CN106565594A - 一种无过渡金属催化的2‑苯基吡啶化合物的合成方法 - Google Patents

一种无过渡金属催化的2‑苯基吡啶化合物的合成方法 Download PDF

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CN106565594A
CN106565594A CN201610942701.6A CN201610942701A CN106565594A CN 106565594 A CN106565594 A CN 106565594A CN 201610942701 A CN201610942701 A CN 201610942701A CN 106565594 A CN106565594 A CN 106565594A
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phenylpyridine
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pyridine
formic acid
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冯秀娟
张西涛
包明
周川成
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Dalian University of Technology
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Abstract

本发明涉及医药化工中间体的制备方法，涉及一种无过渡金属催化的2‑苯基吡啶化合物的合成方法。2‑苯基吡啶化合物是许多药物和生物活性分子的重要组成部分，在有机合成及药物化学等领域有着重要的应用，具有广阔的市场前景。本项目涉及一种无过渡金属催化的2‑苯基吡啶衍生物的合成方法，该方法以吡啶‑2‑甲酸和苯为原料，在碱及自由基引发剂的存在下，在温和的条件下合成2‑苯基吡啶化合物。该发明专利的方法具有步骤简单、原料易得、反应条件温和等优点。本发明具有较大的使用价值和社会经济效益。

Description

一种无过渡金属催化的2-苯基吡啶化合物的合成方法
技术领域
本发明涉及医药化工中间体的制备方法，涉及一种无过渡金属催化的2-苯基吡啶化合物的合成方法。
背景技术
2-苯基吡啶化合物不但是医药、农药、染料、功能材料、香料和天然产物等重要结构组成部分，而且也是有机合成重要的中间体。制备2-苯基吡啶化合物的方法有很多种，最经典方法是利用2-吡啶金属有机化合物与芳基卤代物的反应，然而2-吡啶金属有机化合物合成困难且不稳定，使该反应受到一定限制。同时，该反应还会产生有毒和化学计量的副产物。
羧酸衍生物因其廉价易得、容易储存和处理而成为取代有机金属试剂的理想选择。自从Nilsson首次报道通过脱羧偶联合成联芳基化合物后，脱羧偶联反应得到了迅速的发展。在过渡金属和氧化剂的共同作用下，可以通过脱羧偶联合成2-苯基吡啶化合物。
（1）经典Suzuki–Miyaura反应合成2-苯基吡啶化合物的方法
1995年Norio Miyaura和Akira Suzuki等人报道了一种钯催化的有机硼化物的偶联反应。在此基础上，Gary A.Molander等人在2004年用此方法实现了2-苯基吡啶的合成[参见：J.Org.Chem.,2003,68,4302]。通过2-溴吡啶与芳基硼化物的交叉偶联反应生成2-苯基吡啶。该方法虽简单易行，不涉及复杂的化学反应历程，但是反应过程中会产生有毒和化学计量的副产物，不符合绿色化学和可持续发展的原则。如反应式（1）所示：
（2）2013年Yangjie Wu等报道了一种通过钯催化的2-吡啶甲酸的脱羧芳基化反应合成2-苯基吡啶衍生物的方法[参见：Chem.Commun.2013,49,312-314.]。但该方法不但使用昂贵金属做催化剂且需要铜盐作为添加剂，而且条件苛刻，需要高温。如反应式（2）所示：
因此，目前尚未有一种经济、简单、温和的方法来构建2-苯基吡啶化合物。所以开发一种新的合成方法来构建2-苯基吡啶化合物具有重要意义。
发明内容
本发明的目的是提供一种步骤简单、原料易得的合成2-苯基吡啶化合物的新方法。该方法条件温和，没有过渡金属参与，经济又环保。
本发明的技术方案：
一种无过渡金属催化的2-苯基吡啶化合物的合成方法，步骤如下：
以吡啶-2-甲酸和苯为原料，在自由基引发剂和碱的存在下，以苯为溶剂加热反应，生成一系列含C-C键的2-苯基吡啶化合物，反应式如下：
式中：R选自氢、烷基、卤素、酯基中的一种；
反应时间为2-30h，优选15-25h。
所述的自由基引发剂为NBS、过氧化苯甲酰、TBHP、次氯酸酯中的一种或两种以上混合，其加入量为吡啶-2-甲酸的100-300mol%；
所述的碱为碳酸钾、碳酸钠、碳酸铯、碳酸氢钠、磷酸钾、三乙胺中的一种或两种以上混合，其加入量为吡啶-2-甲酸的10-200mol%；
作为溶剂的苯的加入量为吡啶-2-甲酸的30eq-90eq；
反应温度为40-100℃。
本发明的有益效果：2-苯基吡啶化合物是许多药物和生物活性分子的重要组成部分，在有机合成及药物化学等领域有着重要的应用，具有广阔的市场前景。本发明涉及一种2-苯基吡啶化合物的合成方法，该方法以吡啶-2-甲酸和苯为原料，自由基引发剂和碱的存在下，合成一系列2-苯基吡啶化合物。该方法具有步骤简单、原料易得等优点。本发明具有较大的使用价值和社会经济效益。
附图说明
图1为化合物2a的1H-NMR谱图。
图2为化合物2a的13C-NMR谱图。
图3为化合物2b的1H-NMR谱图。
图4为化合物2b的13C-NMR谱图。
图5为化合物2c的1H-NMR谱图。
图6为化合物2c的13C-NMR谱图。
图7为化合物2d的1H-NMR谱图。
图8为化合物2d的13C-NMR谱图。
图9为化合物2e的1H-NMR谱图。
图10为化合物2e的13C-NMR谱图。
图11为化合物2f的1H-NMR谱图。
图12为化合物2f的13C-NMR谱图。
图13为化合物2g的1H-NMR谱图。
图14为化合物2g的13C-NMR谱图。
具体实施方式
下面结合实施例子进一步说明本发明以及本发明方法进行的方式。这些实施例子仅是为了进一步阐述本发明而非本发明的保护范围仅限于此。
实施例1：2-phenyl pyridine(2a)的合成
称取吡啶-2-甲酸（36.9mg,0.3mmol）、碳酸钾（20.8mg,0.15mmol），并依次加入苯（3mL）、次氯酸叔丁酯（102μL，0.9mmol）到25mL的Schlenk反应瓶中，然后置于60℃油浴中反应20h。反应结束后，减压除去溶剂，使用石油醚/乙酸乙酯作为洗脱剂，硅胶柱分离，2-phenyl pyridine的收率为86%。1HNMR(400MHz,CDCl3):δ8.70(dt,J=4.8,1.4Hz,1H),8.03-7.96(m,2H),7.77-7.69(m,2H),7.51-7.45(m,2H),7.45-7.38(m,1H),7.25-7.16(m,1H)；13CNMR(100MHz,CDCl3):δ157.5,149.7,139.4,136.8,128.9,128.7,126.9,122.1,120.6.
实施例2：4-Chloro-2-phenylpyridine(2b)的合成
称取4-氯吡啶-2-甲酸（36.9mg,0.3mmol）、碳酸钾（41.6mg,0.3mmol），并依次加入苯（5mL）、次氯酸叔丁酯（34μL，0.3mmol）到25mL的Schlenk反应瓶中，然后置于40℃油浴中反应15h。反应结束后，减压除去溶剂，使用石油醚/乙酸乙酯作为洗脱剂，硅胶柱分离，4-Chloro-2-phenylpyridine的收率为75%。1H NMR(400MHz,CDCl3):δ=8.57(d,J=5.3Hz,1H),7.96(dt,J=8.4,2.1Hz,2H),7.72(d,J=1.9Hz,1H),7.48-7.43(m,3H),7.23(dd,J=5.3,1.9Hz,1H);13C NMR(100MHz,CDCl3):δ159.0,150.5,144.8,138.1,129.6,128.9,127.0,122.3,120.9.
实施例3：3-methyl-2-phenylpyridine(2c)的合成
称取3-甲基吡啶-2-甲酸（36.9mg,0.3mmol）、磷酸钾（127.4mg,0.6mmol），并依次加入苯（1mL）、次氯酸叔丁酯（68μL，0.6mmol）到25mL的Schlenk反应瓶中，然后置于80℃油浴中反应8h。反应结束后，减压除去溶剂，使用石油醚/乙酸乙酯作为洗脱剂，硅胶柱分离，3-methyl-2-phenylpyridine的收率为71%。1H NMR(400MHz,CDCl3):δ8.53(dd,J=4.7,1.1Hz,1H),7.57(dd,J=7.7,0.9Hz,1H),7.53-7.49(m,2H),7.47-7.34(m,3H),7.17(dd,J=7.7,4.8Hz,1H),2.34(s,3H);13C NMR(100MHz,CDCl3):δ158.7,147.0,140.6,138.5,130.8,128.9,128.1,127.9,122.1,20.0.
实施例4：4-methyl-2-phenylpyridine(2d)的合成
称取4-甲基吡啶-2-甲酸（36.9mg,0.3mmol）、碳酸钠（15.9mg,0.15mmol），并依次加入苯（10mL）、NBS（160.2mg，0.9mmol）到25mL的Schlenk反应瓶中，然后置于60℃油浴中反应5h。反应结束后，减压除去溶剂，使用石油醚/乙酸乙酯作为洗脱剂，硅胶柱分离，4-methyl-2-phenylpyridine的收率为75%。1H NMR(400MHz,CDCl3):δ8.54(d,J=5.8Hz,1H),7.98-7.96(m,2H),7.52(s,1H),7.47-7.37(m,3H),7.04(d,J=5.8Hz,1H),2.38(s,3H)；13CNMR(100MHz,CDCl3):δ157.4,149.4,147.8,139.5,128.8,128.8,126.9,123.1,121.5,21.2.
实施例5：5-Methyl-2-phenylpyridine(2e)的合成
称取5-甲基吡啶-2-甲酸（36.9mg,0.3mmol）、碳酸氢钠（25.2mg,0.3mmol），并依次加入苯（8mL）、过氧化苯甲酰（218.1mg，0.9mmol）到25mL的Schlenk反应瓶中，然后置于50℃油浴中反应12h。反应结束后，减压除去溶剂，使用石油醚/乙酸乙酯作为洗脱剂，硅胶柱分离，5-Methyl-2-phenylpyridine的收率为69%。1H NMR(400MHz,CDCl3):δ8.51(s,1H),7.97(d,J=7.2Hz,2H),7.61(d,J=8.0Hz,1H),7.53-7.42(m,3H),7.40-7.35(m,1H),2.34(s,3H);13C NMR(100MHz,CDCl3):δ154.8,150.1,139.4,137.3,131.6,128.7,128.6,126.7,120.0,18.2ppm.
实施例6：2-Methyl-6-phenylpyridine的合成
称取6-甲基吡啶-2-甲酸（36.9mg,0.3mmol）、碳酸钾（8.3mg,0.06mmol），并依次加入苯（6mL）、TBHP（86μL，0.9mmol）到25mL的Schlenk反应瓶中，然后置于40℃油浴中反应20h。反应结束后，减压除去溶剂，使用石油醚/乙酸乙酯作为洗脱剂，硅胶柱分离，2-Methyl-6-phenylpyridine(2f)的收率为64%。1H NMR(400MHz,CDCl3):δ7.98(d,J=7.1Hz,2H),7.62(t,J=7.7Hz,1H),7.50(d,J=7.8Hz,1H),7.47(t,J=7.4Hz,2H),7.38-7.35(m,1H),7.08(d,J=7.6Hz,1H),2.62(s,3H);13C NMR(100MHz,CDCl3):δ158.4,157.0,139.8,136.9,128.7,128.7,127.0,121.6,117.6,24.8.
实施例7：Methyl 6-phenylnicotinate(2g)的合成
称取5-甲酸甲酯吡啶-2-甲酸（36.9mg,0.3mmol）、碳酸钾（20.8mg,0.15mmol），并依次加入苯（2mL）、次氯酸叔丁酯（34μL，0.3mmol）到25mL的Schlenk反应瓶中，然后置于60℃油浴中反应20h。反应结束后，减压除去溶剂，使用石油醚/乙酸乙酯作为洗脱剂，硅胶柱分离，Methyl 6-phenylnicotinate(2g)的收率为46%。1H NMR(400MHz,CDCl3):δ9.28(d,J=2.2Hz,1H),8.34(dd,J=8.3,2.2Hz,1H),8.06-8.03(m,2H),7.81(d,J=8.3Hz,1H),7.52-7.45(m,3H),3.96(s,3H);13C NMR(100MHz,CDCl3):δ165.9,160.9,151.0,138.3,137.9,130.0,128.9,127.4,124.2,119.9,53.4.

Claims (5)

1.一种无过渡金属催化的2-苯基吡啶化合物的合成方法，其特征步骤如下：
以吡啶-2-甲酸和苯为原料，在自由基引发剂和碱的存在下，以苯为溶剂加热反应，生成一系列含C-C键的2-苯基吡啶化合物，反应式如下：
其中：R选自氢、烷基、卤素、酯基中的一种；
自由基引发剂的加入量为吡啶-2-甲酸的100～300mol％；
碱的加入量为吡啶-2-甲酸的10～200mol％；
苯的加入量为吡啶-2-甲酸的30q～90eq；
反应温度为40-100℃，反应时间为2-30h。
2.根据权利要求1所述的合成方法，其特征在于，所述的自由基引发剂为NBS、过氧化苯甲酰、TBHP、次氯酸酯中的一种或两种以上混合。
3.根据权利要求1或2所述的合成方法，其特征在于，所述的碱为碳酸钾、碳酸钠、碳酸铯、碳酸氢钠、磷酸钾、三乙胺中的一种或两种以上混合。
4.根据权利要求1或2所述的合成方法，其特征在于，所述的反应时间为15-25h。
5.根据权利要求3所述的合成方法，其特征在于，所述的反应时间为15-25h。
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