CN110003235B - 异噁唑并琥珀酰亚胺类化合物及其合成方法 - Google Patents

异噁唑并琥珀酰亚胺类化合物及其合成方法 Download PDF

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CN110003235B
CN110003235B CN201910221219.7A CN201910221219A CN110003235B CN 110003235 B CN110003235 B CN 110003235B CN 201910221219 A CN201910221219 A CN 201910221219A CN 110003235 B CN110003235 B CN 110003235B
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许斌
朱裕萍
邹闽芬
刘秉新
谭启涛
王辉
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University of Shanghai for Science and Technology
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Abstract

本发明涉及一种异噁唑并琥珀酰亚胺类化合物的合成方法,该化合物的结构式为:
Figure 655636DEST_PATH_IMAGE002
R1=甲基、丙基、环己基、叔丁基、苯基或苄基;R2=氢、甲基、正丁基、叔丁基、苄基、苯基、环己基或对硝基苯基;本发明方法原料简单易得、采用硝酸铜作为氮氧源、1,4‑二氧六环作为溶剂、操作简单,条件温和、反应环保、产率中等到优秀,通过应用该方法可以合成新化合物,并具有潜在的药用价值,该方法在工业生产中有很好的应用前景。

Description

异噁唑并琥珀酰亚胺类化合物及其合成方法
技术领域
本发明涉及一种3-烷基取代的异噁唑并琥珀酰亚胺类化合物的合成方法。
背景技术
4,5-二氢异噁唑类化合物是一类含有相邻氮原子和氧原子的非芳香化的五元杂环化合物,其广泛存在于具有生物活性的药物中,例如:一类含有二氢异噁唑骨架的MCD抑制剂,可以用来治疗局部缺血性心脏病(见参考文献:Nadzan,A.M.etal.J.Med.Chem.2006, 49,4055);Topramezone具有很好的除草活性(见参考文献:Ehrhardt,T.et al.Pest.Manag. Sci.,2007,63,429);在一些药用价值的天然产物中也能找到4,5-二氢异噁唑的核心骨架或片段。例如:SubereamollineA是一种治疗乳房癌的潜在有效药(见参考文献:El Sayed,K. A.et al.Mar.Drugs 2012,10,2492);另外,二氢异噁唑类化合物也可以作为有机小分子配体,例如:光学纯的SPRIX极大地加速了Cu(acac)2催化下二异丙基锌与环己烯酮的不对称迈克尔加成反应,得到49%ee的迈克尔加合物(见参考文献:Sasai,H.et al.Org.Lett.1999, 1,1795)。
异噁唑并琥珀酰亚胺又称3aH-吡咯[3,4-d]异噁唑-4,6(5H,6aH)-二酮,是一类含并环结构的二氢异噁唑类化合物,具有较特殊的用途。例如,研究表明含有异噁唑并琥珀酰亚胺结构的化合物既可以作为一类蛋白酶抑制剂(见参考文献:Keller,C.E.etal.Bioorg.Med. Chem.Lett.1992,2,1571);也可以具有一定的镇痛活性(见参考文献:Perumal,P.T.et al. Bioorg.Med.Chem.Lett.2009,19,3370);在生物培养中也有一定的应用,例如:可以提高长春花细胞产生单萜类吲哚生物碱(MIAS)的能力(见参考文献:Viaud-Massuard,M.et al. Bioorg.Med.Chem.2004,12,191);另外,这类化合物还是一类非常有用的有机合成砌块,可用于构建结构更加复杂多变的其它有机化合物(见参考文献:Starova,G.L.et al. Tetrahedron Lett.2012,53,5414)。
文献中曾报道过的合成异噁唑并琥珀酰亚胺类化合物的方法主要有以下四种:
(—)Leonori等人利用羟基亚氨酸与烯烃或炔烃在可见光介导下产生氰基氧化物,用于异噁唑或者异恶唑啉的光氧化合成。该方法反应条件较为温和、产率中等到优良、底物适用性较强,其中烯烃既可以是普通的烯烃,也可以是吸电子的烯烃,当烯烃为取代马来酰亚胺类烯烃时,反应产物为相应的取代异噁唑并琥珀酰亚胺类化合物(见参考文献:Leonori,D.et al.Chem.Commun.,2016,52,12302)。反应方程式如下:
Figure GDA0003318409980000021
(二)Takeda等人利用肟与烯烃或炔烃在叔丁基次碘酸盐等的作用下可以发生[3+2] 环加成反应得到异噁唑或四氢异噁唑类化合物,当烯烃为取代马来酰亚胺类物质时可得到相应的异噁唑并琥珀酰亚胺类化合物。该反应条件温和、产率中等到优秀(见参考文献: Takeda,Y.et al.Org.Lett.2011,13,2966)。反应方程式如下:
Figure GDA0003318409980000022
(三)Perrior等人在强酸性条件下利用1,3-二羰基类化合物与硝酸反应形成α-硝基酮中间体,该中间体可与氮甲基马来酰亚胺发生进一步的关环反应得到3-羰基取代的异噁唑并琥珀酰亚胺类化合物(见参考文献:Perrior,T.R.et al.Synth.Commun.1996,26,3401)。反应方程式如下:
Figure GDA0003318409980000023
(四)Shimizu等人从硝基化合物出发,在TsOH催化下与烯烃反应可得到相应的异噁唑类化合物,其中R1可以为烷基、芳基、酯基、羰基等。当烯烃为取代马来酰亚胺类物质时,反应可得到异噁唑并琥珀酰亚胺类化合物(见参考文献:Shimizu,T.et al.Bull.Chem.Soc.Jpn.1984,57,2531)。但该合成方法存在原料不易获得等问题。反应方程式如下:
Figure GDA0003318409980000024
(五)Xu等人从廉价易得的硝酸铜出发,通过新颖的碳-碳双键断裂反应,发展了一种烯吖内酯和简单烯烃参与的新型[2+2+1]环加成反应模式,高效合成了一系列3-芳基取代的异噁唑并琥珀酰亚胺类化合物(见参考文献:Xu,B.et al.Org.Biomol.Chem.,2019,17, 5509)。但该方法只能用于合成3-芳基取代的异噁唑并琥珀酰亚胺类化合物,而不能用于合成3-烷基取代的化合物。反应方程式如下:
Figure GDA0003318409980000031
综上所述,异噁唑并琥珀酰亚胺类化合物的合成方法有以上五种,在这些反应中,有些底物比较复杂,往往要通过几步反应得到,原料的制备比较昂贵;或者反应条件比较苛刻、复杂、不易推广、反应成本较高。
发明内容
本发明的目的在于提供一种3-烷基取代的异噁唑并琥珀酰亚胺类化合物的合成方法。
为达到上述目的,本发明方法采用的反应机理为:
Figure GDA0003318409980000032
R1=甲基、丙基、环己基、叔丁基、苯基或苄基。
R2=氢、甲基、正丁基、叔丁基、苄基、环己基、苯基或对硝基苯基。
根据上述反应机理,本发明采用了如下的技术方案:
一种制备3-烷基取代的异噁唑并琥珀酰亚胺类化合物的方法,其特征在于该方法具有如下步骤:在氮气气氛下,将原料α-酮酸、烯烃、三水合硝酸铜按1.0:1.5~3.0:1.5~3.0的摩尔比加入到1,4-二氧六环溶剂中,于75℃下搅拌反应至原料消失。反应体系除去溶剂后所得粗产物直接用柱层析进行分离提纯,得到异噁唑并琥珀酰亚胺类化合物。
本发明方法原料简单易得,采用硝酸铜作为氮氧源,1,4-二氧六环作为溶剂,操作简单,条件温和,反应环保,产率中等到优秀,在工业生产中有很好的发展前景。
具体实施方式
实施例一:3,5-二甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮 3,5-二甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在1000毫升反应三颈烧瓶中加入15.3克2-酮丁酸(150mol),33.4克N-甲基马来酰亚胺(300mol), 72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V): 乙酸乙酯(V)=2:1)进行分离提纯,得到17.2克3,5-二甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(102mol),其结构式为:
Figure GDA0003318409980000041
产率为68%。熔点: 128.0-128.7℃。
IR(KBr,cm-1):3745,2998,2967,1784,1709,1439,1387,1289,1139,982,851.
1H NMR(CDCl3,500MHz):δ5.32(d,J=9.4Hz,1H),4.25(d,J=9.4Hz,1H),3.02(s,3H), 2.15(d,J=0.95Hz,3H);.
13C NMR(CDCl3,125MHz):δ172.57,171.09,151.38,79.01,58.10,25.54,11.92.
MS(EI):m/z 168[M]+ .
HRMS(EI)m/z:calcd for C7H8N2O3[M]+168.0535,found 168.0536.
实施例二:5-正丁基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮
5-丁基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在1000 毫升反应三颈烧瓶中加入15.3克2-酮丁酸(150mol),45.9克N-正丁基马来酰亚胺(300 mol),72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V):乙酸乙酯(V)=5:1)进行分离提纯,得到21.2克5-丁基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(108mol),其结构式为:
Figure GDA0003318409980000042
无色液体,产率为72%。
IR(KBr,cm-1):3846,3741,3680,2965,1711,1551,1363.
1H NMR(CDCl3,500MHz):δ5.30(d,J=9.4Hz,1H),4.22(dd,J=0.85,9.4Hz,1H),3.56-3.47(m,2H),2.14(d,J=1.0Hz,3H),1.56-1.50(m,2H),1.31-1.24(m,2H),0.91(t,J= 7.3,3H).
13C NMR(CDCl3,125MHz):δ172.57,171.15,151.50,78.94,57.99,39.39,29.57,20.00, 13.63,11.88.
MS(ESI):m/z 211.1[M+H]+ .
HRMS(DART)m/z:calcd for C10H15O3N2[M+H]+211.1017,found 211.1017.
实施例三:5-苄基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮
5-苄基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在1000 毫升反应三颈烧瓶中加入15.3克2-酮丁酸(150mol),56.2克N-苄基马来酰亚胺(300mol), 72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V): 乙酸乙酯(V)=2:1)进行分离提纯,得到25.7克5-苄基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(96mol),其结构式为:
Figure GDA0003318409980000051
产率为64%。
熔点:136.4-136.9℃。
IR(KBr,cm-1):3473,2965,1713,1437,1395,1348,1175,888,750,701,618.
1H NMR(d6-DMSO,500MHz):δ7.34-7.28(m,5H),5.28(d,J=9.4Hz,1H),4.65(s,2H), 4.22(dd,J=9.2,0.5Hz,1H),2.12(d,J=0.65Hz,3H).
13C NMR(d6-DMSO,125MHz):δ172.20,170.78,151.39,134.76,128.97,128.87,128.51, 79.01,58.07,43.14,11.86.
MS(ESI):m/z 245.1[M+H]+ .
HRMS(DART)m/z:calcd for C13H13O3N2[M+H]+245.0921found 245.0921.
实施例四:5-环己基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮
5-环己基-3-甲基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在1000 毫升反应三颈烧瓶中加入15.3克2-酮丁酸(150mol),53.5克N-环己基马来酰亚胺(300 mol),72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V):乙酸乙酯(V)=2:1)进行分离提纯,得到24.9克5-环己基-3-甲基-3aH- 吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(99mol),其结构式为:
Figure GDA0003318409980000052
产率为 66%。熔点:145.5-146.3℃。
IR(KBr,cm-1):2931,2855,1706,1388,1196,856.
1H NMR(CDCl3,500MHz):δ5.24(d,J=9.45Hz,1H),4.16(dd,J=9.4,0.86Hz,1H),3.95 (tt,J=12.4,3.9Hz,1H),2.14(d,J=0.8Hz,3H),2.11-2.03(m,2H),1.84-1.82(m,2H), 1.67-1.65(m,1H),1.58-1.56(m,3H),1.35-1.16(m,3H).
13C NMR(CDCl3,125MHz):δ172.66,171.17,151.64,78.63,57.70,52.70,28.77,28.68, 25.80,25.78,24.96,11.87.
MS(ESI):m/z 237.1[M+H]+ .
HRMS(DART)m/z:calcd for C12H17O3N2[M+H]+237.1234found 237.1234.
实施例五:3-甲基-5-(4-硝基苯基)-3aH吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮
3-甲基-5-(4-硝基苯基)-3aH吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在 1000毫升反应三颈烧瓶中加入15.3克2-酮丁酸(150mol),65.5克N-(4-硝基苯)马来酰亚胺(300mol),72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V):乙酸乙酯(V)=2:1)进行分离提纯,得到26.5克3-甲基-5-(4-硝基苯基)-3aH吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(98mol),其结构式为:
Figure GDA0003318409980000061
产率为65%。熔点:187.1-188.4℃。
IR(KBr,cm-1):3742,2987,1727,1525,1348,1181,842,747.
1H NMR(CDCl3,500MHz):δ8.36(d,J=9.1Hz,2H),7.60(d,J=9.1Hz,2H),5.51(d,J= 9.6Hz,1H),4.47(dd,J=0.85Hz,9.7Hz,1H),2.23(d,J=0.8Hz,3H).
13C NMR(CDCl3,125MHz):δ170.67,169.27,151.19,147.56,136.32,126.86,124.73,78.87, 58.11,12.00.
MS(ESI):m/z[M+H]+ .
HRMS(DART)m/z:calcd for C12H10N3O5[M+H]+276.0615,found 276.0615.
实施例六:5-苯基-3-丙基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮
5-苯基-3-丙基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在1000 毫升反应三颈烧瓶中分别加入20.0克2-氧代己酸(150mol),52.0克N-苯基马来酰亚胺(300 mol),72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V):乙酸乙酯(V)=5:1)进行分离提纯,得到24.1克5-苯基-3-丙基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(92mol),其结构式为:
Figure GDA0003318409980000062
产率为61%。熔点:134.8-135.3℃。
IR(KBr,cm-1):2964,1720,1501,1385,1191,872,742.
1H NMR(CDCl3,500MHz):δ7.50-7.47(m,2H),7.44-7.41(m,1H),7.28-7.26(m,2H),5.45 (d,J=9.6Hz,1H),4.43(d,J=9.6Hz,1H),2.62-2.56(m,1H),2.50-2.44(m,1H),1.84-1.77(m, 1H),1.73-1.64(m,1H),1.02(t,J=7.4,3H).
13C NMR(CDCl3,125MHz):δ171.68,170.20,154.82,130.93,129.45,129.31,126.24,78.78, 57.05,28.38,19.34,13.81.
MS(ESI):m/z 259.1[M+H]+.
实施例七:3-环己基-5-苯基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮
3-环己基-5-苯基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在1000 毫升反应三颈烧瓶中分别加入25.5克3-环己基-2-氧代丙酸(150mol),52.0克N-苯基马来酰亚胺(300mol),72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V):乙酸乙酯(V)=5:1)进行分离提纯,得到24.3克3-环己基-5-苯基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(81mol),产率为54%。其结构式为:
Figure GDA0003318409980000071
熔点:178.5-178.8℃。
IR(KBr,cm-1):3063,2932,2857,1721,1500,1388,1188,869,731,690.
1H NMR(d6-DMSO,500MHz):δ7.50-7.47(m,2H),7.44-7.41(m,1H),7.29-7.27(m,2H) 5.44(d,J=9.6Hz,1H),4.52(d,J=9.6Hz,1H),2.61-2.56(m,1H),2.12-2.10(m,1H),2.00-1.97(m,1H),1.83-1.81(m,2H),1.72-1.70(m,1H),1.64-1.57(m,2H),1.42-1.24(m,4H).
13C NMR(d6-DMSO,125MHz):δ171.68,170.39,158.46,130.98,129.47,129.31,126.24, 78.81,56.00,36.38,30.86,29.51,26.00,25.89,25.59.
MS(ESI):m/z 299.1[M+H]+.
实施例八:3-苄基-5-苯基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮
3-苄基-5-苯基-3aH-吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮采用下述步骤:①在1000 毫升反应三颈烧瓶中分别加入26.7克2-氧代-4-苯基丁酸(150mol),52.0克N-苯基马来酰亚胺(300mol),72.5克三水合硝酸铜(300mol),750毫升1,4-二氧六环,加热至75℃。
用薄层层析方法跟踪反应,反应至原料消失;②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚(V):乙酸乙酯(V)=5:1)进行分离提纯,得到36.4克3-苄基-5-苯基-3aH- 吡咯并[3,4-d]异恶唑-4,6(5H,6aH)-二酮(119mol),其结构式为:
Figure GDA0003318409980000081
产率为79%。熔点:176.7-177.2℃。
IR(KBr,cm-1):2985,1727,1495,1385,1187,868,700.
1H NMR(CDCl3,500MHz):δ7.49-7.46(m,2H),7.44-7.36(m,5H),7.32-7.30(m,1H)7.23(d, J=7.6Hz,2H),5.38(d,J=9.7Hz,1H),4.29(d,J=9.6Hz,1H),4.04(d,J=14.7Hz,1H), 3.74(d,J=14.7Hz,1H).
13C NMR(CDCl3,125MHz):δ171.28,169.94,153.89,133.86,130.77,129.45,129.35,129.24, 129.10,127.65,126.09,79.06,55.64,32.28.
MS(ESI):m/z 307.1[M+H]+

Claims (1)

1.一种制备异噁唑并琥珀酰亚胺类化合物的方法,其特征在于该方法具有如下步骤:在氮气气氛下,将α-酮酸、烯烃、三水合硝酸铜按1.0:1.5~3.0:1.5~3.0的摩尔比加入到1,4-二氧六环溶剂中,于75℃下搅拌反应至原料消失;反应体系除去溶剂后,所得粗产物再用柱层析进行分离提纯,得到异噁唑并琥珀酰亚胺类化合物
Figure FDA0003318409970000011
所述的α-酮酸的结构式为:
Figure FDA0003318409970000012
所述的烯烃的结构式为:
Figure FDA0003318409970000013
其中,R1=甲基、丙基或环己基;R2=甲基、环己基或对硝基苯基。
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Visible-light-mediated generation of nitrile oxides for the photoredox synthesis of isoxazolines and isoxazoles;Thomas D. Svejstrup,等;《Chemical Communications》;20160921;第52卷(第83期);12302-12305 *

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