CN110105285B - 三取代吡唑类衍生物及其制备方法 - Google Patents
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
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Abstract
本发明的主要目的在于提供了一种全新的三取代吡唑类衍生物及其制备方法。该方法实现了由2,5‑二氢‑1,4,5‑硫二氮卓氧化物作为起始原料,以溴化锌作路易斯酸催化剂,二氯甲烷做反应溶剂,室温条件下,便可一步简单高效的合成三取代吡唑类衍生物。
Description
技术领域
本发明涉及有机合成化学领域,具体是涉及一类三取代吡唑衍生物及其制备方法。
背景技术
吡唑是一类含有两个连续氮原子的五元杂环骨架,吡唑类衍生物因其特殊的活性在农业领域和药物领域已被证明有极好的应用价值。除此之外,吡唑类衍生物也被应用于超分子化学、聚合物化学领域,甚至是食品和化妆品领域。目前,吡唑类衍生物的合成也有所报道,其合成方法虽各有优势,但总体来看,依然存在需要使用金属催化剂,合成步骤繁琐,底物适用性低,反应时间长等缺点。因此,研究如何简洁、高效的合成吡唑类衍生物依然具有十分重要的意义。
发明内容
本发明的主要目的在于提供了一种全新的三取代吡唑类衍生物及其制备方法。该方法实现了由2,5-二氢-1,4,5-硫二氮卓氧化物作为起始原料,以溴化锌作路易斯酸,二氯甲烷做反应溶剂,室温条件下反应8小时,便可一步简单高效的合成三取代吡唑类衍生物,同时提供这类化合物的制备方法。
本发明所述的化合物是如Ⅰ所示的化合物—三取代吡唑类衍生物。
其中:R1为苯基或取代苯基(取代基包含4-甲氧基、4-甲基、4-三氟甲基、4-氟),杂环取代基,烷基取代基,烯基取代基;R2为甲基取代基或乙基取代基。
本发明的三取代吡唑类衍生物的制备方法如下所示:
目标化合物Ⅰ的制备方法:即将通式Ⅱ所示化合物、无水溴化锌粉末在室温条件下溶解于二氯甲烷溶剂中,反应物Ⅱ消失完全,将反应混合物减压条件下除去有机溶剂,柱层析洗脱得到目标化合物Ⅰ,反应物Ⅱ中:R1为苯基或取代苯基取代基(包含4-甲氧基、4-甲基、4-三氟甲基、4-氟),杂环取代基,烷基取代基,烯基取代基;R2为甲基取代基或乙基取代基。
本发明优选的三取代吡唑类衍生物的制备方法是,使用溴化锌作路易斯酸,二氯甲烷作为溶剂。
进一步,本发明优选的制备方法是:反应时化合物Ⅱ、溴化锌试剂的摩尔比(即当量比)为Ⅱ:溴化锌=1.0:1.0,二氯甲烷溶液浓度为0.1M,即0.1摩尔每升。
更进一步,本发明优选的制备方法在硅胶柱层析时,所用的洗脱液为石油醚与乙酸乙酯的混合溶剂,且体积比V石油醚:V乙酸乙酯=6:1~3:1。
本发明涉及的方法非常新颖,是通过路易斯酸催化缩环策略构建吡唑环,这在文献中很少见。得到的吡唑环为高度官能团化的三取代吡唑类衍生物,而且反应中没有使用贵重金属催化剂,反应操作简单,后处理方便,产率普遍很高,且在制备过程中无需惰性气体保护。
附图说明
图1-2为所得产物Ⅰ-1的核磁谱(氢谱和碳谱):
具体实施方式
本发明以下结合具体实施例进行解说。
本发明的制备方法是将化合物Ⅱ和溴化锌试剂溶于有机溶剂中进行反应,反应完成后除去溶剂,然后用柱层析方法得到目标化合物。实验表明本发明优选的路易斯酸为溴化锌,优选的有机溶剂为二氯甲烷,其反应产物收率普遍较高,最好的原料摩尔比为化合物Ⅱ:溴化锌试剂=1.0:1.0,溶液的最优浓度为0.1M。以下是本发明的一个制备化合物最佳实施例。在以下所有实施例中,核磁谱检测通过Varian 300,Bruker 400,JEOL 400andVarian 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4G quadrupole time-of-flight(QTof)质谱仪器得到。
实施例1
实施例1的反应式,具体使用的化合物Ⅱ-1以及产物Ⅰ-1结构如下
具体实验步骤是:将127mg(0.300mmol,1.0当量)的化合物Ⅱ-1溶于3mL的二氯甲烷中,加入68mg(0.30mmol,1.0当量)的溴化锌,于25℃反应。反应结束后,将反应混合物在水泵减压下旋转蒸发除去溶剂二氯甲烷。残留物以200-300目硅胶,洗脱液(体积比V石油醚:V乙酸乙酯=6:1~3:1)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为黄色油状液体,产率为92%.1H NMR(600MHz,CDCl3)δ7.60–7.53(m,2H),7.42–7.38(m,3H),3.83(s,3H),3.78(s,3H);13C NMR(100MHz,CDCl3)δ164.2,161.1,146.6,141.0,129.6,128.7,128.3,128.0,113.1,52.4,52.4;ESI-HRMS m/z calcd for C13H12N2O4+Na+283.0689,found 283.0688.
制备本发明的其它化合物(化合物Ⅰ-2至化合物Ⅰ-9)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Ⅱ(0.3mmol,1.0当量)溶于3mL的二氯甲烷中,加入溴化锌68mg(0.3mmol,1.0当量),室温25℃反应8小时。
所得各产物结构和数据表征如下:
产物Ⅰ-2为黄色油状液体,产率为85%.1H NMR(400MHz,CDCl3)δ7.50(d,J=7.6Hz,2H),6.90(d,J=7.6Hz,2H),3.81(s,6H),3.78(s,3H);13C NMR(100MHz,CDCl3)δ164.1,161.4,160.7,146.2,141.6,129.5,120.1,114.1,112.4,55.3,52.4,52.3;ESI-HRMS m/zcalcd for C14H14N2O5+H+291.0975,found 291.0973.
产物Ⅰ-3为黄色油状液体,产率为92%.1H NMR(400MHz,CDCl3)δ7.43(d,J=8.0Hz,2H),7.17(d,J=7.6Hz,2H),3.81(s,3H),3.74(s,3H),2.35(s,3H);13C NMR(100MHz,CDCl3)δ164.3,161.3,146.2,141.4,139.6,129.3,127.8,125.1,112.6,52.3,52.2,21.2;ESI-HRMS m/z calcd for C14H14N2O4+H+275.1026,found 275.1027.
产物Ⅰ-4为黄色油状液体,产率为81%.1H NMR(400MHz,CDCl3)δ,7.70(d,J=8.4Hz,2H),7.63(d,J=8.4Hz,2H),3.84(s,3H),3.80(s,3H);13C NMR(100MHz,CDCl3)δ164.0,160.4,146.1,139.6,132.3,131.3(q,J=32.5Hz),128.3,125.6(q,J=3.7Hz),123.8(q,J=270.6Hz),113.8,52.6,(1C missing);ESI-HRMS m/z calcd for C14H11F3N2O4+Na+351.0563,found 351.0562.
产物Ⅰ-5为黄色油状液体,产率为76%.1H NMR(400MHz,CDCl3)δ7.58–7.52(m,2H),7.06(t,J=8.8Hz,2H),3.82(s,3H),3.74(s,3H);13C NMR(100MHz,CDCl3)δ164.1,163.4(d,J=248.6Hz),161.0,145.7,140.8,130.1(d,J=8.4Hz),124.4(d,J=3.1Hz),115.8(d,J=21.7Hz),112.8,52.4(2C);ESI-HRMS m/z calcd for C13H11FN2O4+Na+301.0595,found301.0593.
产物Ⅰ-6为黄色油状液体,产率为37%.1H NMR(400MHz,CDCl3)δ7.50(d,J=1.2Hz,1H),7.24(d,J=3.2Hz,1H),6.53(dd,J=3.2,1.6Hz,1H),3.93(s,3H),3.93(s,3H);13C NMR(100MHz,CDCl3)δ163.2,161.6,143.5,142.9,142.6,137.7,112.6,112.2,110.1,52.6,52.2;ESI-HRMS m/z calcd for C11H10N2O5+Na+273.0482,found 273.0481.
产物Ⅰ-7为白色固体,产率为77%,熔点:117-118℃.1H NMR(400MHz,CDCl3)δ3.90(s,3H),3.88(s,3H),1.40(s,9H);13C NMR(100MHz,CDCl3)δ165.6,161.7,153.3,141.5,112.7,52.3,52.1,32.4,29.0;ESI-HRMS m/z calcd for C11H16N2O4+Na+263.1002,found263.1001.
产物Ⅰ-8为白色固体,产率为63%,熔点:117.5-118.3℃.1H NMR(400MHz,CDCl3)δ7.48(d,J=7.2Hz,2H),7.40–7.28(m,5H),3.93(s,3H),3.70(s,3H);13C NMR(100MHz,CDCl3)δ163.2,161.7,145.1,142.8,135.6,134.3,129.0,128.7,127.1,113.7,111.5,52.4,52.0;ESI-HRMS m/z calcd for C15H14N2O4+Na+309.0846,found 309.0845.
产物Ⅰ-9为黄色油状液体,产率为91%.1H NMR(400MHz,CDCl3)δ7.60–7.52(m,2H),7.39–7.33(m,3H),4.29(q,J=7.2Hz,2H),4.18(q,J=7.2Hz,2H),1.26(t,J=7.2Hz,3H),1.18(t,J=7.2Hz,3H);13C NMR(100MHz,CDCl3)δ163.8,160.7,146.1,141.0,129.3,128.5,128.4,127.9,113.3,61.4,61.3,13.9,13.9;ESI-HRMS m/z calcd for C15H16N2O4+Na+311.1002,found 311.1002。
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 (3)
2.根据权利要求1所述的三取代吡唑类衍生物的制备方法,其特征在于化合物Ⅱ、无水溴化锌的摩尔比为化合物Ⅱ:溴化锌=1.0:1.0。
3.根据权利要求1或2所述的三取代吡唑类衍生物的制备方法,其特征在于硅胶柱层析所用的洗脱液为石油醚与乙酸乙酯的混合溶剂,且体积比V石油醚:V乙酸乙酯=6:1~3:1即可得到目标化合物Ⅰ。
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