CN112939839B - 一种2-芳香酰吡咯类化合物的合成方法 - Google Patents

一种2-芳香酰吡咯类化合物的合成方法 Download PDF

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CN112939839B
CN112939839B CN202110158650.9A CN202110158650A CN112939839B CN 112939839 B CN112939839 B CN 112939839B CN 202110158650 A CN202110158650 A CN 202110158650A CN 112939839 B CN112939839 B CN 112939839B
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李�杰
王欢
邹东
周帆
帅素娟
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Zhejiang University City College ZUCC
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    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract

本发明涉及有机合成领域，公开了一种2‑芳香酰吡咯类化合物的合成方法，该方法用N‑芳香酰吡咯类化合物为原料，在碱金属催化下通过全新的重排反应，得到的一系列2‑芳香酰吡咯衍生物。本发明的合成方法工艺简单、无需过渡金属催化剂、高效环保，从而扩大其在药物中间体合成反应及有机合成反应中的应用范畴。

Description

一种2-芳香酰吡咯类化合物的合成方法
技术领域
本发明涉及有机合成领域，具体涉及一种2-芳香酰吡咯类化合物的合成方法。
背景技术
吡咯是一类非常重要的五元氮杂环结构。具有吡咯结构的衍生物广泛应用于新药研发、光电材料、化学催化、功能材料等诸多领域。其中2-芳香酰吡咯类化合物在制药领域发挥的作用不可忽视，它是常见的药物中间体，也是很多重要生物活性分子的母核结构，像托美汀(Tolmetin)、佐美酸(Zomepirac)、酮咯酸(Ketorolac)等非甾体抗炎药，均为2-芳香酰吡咯类衍生物；此外从假单胞菌中分离得到的吡咯霉素生物碱Pyoluteorin，对多重耐药菌和分枝杆菌有较高的抑制作用；而从链霉菌中分离得到的Celastramycin A则是具有多种抗菌活性的免疫抑制剂。
Figure BDA0002934807560000011
2-芳香酰吡咯类化合物的传统合成方法包括傅克酰化反应和Vilsmeier-Haack芳酰化反应。此外，还有基于使用硒代酯或硫代酯、N-酰基苯并三唑、腈盐、羧酸、苯甲醛和芳基乙醛酸作为替代酰基源的合成方法。具体如下：
傅克酰化反应合成2-芳香酰吡咯的反应式如下：
Figure BDA0002934807560000012
Vilsmeier-Haack芳酰化反应合成2-芳香酰吡咯的反应式如下：
Figure BDA0002934807560000021
金属钯催化的2-芳香酰吡咯的反应式如下：
Figure BDA0002934807560000022
但是上述方法都具有明显的局限性，包括需要化学计量甚至过量的路易斯酸以及强酸性条件、操作繁琐和化学选择性差等缺点。近年来，基于钯金属催化的吡咯与醛、腈和烯丙基酯的酰化反应，尽管取得了重要进展，但仍有改进的余地，存在使用昂贵的配体，产生金属盐副产物，反应普适性低等缺点。因此针对该类化合物发展更加绿色、高效的制备方法不仅具有非常重要的应用价值，同时基于此开发新的合成方法学的建立在理论上也具有非常重要的科学意义。
发明内容
本发明提供了一种合成2-芳香酰吡咯类化合物的方法，该合成方法以N-芳香酰吡咯类化合物为原料，在碱金属催化下通过全新的重排反应，得到的一系列2-芳香酰吡咯衍生物。其结构如下：
Figure BDA0002934807560000031
上述的2-芳香酰吡咯类化合物的制备方法如下：(ⅰ)在非质子溶剂中，将如通式(Ⅰ)所示的化合物和碱(例如六甲基二硅基胺基锂)混合，加热反应，然后从反应产物中收集式(Ⅱ)化合物。
Figure BDA0002934807560000032
其中，Ar选自苯基、取代苯基、萘基、吡啶、喹啉等芳香化合物；
式(Ⅰ)化合物和碱的摩尔比为1:3，反应温度为100～120℃，反应时间为3小时以上。
本发明的有益效果如下：本发明的2-芳香酰吡咯类化合物新的制备方法，工艺简单，无需过渡金属催化剂，对环境友好，所制备的2-芳香酰吡咯类化合物具有重要的药用价值，为此类重要化合物的合成提供了一条简洁高效的方法。
具体实施方式
下面根据优选实施例详细描述本发明，本发明的目的和效果将变得更加明白。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
本发明实施例提供的2-芳香酰吡咯类化合物的合成方法如下：
在惰性气体保护下，将式(Ⅰ)所示的化合物溶于甲苯中，在搅拌下加入六甲基二硅基胺基锂的四氢呋喃溶剂(1mol/L)，100℃加热条件下反应3个小时，然后加入3滴水萃灭反应，加入少量硅胶粉滤过，用乙酸乙酯洗涤后减压蒸干，混合物柱用层析柱分离(PE:EA＝20:1～10:1)得到产物(Ⅱ)。
Figure BDA0002934807560000041
其中，Ar选自苯基、取代苯基、萘基、吡啶、喹啉等芳香化合物；式(Ⅰ)化合物和碱的摩尔比为1:3。
以下通过实例来进一步说明。
实施例1
化合物Ⅱ-1的制备与表征：
Figure BDA0002934807560000042
在氮气保护下，将N-苯甲酰吡咯(17.1mg，0.1mmol)溶于1mL甲苯中，在搅拌下逐滴加入六甲基二硅基胺基锂的四氢呋喃溶剂(1.0mol/L，0.3mL，0.3mmol)，100℃加热条件下反应3个小时，然后加入3滴水萃灭反应，加入少量硅胶粉滤过，用乙酸乙酯洗涤后减压蒸干，混合物柱层析分离(PE:EA＝20:1～10:1)得到目标化合物Ⅱ-1，白色固体，产率81％；1HNMR(500MHz,CDCl3):δ9.84(s,1H),7.92–7.90(m,2H),7.59–7.55(m,1H),7.51–7.47(m,2H),7.17–7.15(m,1H),6.91–6.89(m,1H),6.36–6.34(m,1H).
实施例2
化合物Ⅱ-2的制备与表征：
Figure BDA0002934807560000043
制备条件同实施例1，白色固体，产率68％；1H NMR(500MHz,CDCl3):δ9.73(s,1H),7.84–7.82(m,2H),7.30–7.28(m,2H),7.14–7.13(m,1H),6.90–6.89(m,1H),6.35–6.33(m,1H),2.44(s,3H).
实施例3
化合物Ⅱ-3的制备与表征：
Figure BDA0002934807560000051
制备条件同实施例1，白色固体，产率76％；1H NMR(500MHz,CDCl3):δ10.17(s,1H),7.89–7.87(m,2H),7.52–7.50(m,2H),7.16–7.15(m,1H),6.94–6.92(m,1H),6.35–6.33(m,1H),1.37(s,9H).
实施例4
化合物Ⅱ-4的制备与表征：
Figure BDA0002934807560000052
制备条件同实施例1，白色固体，产率81％；1H NMR(500MHz,CDCl3):δ9.87(s,1H),8.02–7.99(m,2H),7.73–7.71(m,2H),7.67–7.65(m,2H),7.51–7.47(m,2H),7.42–7.39(m,1H),7.18–7.17(m,1H),6.97–6.96(m,1H),6.38–6.36(m,1H).
实施例5
化合物Ⅱ-5的制备与表征：
Figure BDA0002934807560000053
制备条件同实施例1，浅黄色固体，产率72％；1H NMR(500MHz,CDCl3):δ10.18(s,1H),7.97–7.93(m,2H),7.19–7.14(m,3H),6.88–6.87(m,1H),6.36–6.34(m,1H).
实施例6
化合物Ⅱ-6的制备与表征：
Figure BDA0002934807560000061
制备条件同实施例1，白色固体，产率78％；1H NMR(500MHz,CDCl3):δ10.05(s,1H),7.87–7.84(m,2H),7.48–7.45(m,2H),7.18–7.17(m,1H),6.88–6.86(m,1H),6.36–6.34(m,1H).
实施例7
化合物Ⅱ-7的制备与表征：
Figure BDA0002934807560000062
制备条件同实施例1，白色固体，产率74％；1H NMR(500MHz,CDCl3):δ10.42(s,1H),7.80–7.77(m,2H),7.64–7.61(m,2H),7.20–7.18(m,1H),6.88–6.86(m,1H),6.35–6.33(m,1H).
实施例8
化合物Ⅱ-8的制备与表征：
Figure BDA0002934807560000063
制备条件同实施例1，白色固体，产率70％；1H NMR(500MHz,CDCl3):δ9.85(s,1H),8.00–7.98(m,2H),7.77–7.75(m,2H),7.21–7.20(m,1H),6.88–6.86(m,1H),6.38–6.36(m,1H).
实施例9
化合物Ⅱ-9的制备与表征：
Figure BDA0002934807560000064
制备条件同实施例1，白色固体，产率75％；1H NMR(500MHz,DMSO-d):δ12.22(s,1H),8.01–7.98(m,2H),7.94–7.91(m,2H),7.30–7.28(m,1H),6.79–6.78(m,1H),6.30–6.28(m,1H).
实施例10
化合物Ⅱ-10的制备与表征：
Figure BDA0002934807560000071
制备条件同实施例1，白色固体，产率72％；1H NMR(500MHz,DMSO-d6):δ12.15(s,1H),7.95–7.92(m,2H),7.51–7.48(m,2H),7.26–7.24(m,1H),6.81–6.80(m,1H),6.29–6.27(m,1H).
实施例11
化合物Ⅱ-11的制备与表征：
Figure BDA0002934807560000072
制备条件同实施例1，黄色固体，产率84％；1H NMR(500MHz,CDCl3):δ9.99(s,1H),7.97–7.94(m,2H),7.10–7.08(m,1H),6.92–6.90(m,1H),6.73–6.70(m,2H),6.33–6.32(m,1H),3.06(s,6H).
实施例12
化合物Ⅱ-12的制备与表征：
Figure BDA0002934807560000073
制备条件同实施例1，白色固体，产率72％；1H NMR(500MHz,CDCl3):δ9.83(s,1H),7.96–7.93(m,2H),7.13–7.12(m,1H),7.00–6.97(m,2H),6.90–6.89(m,1H),6.35–6.33(m,1H),3.89(s,3H).
实施例13
化合物Ⅱ-13的制备与表征：
Figure BDA0002934807560000081
制备条件同实施例1，反应温度为120℃，反应时间为10小时，白色固体，产率84％；1H NMR(500MHz,CDCl3):δ9.74(s,1H),7.46–7.42(m,2H),7.12–7.10(m,1H),7.02–6.99(m,2H),6.65–6.63(m,1H),6.28–6.26(m,1H),3.83(s,3H).
实施例14
化合物Ⅱ-14的制备与表征：
Figure BDA0002934807560000082
制备条件同实施例1，白色固体，产率70％；1H NMR(500MHz,CDCl3):δ10.35(s,1H),7.50–7.47(m,2H),7.43–7.39(m,1H),7.36–7.32(m,1H),7.21–7.20(m,1H),6.62–6.60(m,1H),6.30–6.28(m,1H).
实施例15
化合物Ⅱ-15的制备与表征：
Figure BDA0002934807560000083
制备条件同实施例1，反应温度为120℃，反应时间为10小时，白色固体，产率71％；1H NMR(500MHz,DMSO-d6):δ11.92(s,1H),7.60–7.57(m,1H),7.50–7.45(m,3H),7.32–7.22(m,5H),7.11–7.09(m,1H),6.39–6.38(m,1H),6.12–6.11(m,1H).
实施例16
化合物Ⅱ-16的制备与表征：
Figure BDA0002934807560000084
制备条件同实施例1，反应温度为120℃，反应时间为10小时，浅黄色固体，产率85％；1H NMR(500MHz,CDCl3):δ10.48(s,1H),8.31–8.27(m,1H),8.01–7.99(m,1H),7.94–7.91(m,1H),7.80(dd,J＝7.0,1.2Hz,1H),7.56–7.52(m,3H),7.20–7.19(m,1H),6.71–6.69(m,1H),6.31–6.29(m,1H).
实施例17
化合物Ⅱ-17的制备与表征：
Figure BDA0002934807560000091
制备条件同实施例1，浅黄色固体，产率77％；1H NMR(500MHz,CDCl3):δ10.20(s,1H),8.46(s,1H),8.01–7.91(m,4H),7.62–7.55(m,2H),7.21–7.20(m,1H),7.01–6.99(m,1H),6.39–6.38(m,1H).
实施例18
化合物Ⅱ-18的制备与表征：
Figure BDA0002934807560000092
制备条件同实施例1，浅粉色固体，产率61％；1H NMR(500MHz,DMSO-d6):δ12.23(s,1H),8.96–8.95(m,1H),8.77(dd,J＝4.8,1.7Hz,1H),8.17–8.15(m,1H),7.55–7.53(m,1H),7.29–7.27(m,1H),6.83–6.81(m,1H),6.29–6.28(m,1H).
实施例19
化合物Ⅱ-19的制备与表征：
Figure BDA0002934807560000093
制备条件同实施例1，白色固体，产率73％；1H NMR(500MHz,DMSO-d6):δ12.19(s,1H),9.01(dd,J＝4.2,1.8Hz,1H),8.58(dd,J＝8.3,1.8Hz,1H),8.53(d,J＝1.6Hz,1H),8.14–8.10(m,2H),7.63(dd,J＝8.3,4.2Hz,1H),7.29–7.28(m,1H),6.94–6.93(m,1H),6.32–6.31(m,1H).
实施例20
化合物Ⅱ-20的制备与表征：
Figure BDA0002934807560000101
制备条件同实施例1，浅黄色固体，产率68％；1H NMR(500MHz,DMSO-d6):δ12.28(s,1H),9.22(d,J＝2.1Hz,1H),8.85(d,J＝2.1Hz,1H),8.19(dd,J＝8.2,1.3Hz,1H),8.10(d,J＝8.4Hz,1H),7.89–7.86(m,1H),7.71–7.67(m,1H),7.32–7.31(m,1H),6.98–6.96(m,1H),6.33–6.32(m,1H).
本领域普通技术人员可以理解，以上所述仅为发明的优选实例而已，并不用于限制发明，尽管参照前述实例对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例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。凡在发明的精神和原则之内，所做的修改、等同替换等均应包含在发明的保护范围之内。

Claims (4)

1.一种2-芳香酰吡咯类化合物的合成方法，其特征在于，在惰性气体保护下，将式(Ⅰ)所示的化合物溶于甲苯中，在搅拌下加入1mol/L的六甲基二硅基胺基锂的四氢呋喃溶液，加热条件下进行反应，然后从反应产物中收集式(Ⅱ)化合物
Figure FDA0003489032620000011
其中，Ar选自苯基、4-甲基苯基、4-叔丁基苯基、4-苯基苯基、4-氟苯基、4-氯苯基、4-溴苯基、4-三氟甲基苯基、4-氰基苯基、4-三氟甲氧基苯基、4-(二甲氨基)苯基、4-甲氧基苯基、2-甲氧基苯基、2-氯苯基、2-苯基苯基、萘基、吡啶、喹啉中的任意一种。
2.根据权利要求1所述的2-芳香酰吡咯类化合物的合成方法，其特征在于，加热反应的温度为100～120℃，反应时间为3小时以上。
3.根据权利要求1所述的2-芳香酰吡咯类化合物的合成方法，其特征在于，所述式(Ⅰ)化合物和六甲基二硅基胺基锂的摩尔比为1:3。
4.根据权利要求1所述的2-芳香酰吡咯类化合物的合成方法，其特征在于，所述加热反应通过加入3滴水淬灭 反应，并经乙酸乙酯洗涤后减压蒸干，混合物柱用层析柱分离得到产物(Ⅱ)。
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