CN110526853A - 3,3-二取代-2-吲哚酮衍生物及其制备方法 - Google Patents

3,3-二取代-2-吲哚酮衍生物及其制备方法 Download PDF

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CN110526853A
CN110526853A CN201810503673.7A CN201810503673A CN110526853A CN 110526853 A CN110526853 A CN 110526853A CN 201810503673 A CN201810503673 A CN 201810503673A CN 110526853 A CN110526853 A CN 110526853A
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林旭锋
阿卜杜勒·拉赫曼
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Zhejiang University ZJU
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Abstract

本发明公开的3,3‑二取代‑2‑吲哚酮衍生物是具有如下结构式的消旋体、左旋或右旋的光学活性体；

Description

3,3-二取代-2-吲哚酮衍生物及其制备方法
技术领域
本发明属于有机合成技术领域，具体涉及3,3-二取代-2-吲哚酮衍生物及其制备方法。
背景技术
2-吲哚酮衍生物是一类重要的含氮杂环化合物，也是一些药物活性分子的重要骨架，具有作为酶抑制剂、抗癌/抗肿瘤等药理活性((a)N.H.Greig,X.-F.Pei,T.T.Soncrant,D.K.Ingram and A.Brossi,Med.Res.Rev.,1995,15,3；(b)C.V.Galliford,K.A.Scheidt,Angew.Chem.,Int.Ed.,2007,46,8748.)。因此，研究合成2-吲哚酮衍生物，特别是不对称催化合成3,3-二取代-2-吲哚酮衍生物，受到了人们的关注((a)R.Dalpozzo,Org.Chem.Front.,2017,4,2063；(b)R.Dalpozzo,G.Bartoliand G.Bencivenni,Chem.Soc.Rev.,2012,41,7247；(c)Z.-Y.Cao and J.Zhou,Org.Chem.Front.,2015,2,849；(d)D.Cheng,Y.Ishihara,B.Tan and C.F.Barbas III,ACS Catal.,2014,4,743；(e)L.Hong and R.Wang,Adv.Synth.Catal.,2013,355,1023；(f)R.Rios,Chem.Soc.Rev.,2012,41,1060；(g)G.S.Singh and Z.Y.Desta,Chem.Rev.,2012,112,6104；(h)N.R.Ball-Jones,J.J.Badille and A.K.Franz,Org.Biomol.Chem.,2012,10,5165)。另外吡咯与吲哚及其衍生物也具有重要的药理活性(Chem.Rev.,2006,106,2875；Angew.Chem.,Int.Ed.,2009,48,9608；Chem.Rev.2004,104,2481；Tetrahedron,2006,62,7213)。醌甲基化物类化合物经常出现在天然产物，同时作为合成子用于有机合成((a)B.T.Ramanjaneyulu,S.Mahesh and R.V.Anand,Org.Lett.,2015,17,3952；(b)V.Reddy and R.V.Anand,Org.Lett.,2015,17,3390；(c)A.Lopez,A.Parra,C.Jarava-Barrera and M.Tortosa,Chem.Commun.,2015,51,17684；(d)Z.Wang and J.Sun,Synthesis,2015,47,3629.；(e)X.Zhang,Y.-H.Chen and B.Tan,Tetrahedron Lett.,2018,59,473；(f)Y.Shen,J.Qi,Z.Mao and S.Cui,Org.Lett.,2016,18,2722.(g)A.Parra and M.Tortosa,Chem-CatChem,2015,7,1524；)。那么可以预期若组装成含有2-吲哚酮衍生物，醌甲基化物和吡咯基或吲哚基等高药理活性结构的3,3-二取代-2-吲哚酮衍生物的分子将具有较高生物活性。
发明内容
本发明的目的是提供一种3,3-二取代-2-吲哚酮衍生物及其制备方法。
一种3,3-二取代-2-吲哚酮衍生物,它是具有如下结构式的消旋体、左旋或右旋的光学活性体；
式中：R1和R6选自H、三氟甲基、二氟甲基、苄基、烯丙基、C1～C4烷基，R2～R5和R7～R11选自H、卤素、硝基、三氟甲基、二氟甲基、环丙基、环丁基、环戊基、环己基、苄氧基、苯氧基、苄基、C1～C4烷基或C1～C4烷氧基。
所述的3,3-二取代-2-吲哚酮衍生物的制备方法，是以靛红衍生的醌甲基化物类化合物为原料，跟如吡咯类化合物或吲哚类化合物等亲核试剂反应，以螺环磷酸为催化剂，在有机溶剂中于10～80℃，反应12～48小时，纯化得到3,3-二取代-2-吲哚酮衍生物，所述的靛红衍生的醌甲基化物类化合物和亲核试剂的摩尔比为1：1～1.2，螺环磷酸催化剂和靛红衍生的醌甲基化物类化合物的摩尔比为5～20：100。
所述的螺环磷酸催化剂为具有结构式(1)的化合物，可以是消旋体、左旋或右旋的光学活性体：
式中：R选自H、烷基、芳基或取代的芳基、9-蒽基、菲基，取代的芳基上的取代基可以是一个或多个，包括卤素、硝基、三氟甲基、二氟甲基、环丙基、环丁基、环戊基、环己基、苄氧基、苯氧基、苄基、苯基、C1～C4烷基或C1～C4烷氧基。
所述的靛红衍生的醌甲基化物类化合物结构如下式(2)所示：
所述的亲核试剂为吡咯类化合物或吲哚类化合物，结构如下式(3)和式(4)所示：
式中：R1～R11如权利要求1所述。
所述的有机溶剂为甲苯、二甲苯、苯、二氯甲烷、氯仿、1,2-二氯乙烷、氟苯、氯苯或乙基苯。
与现有技术相比，本发明具有以下优点：
1)无需金属催化，反应可在温和条件下进行；
2)含有取代基的吡咯或吲哚能直接作为反应底物，其来源十分广泛，这些降低了最终产品的制备成本；
3)可以获得高光学活性的含吲哚基和苯酚基的3,3-二取代-2-吲哚酮衍生物。
综上所述，本发明利用催化1，6加成反应方法合成3,3-二取代-2-吲哚酮衍生物，反应条件温和，工艺简单，操作便捷，所得产物有潜在的良好的生物活性，这将对新药筛选有重要意义。
具体实施方式
以下实施例将有助于理解本发明，但不限于本发明的内容。
靛红衍生的醌甲基化物类化合物可以按照文献H.Wang,K.Wang,Y.Man,X.Gao,L.Yang,Y.Ren,Na Li,B.Tang and G.Zhao,Adv.Synth.Catal.,2017,359,3934公开的方法制备。
实施例1
反应瓶中依次加入1a(0.05mmol)和吲哚2a(0.06mmol)，和二氯甲烷(1mL)，最后加入螺环磷酸催化剂(S)-4a(0.0075mmol)；10度搅拌反应48小时，反应完毕，直接柱层析纯化得到手性的3,3-二取代-2-吲哚酮衍生物3a，产率85％；产物表征如下：5-Bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3,3'-biindolin-2-one(3a)85％yield；91％ee,determined by HPLC[Daicel Chiralcel OD-H column(250×4.6mm),n-hexane/i-PrOH＝80/20,0.8mL/min,254nm；tminor＝5.644min,tmajor＝10.951min；[α]D 20＝67(c 0.2,CH2Cl2)；1H NMR(400MHz,DMSO)δ11.02(d,J＝2.0Hz,1H),10.76(s,1H),7.43(dd,J＝8.3,2.0Hz,1H),7.37(d,J＝8.2Hz,1H),7.20(d,J＝1.9Hz,1H),7.13(s,2H),7.07–7.00(m,2H),6.96(d,J＝8.3Hz,1H),6.88(d,J＝7.9Hz,1H),6.86–6.78(m,2H),1.28(s,18H)；13C NMR(101MHz,DMSO)δ178.67,152.93,140.63,138.62,137.07,136.78,130.64,130.09,127.79,125.33,24.84,123.96,121.16,119.81,118.46,115.01,113.10,111.75,57.14,34.60,30.21；IR(film):γ＝3404,2983,2356,2215,2155,1677,1472,1359,1251,1026,905,826,764cm-1；HRMS(EI-TOF):calcd for C30H31BrN2O3 530.1569,found530.1572.
按照上述一样的反应过程，改变反应底物，可以得到以下3,3-二取代-2-吲哚酮衍生物：
5-Bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-4'-methyl-3,3'-biindolin-2-one(3b)86％yield；90％ee,determined by HPLC[Daicel Chiralcel OD-Hcolumn(250×4.6mm),n-hexane/i-PrOH＝80/20,0.8mL/min,254nm；tminor＝5.838min,tmajor＝10.888min；[α]D 20＝88.1(c 0.5,CH2Cl2)；1H NMR(400MHz,DMSO)δ10.99(d,J＝1.9Hz,1H),10.69(s,1H),7.44(dd,J＝8.2,1.8Hz,1H),7.22(d,J＝8.0Hz,1H),7.08(d,J＝15.5Hz,2H),6.94(t,J＝7.9Hz,3H),6.63(d,J＝7.1Hz,1H),6.45(s,1H),1.86(s,3H),1.30(s,18H)；13C NMR(101MHz,DMSO)δ152.97,140.43,138.50,137.91,130.66,127.98,124.39,121.32,121.17,112.97,111.92,109.69,57.95,34.63,30.21；IR(film):γ＝3421,2924,2256,2215,1655,1472,1379,1051,1026,1005,826,764cm-1；HRMS(EI-TOF):calcd forC31H33BrN2O2 544.1725,found 544.1721.
5-Chloro-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-6'-fluoro-3,3'-biindolin-2-one(3g)83％yield；97％ee,determined by HPLC[Daicel Chiralcel OD-Hcolumn(250×4.6mm),n-hexane/i-PrOH＝80/20,0.8mL/min,254nm；tminor＝5.363min,tmajor＝7.898min；[α]D 20＝107.1(c0.7,CH2Cl2)；1H NMR(400MHz,DMSO)δ11.08(d,J＝2.1Hz,1H),10.77(s,1H),7.30(dd,J＝8.3,2.2Hz,1H),7.15(dd,J＝10.0,2.3Hz,1H),7.10(d,J＝2.3Hz,3H),7.01(d,J＝8.3Hz,2H),6.90(dd,J＝8.8,5.6Hz,1H),6.83(d,J＝2.5Hz,1H),6.77–6.68(m,1H),1.27(s,18H)；13C NMR(101MHz,DMSO)δ178.68,159.79,157.46,152.95,140.19,138.70,136.83(m,J F-C＝121.67),136.53,130.19,127.90,125.55,125.49,124.98,123.84,122.19,115.05,111.27,97.71,97.46,57.20,34.57,30.20；19FNMR(376MHz,DMSO)δ-121.74(td,J＝9.9,5.6Hz)；IR(film):γ＝3439,2253,2127,1910,1657,1472,1053,1026,1007,825,763,627cm-1；HRMS(EI-TOF):calcd forC30H30FClN2O2504.1980,found 504.1984.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-6'-fluoro-5-methyl-3,3'-biindolin-2-one(3m)80％yield；96％ee,determined by HPLC[Daicel Chiralcel OD-Hcolumn(250×4.6mm),n-hexane/i-PrOH＝80/20,0.8mL/min,254nm；tminor＝5.208min,tmajor＝7.243min；[α]D 20＝67(c 0.7,CH2Cl2)；1H NMR(400MHz,DMSO)δ11.03(d,J＝1.7Hz,1H),10.53(s,1H),7.20–7.12(m,3H),7.04(d,J＝7.8Hz,1H),6.97(s,2H),6.95–6.91(m,1H),6.89(d,J＝7.8Hz,1H),6.80(d,J＝2.4Hz,1H),6.72(td,J＝9.6,2.3Hz,1H),2.22(s,3H),1.30(s,18H)；13C NMR(101MHz,DMSO)δ179.06,159.75,157.42,152.67,138.80,138.48,136.80(m,J F-C＝121.67),134.60,131.06,130.29,128.14,125.77,125.38,125.35,124.00,122.46,116.04,109.42,97.54,97.29,57.00,34.57,30.27,20.73；IR(film):γ＝3425,2942,2924,2834,2254,1652,1458,1190,1051,1026,1006,825,763,629cm-1；HRMS(EI-TOF):calcd for C31H33FN2O2 484.2526,found 484.2530.
实施例2
反应瓶中依次加入1a(0.05mmol)和吲哚2a(0.05mmol)，和1，2-二氯乙烷(2mL)，最后加入消旋体螺环磷酸催化剂4b(0.005mmol)；80度搅拌反应12小时，反应完毕，直接柱层析纯化得到消旋体的3,3-二取代-2-吲哚酮衍生物3a，产率92％.
按照上述一样的反应过程，改变反应底物，可以得到以下3,3-二取代-2-吲哚酮衍生物：
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1’-methyl-3,3'-biindolin-2-one(3t)89％yield；1H NMR(400MHz,CDCl3)δ8.07(s,1H),7.29(q,J＝7.9Hz,3H),7.25(d,J＝1.3Hz,1H),7.22–7.16(m,1H),7.15–7.05(m,1H),7.02(t,J＝7.2Hz,1H),6.94(dd,J＝7.6,4.2Hz,2H),6.91–6.84(m,1H),6.80(d,J＝2.5Hz,1H),5.14(s,1H),3.32(s,3H),1.32(s,18H)；13C NMR(101MHz,CDCl3)δ178.27,152.96,143.07,136.92,135.26,134.24,130.16,127.92,125.93,125.64,124.93,124.37,124.15,122.52,121.96,120.88,120.71,119.78,119.45,117.50,111.15,108.17,102.59,57.13,34.45,30.28,26.64；IR(film):γ＝3637,3301,2956,2920,1706,1619,1471,1321,1237,1143,1122,1055,909,803,750cm-1；HRMS(EI-TOF):calcd for C31H34N2O2 466.2620,found 466.2617.
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-methyl-3,3'-biindolin-2-one(3s)88％yield；1H NMR(400MHz,CDCl3)δ8.07(s,1H),7.29(q,J＝7.9Hz,3H),7.25(d,J＝1.3Hz,1H),7.22–7.16(m,1H),7.15–7.05(m,1H),7.02(t,J＝7.2Hz,1H),6.94(dd,J＝7.6,4.2Hz,2H),6.91–6.84(m,1H),6.80(d,J＝2.5Hz,1H),5.14(s,1H),3.32(s,3H),1.32(s,18H)；13C NMR(101MHz,CDCl3)δ178.27,152.96,143.07,136.92,135.26,134.24,130.16,127.92,125.93,125.64,124.93,124.37,124.15,122.52,121.96,120.88,120.71,119.78,119.45,117.50,111.15,108.17,102.59,57.13,34.45,30.28,26.64；IR(film):γ＝3637,3301,2956,2925,1706,1619,1471,1436,1321,1237,1143,1122,1055,909,803,750,668cm-1；HRMS(EI-TOF):calcd for C31H34N2O2 466.2620,found 466.2617.
实施例3
反应瓶中依次加入1a(0.05mmol)和吡咯5a(0.06mmol)，和二氯甲烷(1mL)，最后加入螺环磷酸催化剂(S)-4a(0.0075mmol)；10度搅拌反应48小时，反应完毕，直接柱层析纯化得到手性的3,3-二取代-2-吲哚酮衍生物6，产物表征如下：
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-(1H-pyrrol-2-yl)indolin-2-one(6)70％yield；84％ee,determined by HPLC[Daicel Chiralcel OD-H column(250×4.6mm),n-hexane/i-PrOH＝80/20,0.8mL/min,254nm；tminor＝5.12min,tmajor＝10.143min；[α]D 20＝68(c 0.5,CH2Cl2)；1H NMR(400MHz,DMSO)δ10.56(s,2H),7.39(d,J＝7.4Hz,1H),7.21(td,J＝7.7,1.1Hz,1H),7.00(td,J＝7.6,0.8 Hz,1H),6.95–6.89(m,2H),6.82(s,2H),6.68(dd,J＝4.3,2.6 Hz,1H),5.91(dd,J＝5.6,2.6 Hz,1H),5.82(dd,J＝4.5,3.0Hz,1H),1.25(s,18H)；13C NMR(101 MHz,DMSO)δ177.91,152.88,141.27,138.55,133.76,132.19,129.34,127.86,125.39,123.62,121.61,118.97,109.59,107.37,106.27,57.37,34.43,30.15；IR(film):γ＝3637,3201,2956,2925,1706,1645,1540,1471,1436,1247,955,803,750,608 cm-1；HRMS(EI-TOF):calcd for C26H30 N2O2 402.2707,found 402.2701.

Claims (5)

1.一种3,3-二取代-2-吲哚酮衍生物,其特征在于，它是具有如下结构式的消旋体、左旋或右旋的光学活性体；
式中：R1和R6选自H、三氟甲基、二氟甲基、苄基、烯丙基、C1～C4烷基，R2～R5和R7～R11选自H、卤素、硝基、三氟甲基、二氟甲基、环丙基、环丁基、环戊基、环己基、苄氧基、苯氧基、苄基、C1～C4烷基或C1～C4烷氧基。
2.制备权利要求1所述的3,3-二取代-2-吲哚酮衍生物的方法，其特征在于，以靛红衍生的醌甲基化物类化合物为原料，跟亲核试剂反应，以螺环磷酸为催化剂，在有机溶剂中于10～80℃，反应12～48小时，纯化得到3,3-二取代-2-吲哚酮衍生物，所述的靛红衍生的醌甲基化物类化合物和亲核试剂的摩尔比为1：1～1.2，螺环磷酸催化剂和靛红衍生的醌甲基化物类化合物的摩尔比为5～20：100。
3.根据权利要求2所述的3,3-二取代-2-吲哚酮衍生物的制备方法，其特征在于，所述的螺环磷酸催化剂为具有结构式(1)的化合物，可以是消旋体、左旋或右旋的光学活性体：
式中：R选自H、烷基、芳基或取代的芳基、9-蒽基、菲基，取代的芳基上的取代基是一个或多个，包括卤素、硝基、三氟甲基、二氟甲基、环丙基、环丁基、环戊基、环己基、苄氧基、苯氧基、苄基、苯基、C1～C4烷基或C1～C4烷氧基。
4.根据权利要求2所述的3,3-二取代-2-吲哚酮衍生物的制备方法，其特征在于，所述的靛红衍生的醌甲基化物类化合物结构如下式(2)所示：
所述的亲核试剂为吡咯类化合物或吲哚类化合物，结构如下式(3)和式(4)所示：
式中：R1～R11如权利要求1所述。
5.根据权利要求2所述的3,3-二取代-2-吲哚酮衍生物的制备方法，其特征在于，所述的有机溶剂为甲苯、二甲苯、苯、二氯甲烷、氯仿、1,2-二氯乙烷、氟苯、四氢呋喃、氯苯或乙基苯。
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112010796A (zh) * 2020-09-17 2020-12-01 浙江大学 光学活性3-(1,1-二氟-2-氧-2-芳基乙基)异吲哚啉-1-酮衍生物制备方法
CN113773243A (zh) * 2021-09-01 2021-12-10 大连理工大学 一种有机催化氧化吲哚自缩合制备异靛蓝类化合物的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008129075A1 (en) * 2007-04-24 2008-10-30 Topotarget A/S Substituted 3-(4-hydroxyphenyl)-indolin-2-one-compounds
CN103073583A (zh) * 2013-02-20 2013-05-01 浙江大学 手性螺环磷酸催化制备光学活性α-氨基膦酸酯衍生物的方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008129075A1 (en) * 2007-04-24 2008-10-30 Topotarget A/S Substituted 3-(4-hydroxyphenyl)-indolin-2-one-compounds
CN103073583A (zh) * 2013-02-20 2013-05-01 浙江大学 手性螺环磷酸催化制备光学活性α-氨基膦酸酯衍生物的方法

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ABDUL RAHMAN ET AL.: "Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindoles via a 1,6-conjugate addition reaction", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 *
ABDUL RAHMAN: "手性螺环磷酸不对称催化合成光学活性含氮杂环化合物的研究", 《中国博士学位论文全文数据库 工程科技I辑》 *
LAKSHMANA K. ET AL.: "：Friedel–Crafts alkylations of electron-rich aromatics with 3-hydroxy-2-oxindoles: scope and limitations", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 *
LAN TAN ET AL.: "An Economical, Sustainable Pathway to Indole-Containing Oxindoles: Iron-Catalyzed 1,6-Conjugate Addition in Glycerol", 《SUSTAINABILITY》 *
ZENGWEI LAI ET AL.: "Organocatalytic Asymmetric Nucleophilic Addition to o‑Quinone Methides by Alcohols", 《ORGANIC LETTERS》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112010796A (zh) * 2020-09-17 2020-12-01 浙江大学 光学活性3-(1,1-二氟-2-氧-2-芳基乙基)异吲哚啉-1-酮衍生物制备方法
CN113773243A (zh) * 2021-09-01 2021-12-10 大连理工大学 一种有机催化氧化吲哚自缩合制备异靛蓝类化合物的方法
CN113773243B (zh) * 2021-09-01 2023-01-06 大连理工大学 一种有机催化氧化吲哚自缩合制备异靛蓝类化合物的方法

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