMR(300MHz,CDCl3)δ7.82–7.76(m,2H),7.62–7.54(m,1H),7.47–7.42(m,2H),5.68(s,1H),4.35(d,J＝7.1Hz,2H),4.00(q,J＝7.2Hz,2H),3.62–3.53(m,2H),3.50–3.39(m,2H),1.36(t,J＝7.1Hz,3H),1.11–1.03(m,9H)；13CNMR(75MHz,CDCl3)δ191.2,162.9,160.5,149.1,137.8,137.5,137.1,133.4,132.4,129.1,128.4,96.8,62.1,61.8,61.7,14.6,14.0,13.4；ESI-HRMS m/z calcd For C22H26O7S+Na(M+Na):457.1291,found 457.1309.
产物Ⅰ-4为棕色油，产率为99％.1H NMR(300MHz,CDCl3)δ7.56–7.45(m,6H),7.34–7.26(m,4H),4.42(q,J＝7.1Hz,2H),4.23(q,J＝7.2Hz,2H),1.39(t,J＝7.1Hz,3H),1.19(t,J＝7.1Hz,3H)；13C NMR(75MHz,CDCl3)δ190.2,186.9,162.6,159.8,144.2,143.5,138.5,137.0,136.8,136.1,133.4,133.3,128.9,128.7,128.4,128.3,62.4,62.1,13.9,13.5；ESI-HRMS m/z calcd For C24H20O6S+H(M+H):437.1053,found 437.1067.
产物Ⅰ-5为棕色油，产率为41％.1H NMR(400MHz,CDCl3)δ4.41–4.36(m,2H),4.36–4.30(m,2H),2.81(t,J＝7.3Hz,2H),2.75(t,J＝7.5Hz,2H),1.79–1.70(m,4H),1.40–1.26(m,38H),0.88(t,J＝6.8Hz,6H)；13C NMR(100MHz,CDCl3)δ201.4,192.1,162.5,160.1,146.8,140.0,136.6(2C),62.6,62.3,43.4,41.1,31.9(2C),29.6(3C),29.5,29.4(2C),29.3(2C),29.0(2C),24.2,23.3,22.7,14.1,14.0,13.8,(4C missing)；ESI-HRMS m/zcalcd For C34H56O6S+H(M+H):593.3870,found593.3894.
产物Ⅰ-6为无色油，产率为41％.1H NMR(400MHz,CDCl3)δ4.41–4.34(m,4H),3.92(s,6H),1.39–1.34(m,6H)；13C NMR(100MHz,CDCl3)δ162.9,162.3,160.4,159.8,137.0,136.9,136.6,135.6,62.5,62.3,53.1,53.0,14.0,13.9；ESI-HRMS m/z calcd ForC14H16O8S+H(M+H):345.0639,found 345.0651.
产物Ⅰ-7为黄色油，产率为68％.1H NMR(300MHz,CDCl3)δ7.84(d,J＝7.2Hz,2H),7.59–7.50(m,3H),7.48–7.34(m,6H),7.31–7.24(m,2H),7.18(t,J＝7.7Hz,2H),3.68(s,3H)；13C NMR(75MHz,CDCl3)δ191.1,190.2,187.0,160.4,146.6,145.6,144.0,137.2,136.9,136.7,134.3,133.6,133.4,133.2,129.0,128.9,128.8,128.4,128.2,52.8,(1Cmissing)；ESI-HRMS m/z calcd For C27H18O5S+H(M+H):455.0948,found 455.0963.
产物Ⅰ-8为红色油，产率为55％.1H NMR(400MHz,(CD3)2CO)δ7.81(d,J＝7.3Hz4H),7.73(d,J＝7.3Hz,4H),7.62(t,J＝7.5Hz,2H),7.52–7.47(m,2H),7.43(t,J＝7.8Hz,4H),7.32(t,J＝7.8Hz,4H)；13C NMR(75MHz,(CD3)2CO)δ191.2,187.7,146.4,145.0,138.3,138.1,134.5,134.2,130.0,129.7,129.5,129.2；ESI-HRMS m/z calcd For C32H20O4S+H(M+H):501.1155,found 501.1174.
产物Ⅰ-9为棕色油，产率为53％.1H NMR(400MHz,CDCl3)δ7.77(d,J＝7.3Hz,2H),7.69(d,J＝7.3Hz,2H),7.59–7.52(m,2H),7.47–7.39(m,4H),7.37–7.30(m,3H),7.27–7.24(m,2H),3.34(s,3H),3.11(s,3H)；13C NMR(100MHz,CDCl3)δ191.5,188.1,161.3,160.6,147.2,144.7,142.4,137.7,137.0,136.7,133.8,133.1,131.8,129.9,129.0,128.7,128.6,128.4,127.9,51.8,38.5,(1C missing)；ESI-HRMS m/z calcd For C28H21NO5S+H(M+H):484.1213,found 484.1229.
产物Ⅰ-10为黄色油，产率为44％.1H NMR(400MHz,CDCl3)δ4.40–4.27(m,6H),1.34–1.27(m,9H)；13C NMR(100MHz,CDCl3)δ163.3,159.6,159.3,140.9,138.6(q,J＝39.1Hz),132.1,132.0(q,J＝2.5Hz),120.6(q,J＝270.2Hz),62.6,62.4,62.3,14.0,13.9,13.7；19FNMR(376MHz,CDCl3)δ-55.3；ESI-HRMS m/z calcd For C14H15F3O6S+H(M+H):369.0614,found 369.0626.
产物Ⅰ-11为黄色油，产率为76％.1H NMR(400MHz,CDCl3)δ7.56(d,J＝8.5Hz,2H),7.40(d,J＝8.5Hz,2H),4.45–4.34(m,4H),4.09(q,J＝7.1Hz,2H),1.43–1.34(m,6H),1.10(t,J＝7.1Hz,3H)；13C NMR(100MHz,CDCl3)δ163.6,160.0,159.6,146.9(t,J＝33.0Hz),140.7,134.7(t,J＝27.1Hz),131.6,131.4,130.8(t,J＝3.8Hz),127.5(t,J＝5.0Hz),125.1,117.8(t,J＝240.8Hz),62.3,62.2,61.7,14.0,13.8,13.5；19F NMR(376MHz,CDCl3)δ-76.9；ESI-HRMS m/z calcd For C20H19BrF2O6S+H(M+H):505.0127,found 505.0146.
产物Ⅰ-12为无色油，产率为92％.1H NMR(400MHz,CDCl3)δ7.69–7.56(m,4H),5.90(dq,J＝50.4,6.4Hz,1H),4.37(q,J＝7.2Hz,2H),3.96–3.92(m,2H),1.70(dd,J＝23.6,6.4Hz,3H),1.37(t,J＝7.1Hz,3H),1.08(t,J＝7.1Hz,3H)；13C NMR(100MHz,CDCl3)δ189.8,162.7,160.1,152.2(d,J＝21.7Hz),137.2,136.5(d,J＝4.7Hz),135.8,132.3(d,J＝2.1Hz),131.9,130.7,129.0,85.5(d,J＝167.8Hz),62.2,62.0,23.6(d,J＝24.7Hz),14.0,13.5；19F NMR(376MHz,CDCl3)δ-157.6；19F NMR(376MHz,CDCl3)δ-157.6；ESI-HRMS m/zcalcd For C19H18BrFO5S+H(M+H):457.0115,found 457.0134.
产物Ⅰ-13为黄色油，产率为61％.1H NMR(400MHz,CDCl3)δ7.77–7.75(m,2H),7.64–7.60(m,1H),7.47(t,J＝7.7Hz,2H),4.40(q,J＝7.1Hz,2H),4.00(q,J＝7.1Hz,2H),1.38(t,J＝7.1Hz,3H),1.05(t,J＝7.2Hz,3H)；13C NMR(100MHz,CDCl3)δ189.4,161.9,159.4,148.7,139.5,137.3,136.4,134.0,129.5,128.7,127.7(q,J＝310.1Hz),126.8(q,J＝2.5Hz),62.6,62.2,14.0,13.4；19F NMR(376MHz,CDCl3)δ-42.8；19F NMR(376MHz,CDCl3)δ-42.8；ESI-HRMS m/z calcd For C18H15F3O5S2+H(M+H):433.0386,found 433.0399.
产物Ⅰ-14为白色固体，产率为85％.熔点：120-122℃.1H NMR(400MHz,CDCl3)δ7.78(d,J＝7.3Hz,2H),7.63–7.58(m,1H),7.47(t,J＝7.7Hz,2H),4.44(q,J＝7.2Hz,2H),3.73(s,3H),1.41(t,J＝7.1Hz,3H)；13C NMR(100MHz,CDCl3)δ190.1,159.9,158.9,145.0(q,J＝2.3Hz),139.7(q,J＝2.7Hz),136.2,134.0,133.6,131.8(q,J＝36.6Hz),128.9,128.8,120.2(q,J＝272.0Hz),63.0,53.0,13.9；19F NMR(376MHz,CDCl3)δ-55.0；ESI-HRMS m/zcalcd For C17H13F3O5S+H(M+H):387.0509,found 387.0527.
产物Ⅰ-15为黄色固体，产率为84％.熔点：140-141℃.1H NMR(400MHz,CDCl3)δ7.80–7.77(m,2H),7.58–7.56(m,1H),7.49–7.43(m,2H),7.42–7.38(m,3H),7.29–7.23(m,2H),4.30(q,J＝7.1Hz,2H),3.31(s,3H),1.30(t,J＝7.1Hz,3H)；13C NMR(100MHz,CDCl3)δ191.0,160.3,159.3,144.5,142.4,138.4,137.4(q,J＝3.0Hz),136.9,133.4,130.3(q,J＝36.4Hz),130.1,128.9,128.5,127.9,127.3,120.4(q,J＝272.0Hz),62.6,38.7,13.7；19FNMR(376MHz,CDCl3)δ-54.4；ESI-HRMS m/z calcd For C23H18F3NO4S+H(M+H):462.0981,found 462.0999.
产物Ⅰ-16为棕色油，产率为54％.1H NMR(400MHz,(CD3)2CO)δ7.86–7.84(m,2H),7.71–7.67(m,1H),7.56(t,J＝7.7Hz,2H),5.62(s,1H),4.41(q,J＝7.1Hz,2H),3.58–3.43(m,4H),1.38(t,J＝7.1Hz,3H),0.99(t,J＝7.0Hz,6H)；13C NMR(100MHz,(CD3)2CO)δ191.2,160.0,148.2,138.4(q,J＝2.3Hz),137.8,135.5(q,J＝3.0Hz),134.8,131.8(q,J＝35.7Hz),130.0,129.7,121.9(q,J＝270.9Hz),97.6,63.1,62.8,14.9,14.3；19F NMR(376MHz,Acetone)δ-54.7；ESI-HRMS m/z calcd For C20H21F3O5S+Na(M+Na):453.0954,found 453.0966.
产物Ⅰ-17为黄色油，产率为82％.1H NMR(400MHz,CDCl3)δ7.75–7.72(m,4H),7.60–7.53(m,2H),7.44–7.39(m,4H),4.44(q,J＝7.1Hz,2H),1.40(t,J＝7.1Hz,3H)；13C NMR(100MHz,CDCl3)δ190.4,186.0,159.1,145.0(q,J＝2.2Hz),141.0,139.3(q,J＝2.8Hz),136.6,136.5,133.7(2C),132.1(q,J＝36.5Hz),129.2,128.8,128.6,121.0(q,J＝272.1Hz),63.1,13.8,(1C missing)；19F NMR(376MHz,CDCl3)δ-54.7；ESI-HRMS m/z calcdFor C22H15F3O4S+H(M+H):433.0716,found433.0729.
产物Ⅰ-18为黄色油，产率为81％.1H NMR(300MHz,CDCl3)δ7.93(s,1H),7.84–7.77(m,2H),7.64–7.57(m,1H),7.52–7.45(m,2H),3.93(s,3H),3.91(s,3H)；13C NMR(75MHz,CDCl3)δ188.3,165.0,160.5,139.8,139.7,137.7,137.0,133.0,132.3,129.3,128.5,53.0,52.8；ESI-HRMS m/z calcd For C15H12O5S+Na(M+Na):327.0298,found 327.0308.
产物Ⅰ-19为橘红色固体，产率为74％.熔点：130-131℃.1H NMR(400MHz,CDCl3)δ8.13–8.10(m,1H),7.91(d,J＝8.2Hz,1H),7.82–7.79(m,1H),7.68(s,1H),7.57(dd,J＝7.1,1.3Hz,1H),7.45–7.43(m,2H),7.40(t,J＝8.3,,1H),3.84(s,3H),3.82(s,3H)；13C NMR(100MHz,CDCl3)δ189.6,165.2,160.6,141.5,139.5,139.2,135.0,133.6,132.2(2C),130.4,128.3,128.1,127.6,126.7,125.3,124.1,53.1,52.9；ESI-HRMS m/z calcd ForC19H14O5S+H(M+H):355.0635,found 355.0648.
产物Ⅰ-20为黄色固体，产率为69％.熔点：104-105℃.1H NMR(400MHz,CDCl3)δ8.59(s,1H),7.69(dd,J＝1.7,0.8Hz,1H),7.37(dd,J＝3.7,0.8Hz,1H),6.62(dd,J＝3.7,1.7Hz,1H),4.00(s,3H),3.91(s,3H)；13C NMR(75MHz,CDCl3)δ173.4,165.3,160.6,152.2,146.9,140.1,138.2,137.8,131.5,120.0,112.7,53.0,52.8；ESI-HRMS m/z calcd ForC13H10O6S+Na(M+Na):317.0090,found 317.0103.
产物Ⅰ-21为棕色油，产率为71％.1H NMR(400MHz,CDCl3)δ8.04(s,1H),7.68–7.64(m,2H),7.09(dd,J＝5.2,4.0Hz,1H),3.87(s,3H),3.83(s,3H)；13C NMR(100MHz,CDCl3)δ179.6,164.8,160.5,142.5,139.7,139.5,136.0,134.7,134.2,132.4,128.1,53.0,52.8；ESI-HRMS m/z calcd For C13H10O5S2+H(M+H):311.0042,found 311.0052.
产物Ⅰ-22为棕色油，产率为53％.1H NMR(300MHz,CDCl3)δ8.13(s,1H),4.00(s,3H),3.89(s,3H),2.84(t,J＝7.4Hz,2H),1.71–1.67(m,2H),1.40–1.15(m,16H),0.88(t,J＝6.6Hz,3H)；13C NMR(75MHz,CDCl3)δ193.2,165.1,160.2,140.4,138.8,136.2,132.1,62.0,61.9,39.3,31.8,29.5,29.3(2C),29.2,29.1,23.8,22.6,14.0,13.8；ESI-HRMS m/zcalcd For C20H30O5S+H(M+H):383.1887,found383.1901.
产物Ⅰ-23为无色油，产率为25％.1H NMR(400MHz,CDCl3)δ8.28(s,1H),7.88–7.84(m,4H),7.52–7.47(m,3H),5.44(s,2H),3.88(s,3H),3.78(s,3H)；13C NMR(100MHz,CDCl3)δ165.2,160.6(2C),139.5,138.2,133.2,133.1,132.4,131.8,131.6,128.5,128.0,127.7(2C),126.4(2C),126.0,67.5,53.0,52.8；ESI-HRMS m/z calcd For C20H16O6S+Na(M+Na):407.0560,found 407.0573.
产物Ⅰ-24为棕红色油，产率为47％.1H NMR(400MHz,(CD3)2CO)δ8.45(s,1H),7.90–7.86(m,2H),7.80–7.72(m,4H),7.69–7.63(m,1H),7.63–7.58(m,1H),7.55–7.49(m,3H),7.47–7.42(m,2H),7.40–7.36(m,2H)；13C NMR(100MHz,(CD3)2CO)δ192.0,189.5,187.9,147.5,142.8,141.9,138.7,138.6,138.1,134.0(2C),133.7,130.4,129.9,129.6,129.5,129.4,129.2,(1C missing)；ESI-HRMS m/z calcd For C25H16O3S+H(M+H):397.0893,found397.0910.
产物Ⅰ-25为黄色油，产率为72％.1H NMR(400MHz,CDCl3)δ7.84–7.79(m,2H),7.65–7.59(m,2H),7.48(t,J＝7.8Hz,2H),4.42(q,J＝7.1Hz,2H),1.41(t,J＝7.2Hz,3H)；13C NMR(100MHz,CDCl3)δ190.1,159.7,141.3(q,J＝2.2Hz),136.8(q,J＝3.0Hz),136.5,134.0,131.6(q,J＝36.5Hz),131.0,129.8,128.7,120.8(q,J＝271.4Hz),62.6,13.9；19F NMR(376MHz,CDCl3)δ-55.6；ESI-HRMS m/z calcd For C15H17F3O3S+H(M+H):329.0454,found329.0467.
最后应说明的是：以上所述仅为本发明的优选实施例而已，并不用于限制本发明，尽管参照前述实施例对本发明进行了详细的说明，对于本领域的技术人员来说，其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换。凡在本发明的内容和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (5)

1.多取代噻吩其特征结构如Ⅰ所示，含有三个吸电子基团，Y可以为吸电子基团或者氢。
Figure FDA0002306833030000011
2.根据权利要求1所述的多取代噻吩，制备方法如下：
Figure FDA0002306833030000012
将通式原料含硫内鎓盐A和缺电子的炔B在二氯乙烷中混合，在85度加热，待反应物B完全消失，将反应物浓缩旋干、柱色谱分离得到目标分子多取代噻吩；
其中
X选自H、Me、OMe或者NMe2，优选OMe
EWG1选自：CO2Me,CO2Et,COPh,CF3
EWG2选自：CO2Me,CO2Et,COPh
EWG3选自：COR1,R1＝C6H5,(CH2)10CH3,OEt,4-BrC6H4,2-Naphthnyl,2-Thienyl,2-Furyl,O-2-Naphthnyl
Y选自:CO2Me,CONMePh,CH(OEt)2,COPh,CO(CH2)10CH3,CO2Et,CF3,CF2-4-BrC6H4,CHFMe,SCF3,H。
3.如权利要求2所述的方法，其特征在于，加热温度为85℃。
4.如权利要求2所述的方法，其特征在于，反应物A与反应物B的摩尔比为1.5:1。
5.如权利要求2所述的方法,其特征在于，所述溶剂二氯乙烷(DCE)的浓度优选0.1M。
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CN113173908A (zh) * 2021-04-27 2021-07-27 江西师范大学 一种噻吩类化合物的制备方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113173908A (zh) * 2021-04-27 2021-07-27 江西师范大学 一种噻吩类化合物的制备方法
CN113173908B (zh) * 2021-04-27 2022-05-27 江西师范大学 一种噻吩类化合物的制备方法

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