CN107056808B - 3-芳基取代异噁唑并琥珀酰亚胺类化合物及其合成方法 - Google Patents

3-芳基取代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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CN107056808B
CN107056808B CN201710189763.9A CN201710189763A CN107056808B CN 107056808 B CN107056808 B CN 107056808B CN 201710189763 A CN201710189763 A CN 201710189763A CN 107056808 B CN107056808 B CN 107056808B
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CN107056808A (zh
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许斌
张可
高明春
乔蔚
王叶东
沈惟嘉
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University of Shanghai for Science and Technology
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Abstract

本发明涉及一种3‑芳基取代异噁唑并琥珀酰亚胺类化合物及其合成方法，该化合物的结构式为：Ar=苯基、对甲基苯基、对溴苯基、对硝基苯基、2‑萘基；所述的烯烃的结构式为：

Description

3-芳基取代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-芳基取代异噁唑并琥珀酰亚胺类化合物及其合成方法。
背景技术
二氢异噁唑为含有相邻的一个氧杂原子和一个氮杂原子的五元杂环，这种化合物具有很多的生物活性，并且还具有很好的药理学特性。在众多药物或活性分子中都可以找到其分子骨架或片段。例如，醋酸罗昔非班含有二氢异噁唑骨架，作为血小板糖蛋白Ⅱb/Ⅲa受体抑制剂，主要用于心脑血管疾病(见参考文献：Batt,D.G.et al.J.Org.Chem.2000,65,8100)。二氢异噁唑类化合物还具有除草活性(见参考文献：Li，Z.M.etal.Heterocyclic.Commun.2008,14,397)，以及杀虫活性(见参考文献：Mita,T.etal.US8053452B2)。另外，二氢异噁唑类化合物作为有机小分子配体，在有机合成中也有着广泛的应用(见参考文献：Arai,M.A.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不仅具有镇痛活性(见参考文献：Perumal，P.T.etal.Bioorg.Med.Chem.Lett.2000,10,95)还能有效地抑制由真菌病原体引起的植物病害(见参考文献：David,D.et al.WO2008013622 A2)。此外，Stepakov等人从异噁唑并琥珀酰亚胺类化合物出发，经过两步反应得到可吡咯[2,1-a]异喹啉类结构，该骨架广泛存在天然产物中具有很多生物活性(见参考文献：Stepakov,A.V.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几种：
(一)Takeda等人利用肟与烯烃或炔烃发生[3+2]环加成反应得到异噁唑或四氢异噁唑类化合物，其中烯烃可以为普通烯烃，也可以为氮苯基马来酰亚胺或足球烯。当烯烃为氮苯基马来酰亚胺时可得到相应的3-芳基取代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)。
(二)Shimizu等人从硝基化合物出发，在酸性条件下与烯烃反应可得到相应的异噁唑类化合物，其中R可以为烷基、芳基、磺酰基、酯基或羰基。当烯烃为氮取代马来酰亚胺时，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.etal.Bull.Chem.Soc.Jpn.1984,57,2531)。
(三)Barrett课题组在酸性条件下，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：Barrett,D.et al.Synth.Commun.1996,28,3401)。
(四)Martin课题组从氰基氮氧化物与烯烃原料出发，利用1，3-偶极加成反应得到3aH-呋喃[3,4-d]异噁唑，产物可与肼反应，通过串联的开环-关环过程，得到相应的异噁唑并琥珀酰亚胺类化合物(见参考文献：Martin,M.R.et al.Tetrahedron,2001,57,4389)。
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几种，但在这些反应中，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，不易推广，反应成本较高。
发明内容
本发明的目的之一在于提供一类3-芳基取代异噁唑并琥珀酰亚胺类化合物。
本发明的目的之二在于提供该化合物的合成方法。
为达到上述目的，本发明方法采用的反应机理为：
根据上述反应机理，本发明采用了如下的技术方案：
1、一种3-芳基取代异噁唑并琥珀酰亚胺类化合物，其特征在于该化合物的结构式为：
其中Ar为：苯基、对甲基苯基、对溴苯基、对硝基苯基或2-萘基；R为：氢、苯基、正丁基或苄基。
2、一种制备根据权利要求1所述的3-芳基取代异噁唑并琥珀酰亚胺类化合物的方法，其特征在于该方法的具体步骤：将(Z)-4-芳香亚甲基-2-苯基-5(4H)-噁唑酮、烯烃、三水合硝酸铜、碘化钾按1：(1.0～3.0)：(2.0～8.0)：(1.0～3.0)的摩尔比加入到1,4-二氧六环溶剂中，于80～90℃下搅拌反应至原料消失；反应体系除去溶剂后所得粗产物，经分离提纯，得到3-芳基取代异噁唑并琥珀酰亚胺类化合物；所述的(Z)-4-芳香亚甲基-2-苯基-5(4H)-噁唑酮的结构式为：所述的烯烃的结构式为：
本发明方法原料简单易得，并采用三水合硝酸铜作为氮源和氧源，使用常规的反应溶剂，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应用前景。
具体实施方式
实施例一：3,5-二苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
3,5-二苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中加入14.9克(Z)-4-苯亚甲基-2-苯基-5(4H)-噁唑酮，10.4克N-苯基马来酰亚胺，29.0克三水合硝酸铜，10.0克碘化钾，750毫升1,4-二氧六环，加热至80℃。用薄层层析方法跟踪反应至原料消失(2h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:乙酸乙酯＝7:1)进行分离提纯，得到12.7克3,5-二苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率为73％。熔点：176-177℃。
IR(KBr,cm-1):3065,1791,1719,1595,1497,1448,1386,1199，899，749，691，621.
1H NMR(CDCl3,500MHz):δ8.06-8.01(m,2H),7.51-7.38(m,6H),7.30-7.25(m,2H),5.66(d,J＝10Hz,1H),4.97(d,J＝9.5Hz,1H).
13C NMR(CDCl3,125MHz):δ170.9,169.8,152.8,131.3,130.8,129.3,129.2,128.9,128.1,126.7,126.2,80.4,54.9.
EI-MS m/z:292[M+].
HRMS(EI)m/z:calcd for C17H12N2O3[M+]292.0848,found 292.0844.
实施例二：5-正丁基-3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
5-正丁基-3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中加入14.9克(Z)-4-苯亚甲基-2-苯基-5(4H)-噁唑酮，27.6克N-正丁基马来酰亚胺，58.0克三水合硝酸铜，20.0克碘化钾，750毫升1,4-二氧六环，加热至85℃。用薄层层析方法跟踪反应至原料消失(2h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:乙酸乙酯＝7:1)进行分离提纯，得到13.4克5-正丁基-3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率82％。熔点：82-84℃。
IR(KBr,cm-1):3065,2952,1783,1709,1444,1402,1333，899，754，686.
1H NMR(CDCl3,500MHz):δ8.02-7.92(m,2H),7.49-7.40(m,3H),5.49(d,J＝9.6Hz,1H),4.81(d,J＝9.5Hz,1H),3.55-3.43(m,2H),1.57-1.45(m,2H),1.30-1.19(m,2H),0.86(t,J＝7.3Hz,3H).
13C NMR(CDCl3,125MHz):δ172.0,170.9,152.8,131.1,128.8,128.0,126.9,80.4,54.9,39.5,29.4,19.9,13.5.
EI-MS m/z:272[M+].
HRMS(EI)m/z:calcd for C15H16N2O3[M+]272.1161,found 272.1159.
实施例三：3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中加入14.9克(Z)-4-苯亚甲基-2-苯基-5(4H)-噁唑酮，17.4克马来酰亚胺，116.0克三水合硝酸铜，30.0克碘化钾，750毫升1,4-二氧六环，加热至90℃。用薄层层析方法跟踪反应至原料消失(3h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:二氯甲烷＝3:1)进行分离提纯，得到9.1克3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率70％。熔点：220-221℃。
IR(KBr,cm-1):3198,3094,1793,1729,1563,1336,1180,892，771，690.
1H NMR(d6-DMSO,500MHz):δ11.89(s,1H),7.92-7.86(m,2H),7.53-7.45(m,3H),5.52(d,J＝9.4Hz,1H),5.15(d,J＝9.4Hz,1H).
13C NMR(d6-DMSO,125MHz):δ174.8,173.7,154.0,131.2,129.2,128.3,127.6,82.8,56.6.
EI-MS m/z:216[M+].
HRMS(EI)m/z:calcd for C11H8N2O3[M+]216.0535,found 216.0541.
实施例四：5-苯基-3-(4-溴苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
5-苯基-3-(4-溴苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中加入19.7克(Z)-4-(4-溴苯亚甲基)-2-苯基-5(4H)-噁唑酮，15.6克N-苯基马来酰亚胺，29.0克三水合硝酸铜，10.0克碘化钾，750毫升1,4-二氧六环，加热至80℃。用薄层层析方法跟踪反应至原料消失(4h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:乙酸乙酯＝7:1)进行分离提纯，得到17.9克5-苯基-3-(4-溴苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率为80％。熔点：204-206℃。
IR(KBr,cm-1):3426,2923,1722,1496,1389,1194,832，619.
1H NMR(CDCl3,500MHz):δ7.91(d,J＝5.7Hz,1H),7.59(d,J＝6.0Hz,1H),7.52-7.36(m,3H),7.32-7.20(m,2H),5.68(d,J＝9.1Hz,1H),4.93(d,J＝8.9Hz,1H).
13C NMR(CDCl3,125MHz):δ170.6,169.7,152.1,132.2,130.7,129.5,129.4,129.3,126.1,125.9,125.7,80.6,54.7.
EI-MS m/z:370[M+(79Br)],372[M+(81Br)].
HRMS(EI)m/z:calcd for C17H11BrN2O3[M+]369.9953,found 369.9955.
实施例五：3-(萘-2-基)-5-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
3-(萘-2-基)-5-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中加入18.0克(Z)-4-(萘-2-基亚甲基)-2-苯基-5(4H)-噁唑酮，15.6克N-苯基马来酰亚胺，29.0克三水合硝酸铜，10.0克碘化钾，750毫升1,4-二氧六环，加热至90℃。用薄层层析方法跟踪反应至原料消失(2h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:乙酸乙酯＝7:1)进行分离提纯，得到14.7克3-(萘-2-基)-5-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率为72％。熔点：203-204℃。
IR(KBr,cm-1):3497,3059,1794,1723,1594,1495,1379,1193,899,745.
1H NMR(CDCl3,500MHz):δ8.53(s,1H),8.08(d,J＝8.7Hz,1H),7.94(d,J＝8.7Hz,1H)，7.86(t,J＝9Hz,2H),7.60-7.36(m,5H),7.32-7.24(m,2H),5.71(d,J＝9.7Hz,1H),5.07(d,J＝9.7Hz,1H).
13C NMR(CDCl3,125MHz):δ170.8,170.0,152.9,134.4,132.8,130.9,129.6,129.3,129.2,129.0,128.8,127.9,127.8,126.9,126.2,124.2,123.8,80.6,55.0.
EI-MS m/z:342[M+].
HRMS(EI)m/z:calcd for C21H14N2O3[M+]342.1004,found 342.1001.
实施例六：5-苯基-3-(4-甲基苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
5-苯基-3-(4-甲基苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中分别加入15.8克(Z)-4-(4-甲基苯亚甲基)-2-苯基-5(4H)-噁唑酮，15.6克N-苯基马来酰亚胺，29.0克三水合硝酸铜，10.0克碘化钾，750毫升1,4-二氧六环，加热至80℃。用薄层层析方法跟踪反应至原料消失(3h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:乙酸乙酯＝7:1)进行分离提纯，得到16.5克5-苯基-3-(4-甲基苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率为90％。熔点：179℃。
IR(KBr,cm-1):3496,3054,2963,1724,1499,1385,1193,892,854,695.
1H NMR(CDCl3,500MHz):δ7.93(d,J＝8.2Hz,1H),7.50-7.39(m,3H),7.32-7.24(m,4H),5.65(d,J＝9.7Hz,1H),4.96(d,J＝9.7Hz,1H)，2.41(s,3H).
13C NMR(CDCl3,125MHz):δ171.1,170.0,152.8,141.8,130.9,129.6,129.3,129.2,128.1,126.2,123.9,80.3,55.0,21.6.
EI-MS m/z:306[M+].
HRMS(EI)m/z:calcd for C18H14N2O3[M+]306.1004,found 306.1010.
实施例七：5-苯基-3-(4-硝基苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
5-苯基-3-(4-硝基苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中分别加入17.7克(Z)-4-(4-硝基苯亚甲基)-2-苯基-5(4H)-噁唑酮，31.2克N-苯基马来酰亚胺，116.0克三水合硝酸铜，30.0克碘化钾，750毫升1,4-二氧六环，加热至90℃。用薄层层析方法跟踪反应至原料消失(4h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:二氯甲烷＝3:1)进行分离提纯，得到17.2克5-苯基-3-(4-硝基苯基)-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率为85％。熔点：251℃。
IR(KBr,cm-1):3496,3068,2956,1791,1723,1518,1386,1345,1205,910,856,744,688,624.
1H NMR(d6-DMSO,500MHz):δ8.36(d,J＝8.8Hz,2H),8.20(d,J＝8.8Hz,2H),7.40-7.52(m,3H),7.32-7.26(m,2H),5.84(d,J＝9.8Hz,1H),5.49(d,J＝9.8Hz,1H).
13C NMR(d6-DMSO,125MHz):δ172.2,171.3,153.1,149.0,133.9,132.1,129.7,129.5,129.4,127.5,124.4,82.7,55.4.
EI-MS m/z:337[M+].
HRMS(EI)m/z:calcd for C17H11N3O5[M+]337.0699,found 337.0695.
实施例八：5-苄基-3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮
5-苄丁基-3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮采用下述步骤：①在1000毫升反应釜中加入14.9克(Z)-4-苯亚甲基-2-苯基-5(4H)-噁唑酮，13.8克N-苄基马来酰亚胺，29.0克三水合硝酸铜，10.0克碘化钾，750毫升1,4-二氧六环，加热至85℃。用薄层层析方法跟踪反应至原料消失(2h)；②反应体系除去溶剂后所得粗产物直接用柱层析(石油醚:乙酸乙酯＝7:1)进行分离提纯，到13.0克5-苄基-3-苯基-3aH-吡咯[3,4-d]异噁唑-4,6(5H，6aH)-二酮，其结构式为：产率71％。熔点：161℃。
IR(KBr,cm-1):3034,2968,1781,1710,1433,1399,1339,1176,892,690.
1H NMR(CDCl3,500MHz):δ8.02-7.95(m,2H),7.51-7.41(m,3H),7.37-7.27(m,5H),5.48(d,J＝9.6Hz,1H),4.79(d,J＝9.6Hz,1H),4.66(dd,J＝39.7,14.0Hz,2H).
13C NMR(CDCl3,125MHz):δ171.5,170.6,152.7,134.6,131.2,128.9,128.8,128.4,128.0,126.8,80.5,54.9,43.3.
EI-MS m/z:306[M+].
HRMS(EI)m/z:calcd for C18H14N2O3[M+]306.1004,found 306.1006.

Claims (1)

1.一种制备3-芳基取代异噁唑并琥珀酰亚胺类化合物的方法，其特征在于该方法的具体步骤：将(Z)-4-芳香亚甲基-2-苯基-5(4H)-噁唑酮、烯烃、三水合硝酸铜、碘化钾按1：(1.0～3.0)：(2.0～8.0)：(1.0～3.0)的摩尔比加入到1,4-二氧六环溶剂中，于80～90℃下搅拌反应至原料消失；反应体系除去溶剂后所得粗产物，经分离提纯，得到3-芳基取代异噁唑并琥珀酰亚胺类化合物，3-芳基取代异噁唑并琥珀酰亚胺类化合物的结构式为：
所述的(Z)-4-芳香亚甲基-2-苯基-5(4H)-噁唑酮的结构式为：所述的烯烃的结构式为：其中Ar为：苯基、对甲基苯基、对溴苯基、对硝基苯基或2-萘基；R为：氢、苯基、正丁基或苄基。
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