CN114213361A - 一种硫胺化1,4-萘醌化合物的制备方法 - Google Patents

一种硫胺化1,4-萘醌化合物的制备方法 Download PDF

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CN114213361A
CN114213361A CN202111656089.3A CN202111656089A CN114213361A CN 114213361 A CN114213361 A CN 114213361A CN 202111656089 A CN202111656089 A CN 202111656089A CN 114213361 A CN114213361 A CN 114213361A
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熊力
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Abstract

本申请公开了化学合成领域中的一种硫胺化1,4‑萘醌化合物的制备方法，制备时，将1,4‑萘醌、硫醇、胺和溶剂加入反应器中，在空气中加热至70℃，搅拌条件下反应4～6小时，得到1,4‑萘醌硫胺化产物。其中，硫胺化1,4‑萘醌化合物的结构式如下：
Figure DDA0003448323910000011
R1为取代苯基、环己基或者苄基；R2为四氢吡咯或吗啉。本方法不需要添加当量的金属添加剂，且在空气中进行，反应时间短，可高效合成硫胺化1，4‑萘醌化合物。

Description

一种硫胺化1,4-萘醌化合物的制备方法
技术领域
本发明涉及化学合成领域，具体涉及一种硫胺化1,4-萘醌化合物的制备方法。
背景技术
硫胺化1,4-萘醌化合物具有广泛的生物活性的一类重要有机化合物，在抗病毒、抗疟疾、抗炎及抗菌等领域都有着重要的应用。然而，现有的硫胺化1,4-萘醌化合物合成技术存在的一定的问题，如需要用相对较复杂的卤代萘醌为起始原料(如：RSC Adv,2014,4,12441-12447.Acc Chem Res,2015,48,1756-1766.)，反应效率也相对较低，底物适用性也有较大的局限性，同时，需要用到复杂的金属催化体系，不利于后续的应用。
基于此，现有技术CN 109574959 A公开了一种硫胺化1,4-萘醌化合物及其制备方法，所述的硫胺化1,4-萘醌化合物的制备方法，步骤如下：将催化剂、1,4-萘醌、硫醇、胺和溶剂加入反应管中，随后排尽空气，通入一个大气压的氧气，加热100℃、搅拌条件下反应10小时，得到1,4-萘醌硫胺化产物。但是该反应的条件较为苛刻，需要排尽空气，用铜催化剂，在氧气氛围下加热到100℃，并且反应时间也相对较长。
发明内容
本发明针对现有技术的不足，设计一种环境友好、无催化剂的绿色合成方法。
本发明的目的之一是提供一种硫胺化1,4-萘醌化合物的制备方法，制备的步骤如下，将1,4-萘醌、硫醇、胺和溶剂加入反应器中，在空气中加热至70℃，搅拌条件下反应4～6小时，得到硫胺化1,4-萘醌化合物。
进一步的，硫胺化1,4-萘醌化合物的结构式如下
Figure BDA0003448323900000011
其中，R1为取代苯基、环己基或者苄基；R2为四氢吡咯或吗啉。
进一步，所述硫醇的结构式如下：
R1SH；
所述胺的结构式如下：
Figure BDA0003448323900000021
进一步，所述1,4-萘醌、硫醇和胺的摩尔比1:1.5～2:1.5～2。
进一步，所述溶剂为环戊基甲醚。环戊基甲醚简称CPME。
本发明的目的之二是提供一种硫胺化1,4-萘醌化合物，硫胺化1,4-萘醌化合物的结构式如下：
Figure BDA0003448323900000022
其中，R1为取代苯基、环己基或者苄基；R2为四氢吡咯或吗啉。
进一步，化合物的结构式如下：
Figure BDA0003448323900000023
本发明的制备方法的反应通式如下：
Figure BDA0003448323900000024
本发明的有益效果是：本发明提供了一种一步实现1，4-萘醌硫胺化的制备方法，该方法不需要添加当量的金属添加剂，且在空气中进行，反应时间短，可高效合成硫胺化1,4-萘醌化合物，该方法所涉及的操作简便安全、具有反应条件简单、经济性好、环境友好的优点。
具体实施方式
下面通过具体实施方式进一步详细说明：
实施例1
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、对甲基苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物52mg，产率为75％。
Figure BDA0003448323900000031
2-(pyrrolidin-1-yl)-3-(p-tolylthio)naphthalene-1,4-dione
Reddish brown solid,75％yield(52mg).1H NMR(400MHz,Chloroform-d)δ8.10(dd,J＝7.6,1.3Hz,1H),7.93(dd,J＝7.6,1.3Hz,1H),7.69(td,J＝7.6,1.5Hz,1H),7.60(td,J＝7.5,1.3Hz,1H),7.07(d,J＝8.3Hz,2H),7.03(d,J＝8.3Hz,2H),3.95–3.84(m,4H),2.28(s,3H),1.87–1.75(m,4H).13C NMR(101MHz,Chloroform-d)δ184.39,180.29,155.61,135.06,134.78,134.09,133.48,131.96,131.90,129.59,126.40,126.25,125.90,105.66,53.82,25.50,20.93.
实施例2
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、间甲基苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物41mg，产率为58％。
Figure BDA0003448323900000032
2-(pyrrolidin-1-yl)-3-(m-tolylthio)naphthalene-1,4-dione
Reddish brown solid,58％yield(41mg),mp 50.8–51.2℃.1H NMR(400MHz,Chloroform-d)δ8.12–8.04(m,1H),7.92(dd,J＝7.6,1.3Hz,1H),7.67(td,J＝7.5,1.4Hz,1H),7.59(td,J＝7.5,1.4Hz,1H),7.08(t,J＝7.6Hz,1H),6.97(d,J＝1.7Hz,1H),6.95–6.90(m,1H),6.87(d,J＝7.5Hz,1H),3.96–3.82(m,4H),2.26(s,3H),1.87–1.71(m,4H).13CNMR(101MHz,Chloroform-d)δ184.44,180.23,155.89,138.51,134.12,133.48,131.98,131.91,128.68,126.48,126.42,125.92,125.88,122.98,104.85,53.87,25.50,21.47.HRMS Calcd for C27H20NO2S[M+H]+:m/z 350.1209,found:350.1213.
实施例3
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、2-甲基苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物39mg，产率为56％。
Figure BDA0003448323900000041
2-(pyrrolidin-1-yl)-3-(o-tolylthio)naphthalene-1,4-dione
Reddish brown solid,56％yield(39mg),mp 80.8–81.0℃.1H NMR(400MHz,Chloroform-d)δ8.09(dd,J＝7.8,1.3Hz,1H),7.93(dd,J＝7.8,1.3Hz,1H),7.68(td,J＝7.6,1.4Hz,1H),7.60(td,J＝7.5,1.3Hz,1H),7.11(dd,J＝7.1,1.7Hz,1H),7.06–6.94(m,2H),6.87(dd,J＝7.6,1.6Hz,1H),3.95–3.82(m,4H),2.45(s,3H),1.85–1.75(m,4H).13CNMR(101MHz,Chloroform-d)δ184.44,180.18,156.55,137.67,134.43,134.15,133.52,132.02,131.91,130.07,126.44,126.34,125.94,125.20,124.52,103.82,53.78,25.49,20.02.HRMS Calcd for C27H20NO2S[M+H]+:m/z 350.1209,found:350.1208.
实施例4
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、4-叔丁基苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物41mg，产率为58％。
Figure BDA0003448323900000042
2-((4-(tert-butyl)phenyl)thio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione
Reddish brown solid,71％yield(56mg).1H NMR(400MHz,Chloroform-d)δ8.07(d,J＝7.7Hz,1H),7.91(d,J＝7.6Hz,1H),7.66(t,J＝7.5Hz,1H),7.57(t,J＝7.5Hz,1H),7.22(d,J＝8.4Hz,2H),7.07(d,J＝8.4Hz,2H),3.89–3.86(m,4H),1.85–1.68(m,4H),1.25(s,9H).13C NMR(101MHz,Chloroform-d)δ184.40,180.29,155.69,148.03,135.03,134.07,133.46,131.95,131.90,126.36,125.91,125.89,125.84,105.52,53.85,34.33,31.33,25.48.
实施例5
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、4-甲氧基苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物47mg，产率为65％。
Figure BDA0003448323900000051
2-((4-methoxyphenyl)thio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione
Reddish brown solid,65％yield(47mg).1H NMR(400MHz,Chloroform-d)δ8.08(dd,J＝7.6,1.3Hz,1H),7.90(dd,J＝7.6,1.4Hz,1H),7.66(td,J＝7.5,1.4Hz,1H),7.58(td,J＝7.5,1.3Hz,1H),7.16–7.08(m,2H),6.81–6.72(m,2H),3.91–3.82(m,4H),3.74(s,3H),1.85–1.74(m,4H).13C NMR(101MHz,Chloroform-d)δ184.35,180.43,157.80,155.15,134.05,133.43,131.90,129.11,128.42,126.34,125.88,114.58,107.21,55.35,53.83,25.52.
实施例6
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、间甲氧基苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物39mg，产率为54％。
Figure BDA0003448323900000052
2-((3-methoxyphenyl)thio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione
Reddish brown solid,54％yield(39mg),mp 38.8–39.2℃.1H NMR(400MHz,Chloroform-d)δ8.07(dd,J＝7.6,1.2Hz,1H),7.89(dd,J＝7.6,1.2Hz,1H),7.66(td,J＝7.4,1.4Hz,1H),7.57(td,J＝7.6,1.4Hz,1H),7.11(t,J＝8.0Hz,1H),6.78–6.67(m,2H),6.61(dd,J＝8.1,2.4Hz,1H),3.97–3.82(m,4H),3.71(s,3H),1.90–1.71(m,4H).13C NMR(101MHz,Chloroform-d)δ184.39,180.10,159.88,156.11,140.32,134.12,133.43,131.96,131.92,129.65,126.36,125.91,118.18,111.41,110.57,104.16,55.20,53.88,25.47.HRMS Calcd for C21H20NO3S[M+H]+:m/z 366.1158,found:366.1160.
实施例7
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、2-甲基苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物55mg，产率为76％。
Figure BDA0003448323900000061
2-((2-methoxyphenyl)thio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione
Reddish brown solid,76％yield(55mg).1H NMR(400MHz,Chloroform-d)δ8.08(dd,J＝7.6,1.3Hz,1H),7.92(dd,J＝7.8,1.3Hz,1H),7.67(td,J＝7.6,1.4Hz,1H),7.59(td,J＝7.5,1.3Hz,1H),7.08–7.03(m,1H),6.90–6.78(m,3H),3.92–3.89(m,7H),1.85–1.74(m,4H).13C NMR(101MHz,Chloroform-d)δ184.50,180.09,156.73,155.51,134.11,133.59,132.03,131.85,127.10,126.42,126.37,125.90,125.61,121.16,110.36,103.00,55.87,53.80,25.50.
实施例8
在25mL的反应管中加入1，4-萘醌0.2mmol，溶剂CPME 1.5mL、4-氟苯硫醇0.3mmol，四氢吡咯0.3mmol，在空气中加热至反应温度为70℃，反应6小时后，硅胶柱层析分离得到最终产物42mg，产率为60％。
Figure BDA0003448323900000062
2-((4-fluorophenyl)thio)-3-(pyrrolidin-1-yl)naphthalene-1,4-dione
Reddish brown solid,60％yield(42mg).1H NMR(400MHz,Chloroform-d)δ8.07(dd,J＝7.5,1.2Hz,1H),7.91(dd,J＝7.6,1.3Hz,1H),7.68(td,J＝7.5,1.4Hz,1H),7.59(td,J＝7.5,1.3Hz,1H),7.18–7.08(m,2H),6.97–6.87(m,2H),3.95–3.83(m,4H),1.88–1.77(m,4H).13C NMR(101MHz,Chloroform-d)δ184.33,180.21,162.03,159.60,156.04,134.20,133.88,133.84,133.35,132.01,131.89,127.92,127.85,126.38,125.97,116.02,115.80,105.03,54.03,25.50.19F NMR(376MHz,Chloroform-d)δ-117.70.
本发明制备的化合物，具有独特的生物活性和抗菌性能，广泛应用于有机合成化学、生物化学以及药物化学等领域。
以上所述的仅是本发明的实施例，方案中公知的具体结构及特性等常识在此未作过多描述。应当指出，对于本领域的技术人员来说，在不脱离本发明结构的前提下，还可以作出若干变形和改进，这些也应该视为本发明的保护范围，这些都不会影响本发明实施的效果和专利的实用性。本申请要求的保护范围应当以其权利要求的内容为准，说明书中的具体实施方式等记载可以用于解释权利要求的内容。

Claims (7)

1.一种硫胺化1,4-萘醌化合物的制备方法，其特征在于，制备的步骤如下，将1,4-萘醌、硫醇、胺和溶剂加入反应器中，在空气中加热至70℃，搅拌条件下反应4～6小时，得到硫胺化1,4-萘醌化合物。
2.根据权利要求1所述的一种硫胺化1,4-萘醌化合物的制备方法，其特征在于：硫胺化1,4-萘醌化合物的结构式如下
Figure FDA0003448323890000011
其中，R1为取代苯基、环己基或者苄基；R2为四氢吡咯或吗啉。
3.根据权利要求2所述的一种硫胺化1,4-萘醌化合物的制备方法，其特征在于：所述硫醇的结构式如下：
R1SH；
所述胺的结构式如下：
Figure FDA0003448323890000012
4.根据权利要求3所述的一种硫胺化1,4-萘醌化合物的制备方法，其特征在于：所述1,4-萘醌、硫醇和胺的摩尔比1:1.5～2:1.5～2。
5.根据权利要求4所述的一种硫胺化1,4-萘醌化合物的制备方法，其特征在于：所述溶剂为环戊基甲醚。
6.根据权利要求1～5任一所述方法制备的硫胺化1,4-萘醌化合物，其特征在于：硫胺化1,4-萘醌化合物的结构式如下：
Figure FDA0003448323890000013
其中，R1为取代苯基、环己基或者苄基；R2为四氢吡咯或吗啉。
7.根据权利要求6所述的硫胺化1,4-萘醌化合物，其特征在于：化合物的结构式如下：
Figure FDA0003448323890000021
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