CN108947995B - 一种多取代噁二嗪衍生物的制备方法 - Google Patents
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Abstract
本发明公开了属于有机合成技术领域的一种多取代噁二嗪衍生物的制备方法。所述方法为:向反应容器中,先后加入取代苄胺肟、取代苯乙炔基碘鎓盐和氢氧化钾,加入溶剂四氢呋喃,室温下搅拌至反应4小时完毕后,使用旋转蒸发仪浓缩滤液得到粗产物,粗产物用硅胶柱层析分离得到目标化合物。本发明提供的噁二嗪衍生物的合成方法具有科学合理,合成方法简单,反应条件温和,产物易于纯化等特点。其反应方程式如下:
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种多取代噁二嗪衍生物的制备方法。
背景技术
噁二嗪类化合物是较少探索的含N,O杂环化合物之一,存在于天然产物以及具有生物活性的分子中。其作为γ-分泌酶调节剂,可用于治疗阿尔茨海默病。((a)J.Org.Chem.2017,82,2957-2964.(b)J.Med.Chem.2001,44,619.)
同时,有文献报道了噁二嗪衍生物在农药和植物生长调节方面有着重要的作用。(Chemistry Of Heterocyclic Compounds.2017,53(5),495–497.)
鉴于含噁二嗪衍生物的广泛的生物活性和应用价值,发展一种实用有效地合成多取代噁二嗪衍生物的新方法具有重要意义。
近年来,制备多取代噁二嗪衍生物的方法有:
1)2006年,Cho课题组发展了一种从肟出发,以三氟甲磺酸钪做催化剂,经过两步合成了1,2,4-噁二嗪类化合物。(Tetrahedron Letters.2006,47,9029–9033.)
2)2017年,Matthew G.Bursavich课题组发展了一种从酰胺出发,经过多步反应,得到了噁二嗪衍生物。(J.Med.Chem.2017,60,2383-2400.)
制备多取代噁二嗪衍生物的上述方法,具有一定的缺点:1)需要多步反应,最终产率低;2)使用一些金属催化剂;3)反应时间长。
发明内容
为了克服上述现有技术的不足,作为对现噁二嗪衍生物合成方法的补充,本发明提供了一种多取代噁二嗪衍生物的制备方法。
一种多取代噁二嗪衍生物的制备方法,所述化合物具有式Ⅰ所示的结构:
R1取代基团选自氟、氯、溴、碘、酯基、苯基;R2取代基团选自氟、氯、溴;其特征在于,向反应器中,加入取代苄胺肟和取代苯乙炔基碘鎓盐和碱,在溶剂中搅拌反应完毕后,使用旋转蒸发仪浓缩得到粗产物,粗产物使用硅胶柱层析分离得到目标产物,其化学过程见反应式Ⅱ:
所述的取代苄胺肟、取代苯乙炔基高碘化合物和氢氧化钾的摩尔比值为1:1.2:1.5。所述溶剂为四氢呋喃,反应温度为室温,反应时间为4h。
本发明的有益效果为:本发明提供的多取代噁二嗪衍生物的合成方法科学合理,提供了一种新的途径,通过本方法得到了具有多种取代基的产物,其特点为:原料易得、操作简单、反应条件温和、反应时间短等特点。
附图说明
图1为实施例1制备的化合物3aa的NMR图谱;
图2为实施例4制备的化合物3da的NMR图谱;
图3为实施例7制备的化合物3ac的NMR图谱。
具体实施方式
下面结合附图和具体的实施例对本发明进一步详细的说明:
下述实施例中所述试验方法,如无特殊说明,均为常规方法;所述试剂和材料,如无特殊说明,均可从商业途径获得。
实施例1
1)噁二嗪衍生物3aa的制备
10mL圆底烧瓶中加入苄胺肟1a(0.3mmol,40.8mg)、2a(0.36mmol,125.3mg)和KOH(0.45mmol,25.2mg)。加入四氢呋喃(3mL),在室温下搅拌,反应4小时。反应完毕后,使用旋转蒸发仪除去溶剂得到粗产物,粗产物经柱层析分离(200-300目硅胶)(石油醚/乙酸乙酯=3/1),使用旋转蒸发仪除去溶剂,得到目标产物3aa,其收率为77%。
谱图解析数据3aa:
1H NMR(500MHz,DMSO-d6)δ8.00(s,1H),7.86(d,1H),7.81(d,J=6.4Hz,2H),7.75(d,J=6.9Hz,2H),7.56–7.43(m,5H),7.39(d,J=7.2Hz,2H),7.30–7.20(m,4H),7.18–7.09(m,3H),6.97(d,J=7.2Hz,2H),4.42–4.32(m,1H),3.58(d,J=12.9Hz,1H).13C NMR(125MHz,DMSO-d6)δ152.97,142.25,135.11,134.18,133.34,132.02,130.95,130.15,129.00,128.57,128.24,128.01,127.48,127.09,126.84,125.83,124.57,116.24,101.13,44.41.HRMS(ESI)m/z calcd for C30H25N4O2 +(M+H)+473.1978,found 473.1974.
实施例2
用1b代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3ba:
1H NMR(500MHz,DMSO-d6)δ8.03(d,J=5.1Hz,1H),7.84(dd,J=8.5,5.5Hz,2H),7.76–7.71(m,3H),7.50(dd,J=8.5,5.7Hz,2H),7.36(dt,J=19.5,8.2Hz,4H),7.25–7.15(m,4H),7.05(dt,J=12.6,8.3Hz,4H),4.40(dd,J=13.1,5.8Hz,1H),3.58(d,J=13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ152.07,135.10,134.10,130.32,129.66,129.17,129.12,129.02,128.38,128.12,125.88,125.59,124.59,116.03(d,J=15.5Hz),115.80,115.23(d,J=21.0Hz),44.16.HRMS(ESI)m/z calcd for C30H23F2N4O2 +(M+H)+509.1789,found509.1789.
实施例3
用1c代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3ca:
1H NMR(500MHz,DMSO-d6)δ8.05(d,J=4.9Hz,1H),7.77(d,J=8.4Hz,2H),7.71(d,J=7.7Hz,2H),7.67(s,1H),7.58–7.49(m,4H),7.37(t,J=7.6Hz,2H),7.28(d,J=8.4Hz,2H),7.23(t,J=7.3Hz,4H),7.07(t,J=7.7Hz,2H),4.41(dd,1H),3.57(d,J=13.1Hz,1H).13C NMR(125MHz,DMSO-d6)δ151.86,141.34,135.64,135.32,133.98,133.65,133.16,130.66,130.41,129.01,128.45,128.37,128.20,127.79,127.22,125.94,124.60,116.24,101.51,44.08.HRMS(ESI)m/z calcd for C30H23Cl2N4O2 +(M+H)+541.1198,found 541.1196.
实施例4
用1d代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3da:
1H NMR(500MHz,DMSO-d6)δ8.09(d,J=5.3Hz,1H),7.74–7.68(m,6H),7.66(s,1H),7.47(d,J=8.6Hz,2H),7.43(d,J=8.6Hz,2H),7.38(t,J=7.7Hz,2H),7.27–7.22(m,4H),7.09(t,J=7.8Hz,2H),4.43(dd,J=13.2,5.9Hz,1H),3.58(d,J=13.1Hz,1H).13C NMR(125MHz,DMSO-d6)δ151.92,141.42,135.38,133.87(d,J=27.6Hz),131.86,131.15(d,J=32.3Hz),130.42,129.13(d,J=29.9Hz),128.42(d,J=52.4Hz),127.22,125.96,124.51(d,J=23.2Hz),121.87,116.22,101.58,44.11.HRMS(ESI)m/z calcd for C30H23Br2N4O2 +(M+H)+629.0188,found 629.0182.
实施例5
用1e代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3ea:
1H NMR(500MHz,DMSO-d6)δ8.04(d,J=5.1Hz,1H),7.86(d,J=8.5Hz,2H),7.73–7.68(m,2H),7.64–7.58(m,3H),7.52(d,J=8.5Hz,2H),7.40–7.32(m,4H),7.29–7.22(m,4H),7.13–7.07(m,2H),4.41(dd,J=13.3,5.9Hz,1H),3.56(d,J=12.7Hz,1H).13C NMR(125MHz,DMSO-d6)δ152.14,141.66,137.76,137.19,135.41,134.03,133.90,131.39,130.47,129.27,129.07,128.57,128.52,128.29,127.28,126.03,124.65,116.26,101.65,98.12,95.09,44.17.HRMS(ESI)m/z calcd for C30H23F2N4O2 +(M+H)+724.9910,found724.9909.
实施例6
用2b代替实例1中的2a,其他条件同实例1,实验结果见表1。
谱图解析数据3ab:
1H NMR(500MHz,DMSO-d6)δ8.03(d,J=5.3Hz,1H),7.87(s,1H),7.86–7.79(m,4H),7.56–7.49(m,3H),7.44(dd,J=6.5,2.9Hz,2H),7.31–7.27(m,3H),7.21(t,J=8.8Hz,2H),7.12(dd,J=8.7,5.4Hz,2H),6.75(t,J=8.8Hz,2H),4.42(dd,J=13.1,5.9Hz,1H),3.60(d,J=13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ163.10(d,J=246.5Hz),161.59(d,J=242.4Hz),153.03,142.30,134.36,131.98,130.99,130.72,129.50,128.97,128.84,128.69,128.22,127.43,126.91,126.56,116.25,115.82(d,J=21.3Hz),114.81(d,J=21.5Hz),100.75,44.05.HRMS(ESI)m/z calcd for C30H23F2N4O2 +(M+H)+509.1789,found509.1784.
实施例7
用2c代替实例1中的2a,其他条件同实例1,实验结果见表1。
谱图解析数据3ac:
1H NMR(500MHz,DMSO-d6)δ8.04(d,J=5.3Hz,1H),7.92(s,1H),7.85–7.78(m,4H),7.56–7.49(m,3H),7.45–7.37(m,4H),7.29(t,J=6.2Hz,3H),7.05(d,J=8.6Hz,2H),6.95(d,J=8.5Hz,2H),4.40(dd,J=13.1,5.8Hz,1H),3.58(d,J=13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ153.13,142.52,135.17,134.08,133.05,131.98,131.41,131.02,128.98,128.80,128.73,128.18,127.94,127.69,127.51,126.94,126.36,116.88,100.83,43.87.HRMS(ESI)m/z calcd for C30H23Cl2N4O2 +(M+H)+541.1198,found 541.1196.
实施例8
用2d代替实例1中的2a,其他条件同实例1,实验结果见表1。
谱图解析数据3ad:
1H NMR(500MHz,DMSO-d6)δ8.05(d,J=5.3Hz,1H),7.93(s,1H),7.85–7.81(m,2H),7.74(d,J=8.4Hz,2H),7.53(ddd,J=19.6,10.5,5.2Hz,5H),7.41–7.37(m,2H),7.30(q,J=6.8,6.1Hz,3H),4.39(dd,J=13.1,5.8Hz,1H),3.59(d,J=13.1Hz,1H).13C NMR(125MHz,DMSO-d6)δ153.15,142.58,134.13,133.44,132.44,131.95,131.88,131.00,130.88,128.96,128.80,128.76,128.17,127.90,127.54,126.92,126.70,124.03,119.88,116.89,100.96,43.87.HRMS(ESI)m/z calcd for C30H23Br2N4O2 +(M+H)+629.0188,found 629.0181.
实施例9
用1f代替实例6中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3fb:
1H NMR(500MHz,DMSO-d6)δ8.21(d,J=5.3Hz,1H),8.01(d,J=8.3Hz,2H),7.87(d,J=8.3Hz,2H),7.84–7.75(m,4H),7.70–7.64(m,3H),7.29(dd,J=8.5,5.5Hz,2H),7.20(t,J=8.8Hz,2H),6.87(t,J=8.7Hz,2H),4.49(dd,J=13.2,5.8Hz,1H),3.88(s,3H),3.83(s,3H),3.57(d,J=13.0Hz,1H).13C NMR(125MHz,DMSO-d6)δ166.14,163.27(d,J=247.9Hz),161.74(d,J=243.5Hz),151.83,141.42,135.97,135.04,132.97,131.54,130.39,129.99,129.52,129.17(d,J=21.0Hz),128.55,128.48,127.29,126.94,126.72,126.65,116.55,115.84(d,J=21.4Hz),115.18(d,J=21.8Hz),101.45,52.73,52.47,43.86.HRMS(ESI)m/zcalcd for C34H26F2N4NaO2 +(M+Na)+647.1718,found 647.1716.
实施例10
用1g代替实例6中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3gb:
1H NMR(500MHz,DMSO-d6)δ8.12(d,J=5.8Hz,1H),7.91(d,J=8.0Hz,2H),7.85–7.77(m,5H),7.69(dd,J=21.6,7.6Hz,4H),7.60(t,J=6.0Hz,4H),7.49(q,J=8.1Hz,4H),7.40(dt,J=14.1,7.3Hz,2H),7.29–7.21(m,4H),6.81(t,J=8.6Hz,2H),4.48(dd,J=13.2,5.8Hz,1H),3.64(d,J=12.9Hz,1H).13C NMR(125MHz,DMSO-d6)δ163.17(d,J=247.2Hz),161.63(d,J=243.3Hz),152.57,142.52,142.15,140.28,140.02,139.65,134.51,130.86,130.72,129.91,129.41,128.45,128.35,128.04,127.95,127.35,127.18,127.09,127.00,126.60,126.51,116.23,115.84(d,J=21.4Hz),114.94(d,J=21.5Hz),101.09,44.08.HRMS(ESI)m/z calcd for C42H31F2N4O2 +(M+H)+661.2415,found 661.2425.
表1
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