CN114989032A - 一种酰亚胺类衍生物的合成方法 - Google Patents

一种酰亚胺类衍生物的合成方法 Download PDF

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CN114989032A
CN114989032A CN202210671658.XA CN202210671658A CN114989032A CN 114989032 A CN114989032 A CN 114989032A CN 202210671658 A CN202210671658 A CN 202210671658A CN 114989032 A CN114989032 A CN 114989032A
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宣俊
姚维忠
蔡宝贵
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Abstract

本发明公开了一种酰亚胺类衍生物的合成方法，在光照条件下，利用重氮化合物和羧酸在腈类溶剂中进行反应，重氮化合物首先在光照条件下脱去一分子氮气产生活性卡宾物种，此时腈类溶剂作为卡宾捕获试剂可产生腈叶立德中间体，被羧酸捕获之后再经过进一步的Mumm重排可获得目标酰亚胺类衍生物。本方法不需要任何催化剂以及添加剂，只需要可见光作为绿色能源进行驱动，反应条件温和，易于操作，并能通过流动光化学的方法进行大量合成。

Description

一种酰亚胺类衍生物的合成方法
技术领域
本发明属于有机合成领域，具体涉及一种酰亚胺类衍生物的合成方法。
背景技术
酰亚胺类衍生物是有机合成领域、制药领域、电镀领域、以及电化学领域等最常见和最基本的有机化合物之一。因此，高效构建酰亚胺类衍生物已成为有机和药物化学领域深入研究的课题之一。
由于酰亚胺类衍生物的应用非常广泛，因此有机合成化学家们也开发了许多合成酰亚胺类衍生物的方法。在过去几年中，通过重氮化合物与芳基偶氮盐在腈类溶剂中进行反应构建酰亚胺类衍生物引起了广大科研工作者的兴趣，然而这些反应往往需要金属催化剂的参与。因此，开发在无任何催化剂以及添加剂条件下构建酰亚胺类衍生物的方法也是一项挑战。
发明内容
本课题组通过研究发现，在蓝色LED灯的照射下，重氮化合物脱去一份子氮气产生的活性卡宾物种首先被腈类溶剂捕获产生腈叶立德中间体，被羧酸捕获之后再经过进一步的Mumm重排可获得目标酰亚胺类衍生物从而为酰亚胺类衍生物的合成提供了温和的反应途径。同时我们也尝试了使用绿色LED灯作为光源，结果表明反应速率会急速下降。
基于以上研究背景，本发明提供了一种酰亚胺类衍生物的合成方法，利用重氮化合物与羧酸化合物在腈类溶剂中进行反应，简便的制备了各种1,2,4-三氮唑衍生物。本方法不需要任何催化剂以及添加剂，只需要可见光作为绿色能源进行驱动。
本发明酰亚胺类衍生物的合成方法，将重氮化合物1、羧酸化合物2加入腈类溶剂中，在光照条件下进行反应，分离提纯后得到目标产物3。
合成路线如下所示：
Figure BDA0003693431280000011
重氮化合物1中的取代基EWG为酯基、酰胺基、三氟甲基、氰基、磷酸酯等。
羧酸化合物2中的取代基R1为烷基、芳基或杂芳基、杂环化合物等。
腈类溶剂中的取代基R2为加甲基、乙基、异丙基、叔丁基、环丁基、芳基或氘代甲基。
所述分离提纯是通过硅胶柱层析分离纯化的方式，洗脱液为石油醚和乙酸乙酯，体积比10:1-3:1。
相较于现有技术，本发明的有益效果体现在：
1、所使用的原料容易制备，并且部分重氮化合物、羧酸化合物和腈类溶剂可以商业购买。
2、无需使用任何催化剂以及添加剂，仅仅只需要普通蓝色LED灯进行光照。
3、反应条件温和，易于操作，并能通过流动光化学的方法进行大量合成。
4、氮气作为唯一副产物，符合绿色化学理念。
具体实施方式
下面结合具体实施例对本发明技术方案作进一步的详细说明。
实施例1：
Figure BDA0003693431280000021
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：87％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.76–7.69(m,2H),7.61–7.54(m,1H),7.51–7.45(m,2H),4.50(s,2H),4.21(q,J＝7.2Hz,2H),2.16(s,3H),1.28(t,J＝7.1Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.4,173.2,168.7,135.4,132.6,128.9,128.4,61.6,47.3,26.2,14.1.
实施例2：
Figure BDA0003693431280000022
在10mL反应瓶中，加入重氮化合物(0.4mmol,26.8mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：88％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.72–7.62(m,3H),7.59–7.51(m,2H),4.58(s,2H),2.22(s,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝172.2,171.9,133.9,133.5,129.3,128.4,115.0,33.7,26.0.
实施例3：
Figure BDA0003693431280000031
在10mL反应瓶中，加入重氮化合物(0.4mmol,44.0mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：81％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.73–7.59(m,3H),7.52(t,J＝8.0Hz,2H),4.58(q,J＝8.7Hz,2H),2.04(s,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.3,171.7,134.7,133.5,129.2,128.8,45.0(t,J＝69.1Hz),25.9.
实施例4：
Figure BDA0003693431280000032
在10mL反应瓶中，加入重氮化合物(0.4mmol,60.0mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：71％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.70(d,J＝7.4Hz,2H),7.62–7.56(m,1H),7.49(t,J＝7.7Hz,2H),4.36(d,J＝11.3Hz,2H),3.76(d,J＝10.9Hz,6H),2.04(s,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.4,172.2,135.3,132.9,129.0,128.8,53.0(d,J＝5.9Hz),40.8,39.3,26.1.
实施例5：
Figure BDA0003693431280000041
在10mL反应瓶中，加入重氮化合物(0.4mmol,51.3mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：76％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.75–7.69(m,2H),7.60–7.54(m,1H),7.50–7.45(m,2H),4.50(s,2H),4.12(t,J＝6.7Hz,2H),2.16(s,3H),1.70–1.63(m,2H),0.93(t,J＝7.4Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.4,173.2,168.8,135.4,132.6,128.9,128.5,47.3,26.3,21.9,10.2.
实施例6：
Figure BDA0003693431280000042
在10mL反应瓶中，加入重氮化合物(0.4mmol,51.3mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：80％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.76–7.69(m,2H),7.60–7.54(m,1H),7.50–7.44(m,2H),5.12–5.01(m,1H),4.46(s,2H),2.16(s,3H),1.25(d,J＝6.3Hz,6H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.4,173.2,168.2,135.4,132.5,128.9,128.4,69.4,47.6,26.2,21.7.
实施例7：
Figure BDA0003693431280000051
在10mL反应瓶中，加入重氮化合物(0.4mmol,56.9mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：71％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.74–7.69(m,2H),7.59–7.54(m,1H),7.49–7.44(m,2H),4.39(s,2H),2.18(s,3H),1.46(s,9H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.5,173.2,167.7,135.5,132.5,128.8,128.4,82.3,48.1,28.0,26.2.
实施例8：
Figure BDA0003693431280000052
在10mL反应瓶中，加入重氮化合物(0.4mmol,70.5mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：77％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.70–7.65(m,2H),7.57–7.52(m,1H),7.42(t,J＝7.7Hz,2H),7.37–7.31(m,5H),5.18(s,2H),4.55(s,2H),2.15(s,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.5,173.3,168.7,135.4,135.3,132.7,129.0,128.7,128.6,128.5,128.4,67.4,47.5,26.4.
实施例9：
Figure BDA0003693431280000053
在10mL反应瓶中，加入重氮化合物(0.4mmol,88.0mg)、羧酸(0.1mmol,12.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：81％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.74–7.68(m,2H),7.59–7.53(m,1H),7.49–7.44(m,2H),4.38(s,2H),2.18(s,6H),2.11(d,J＝3.0Hz,6H),1.65(s,6H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.5,173.2,167.4,135.5,132.4,128.8,128.4,82.4,48.1,41.2,36.0,30.8,26.2.
实施例10：
Figure BDA0003693431280000061
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,12.2mg)以及nBuCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：80％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.75–7.68(m,2H),7.60–7.53(m,1H),7.47(t,J＝7.5Hz,2H),4.47(s,2H),4.25–4.17(m,2H),2.44–2.36(m,2H),1.61–1.52(m,2H),1.30–1.18(m,5H),0.81(t,J＝7.4Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝176.8,173.6,168.9,135.7,132.6,128.5,61.6,47.6,38.2,27.6,22.2,13.7.
实施例11：
Figure BDA0003693431280000062
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,12.2mg)以及iPrCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：83％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.76–7.69(m,2H),7.60–7.54(m,1H),7.50–7.44(m,2H),4.46(d,J＝0.9Hz,2H),4.25–4.18(m,2H),2.89–2.76(m,1H),1.27(t,J＝7.2Hz,3H),1.09(d,J＝6.7Hz,6H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝181.6,173.5,168.7,135.6,132.6,128.9,128.5,61.5,47.8,36.0,19.6,14.11.
实施例12：
Figure BDA0003693431280000071
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,12.2mg)以及cyclopropanecarbonitrile(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝10:1]，即得到纯净的产物，无色油状，产率：90％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.82–7.76(m,2H),7.59–7.51(m,1H),7.51–7.44(m,2H),4.61(s,2H),4.25–4.19(m,2H),1.42–1.35(m,1H),1.28(t,J＝7.2Hz,3H),1.09–1.03(m,2H),0.65–0.59(m,2H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝177.5,173.4,168.9,135.9,132.5,129.1,128.7,61.5,47.0,18.6,14.1,12.1.
实施例13：
Figure BDA0003693431280000072
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,17.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：70％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝8.27(s,1H),7.97–7.8(m,3H),7.79–7.74(m,1H),7.66–7.55(m,2H),4.56(s,2H),4.27–4.19(m,2H),2.17(s,3H),1.28(t,J＝7.2Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.6,173.3,168.8,135.1,132.5,132.4,129.7,129.1,129.0,128.6,127.9,127.3,124.4,61.6,47.5,26.3,14.1.
实施例14：
Figure BDA0003693431280000081
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,16.6mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：74％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.38–7.33(m,1H),7.23(d,J＝1.7Hz,1H),6.87(d,J＝8.1Hz,1H),6.07(s,2H),4.49(s,2H),4.22(q,J＝7.1Hz,2H),2.14(s,3H),1.28(t,J＝7.1Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.0,172.7,168.8,151.7,148.3,129.1,124.8,109.0,108.4,102.1,61.6,47.4,26.0,14.1.
实施例15：
Figure BDA0003693431280000082
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,13.6mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：97％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝7.35–7.17(m,5H),4.42(s,2H),4.22–4.14(m,2H),4.01(s,2H),2.39(s,3H),1.25(t,J＝7.2Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.4,172.6,168.3,133.5,129.2,128.4,127.0,61.5,45.8,44.1,26.0,13.9.
实施例16：
Figure BDA0003693431280000091
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,12.3mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：72％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝8.62(d,J＝4.6Hz,1H),7.96–7.84(m,2H),7.50–7.44(m,1H),4.67(s,2H),4.22–4.15(m,2H),2.31(s,3H),1.26(t,J＝7.1Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝173.7,170.8,168.8,152.1,148.5,137.5,126.5,125.0,61.4,47.0,26.4,14.1.
实施例17：
Figure BDA0003693431280000092
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,17.2mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：49％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝9.16(d,J＝2.2Hz,1H),8.56(d,J＝1.4Hz,1H),8.18(d,J＝8.6Hz,1H),7.93(d,J＝8.2Hz,1H),7.90–7.84(m,1H),7.70–7.63(m,1H),4.56(s,2H),4.27–4.21(m,2H),2.26(s,3H),1.29(t,J＝7.1Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝172.7,171.5,168.5,149.4,148.6,137.1,132.1,129.6,128.9,128.3,128.0,126.6,61.9,47.5,26.2,14.1.
实施例18：
Figure BDA0003693431280000101
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,17.5mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：41％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝8.27–8.20(m,1H),7.88(s,1H),7.41–7.29(m,3H),4.26–4.19(m,2H),4.04(d,J＝5.1Hz,2H),3.86(s,3H),2.05(s,3H),1.29(t,J＝7.1Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝170.2,170.1,169.9,137.3,136.3,126.9,122.9,122.2,121.8,109.8,106.3,61.6,41.5,33.5,22.9,14.1.
实施例19：
Figure BDA0003693431280000102
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,11.3mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：75％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝8.93(s,1H),8.55(s,1H),4.44(s,2H),4.29–4.22(m,2H),2.42(s,3H),1.31(t,J＝7.1Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝172.2,168.6,163.5,160.6,148.7,117.6,62.1,47.4,25.5,14.1.
实施例20：
Figure BDA0003693431280000111
在10mL反应瓶中，加入重氮化合物(0.4mmol,45.6mg)、羧酸(0.1mmol,18.0mg)以及MeCN(1mL)于蓝光照射下进行反应，TLC(用薄层层析色谱法)检测至反应完全后减压除去有机溶剂，用硅胶柱层析分离纯化[V(石油醚)：V(乙酸乙酯)＝10:1-5:1，本实施例优选V(石油醚)：V(乙酸乙酯)＝5:1]，即得到纯净的产物，无色油状，产率：56％。
目标化合物经测试：
1H NMR(400MHz,CDCl3,300K):δ(ppm)＝6.97–6.92(m,1H),6.91–6.83(m,3H),5.58(t,J＝3.4Hz,1H),4.50–4.39(m,4H),4.25–4.18(m,2H),2.36(s,3H),1.27(t,J＝7.1Hz,3H).
13C NMR(100MHz,CDCl3,300K):δ(ppm)＝172.6,170.6,168.1,143.1,142.7,122.0,121.6,117.1,116.9,73.9,64.5,62.0,46.3,25.3,14.0.

Claims (6)

1.一种酰亚胺类衍生物的合成方法，其特征在于：
在光照条件下，利用重氮化合物1与羧酸化合物2在腈类溶剂中进行反应，重氮化合物脱去一份子氮气产生的活性卡宾物种首先被腈类溶剂捕获产生1,3-偶极子中间体，被羧酸捕获后随后经历一步Mumm重排即可获得目标产物——酰亚胺类衍生物；
合成路线如下所示：
Figure FDA0003693431270000011
2.根据权利要求1所述的合成方法，其特征在于：
反应在蓝色LED灯的照射下进行。
3.根据权利要求1所述的合成方法，其特征在于：
重氮化合物1中的取代基EWG为酯基、酰胺基、三氟甲基、氰基或磷酸酯。
4.根据权利要求1所述的合成方法，其特征在于：
羧酸化合物2中的取代基R1为烷基、芳基或杂芳基、杂环化合物。
5.根据权利要求1所述的合成方法，其特征在于：
腈类溶剂中的取代基R2为加甲基、乙基、异丙基、叔丁基、环丁基、芳基或氘代甲基。
6.根据权利要求1所述的合成方法，其特征在于：
反应结束后分离提纯获得目标产物；所述分离提纯是通过硅胶柱层析分离纯化的方式，洗脱液为石油醚和乙酸乙酯，体积比10:1-3:1。
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