CN102875448A - 一种制备吲哚螺环戊烷衍生物的合成方法 - Google Patents
一种制备吲哚螺环戊烷衍生物的合成方法 Download PDFInfo
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Abstract
本发明属于有机化学技术领域,具体为一种吲哚螺环戊烷衍生物合成方法。本发明使用3-丁炔-2-酮衍生物和3位具有炔亚甲基取代的吲哚酮衍生物为原料,在三苯基磷催化下通过[3+2]环加成反应合成一种丰富官能团的吲哚螺环戊烷衍生物,此类化合物骨架具有广谱的生物活性,在药物研发中具有潜在的应用前景。
Description
技术领域
本发明涉及有机化学技术领域,具体为一种吲哚螺环戊烷衍生物的合成方法。
背景技术
吲哚螺环化合物是一类重要杂环化合物,广泛存在于天然产物和药物活性成分当中,具有多种药理活性。例如,其对NNRTIs型HIV-1具有抑制活性(Jiang T.Bioorg.Med.Chem.Lett.2006,16,2105)、对甘氨酸受体具有拮抗作用(Hershenson,F.M.;Prodan,K.A.,et al.J.Med.Chem.1977,20,1448)、以及对肿瘤具有抑制活性(Numata,A.,Takada,T,et al.J.Tetrahedron lett.1993,34,2355)。因此,吲哚螺环化合物的合成受到人们的广泛关注。随着吲哚合成化学的发展,氮杂、氧杂等杂环吲哚螺环衍生物的一步合成方法相继被发现,但吲哚螺环戊烷衍生物的简便合成方法鲜见报道。因此,开发以简单结构的起始原料,一步合成吲哚螺环戊烷衍生物的方法具有重要的实际应用价值。本发明提供了一种简单、方便、新颖的制备丰富官能团的吲哚螺环戊烷衍生物的新技术。
发明内容
本发明使用吲哚酮衍生物1与3-丁炔-2-酮衍生物2在三苯基磷催化下发生[3+2]环化反应,制得吲哚螺环戊烷类衍生物3,其反应式如下:
其中化合物1为吲哚酮衍生物,R1为H或CH3、OCH3等各种供电子基团或F、Cl、CF3等各种吸电子基团,R2为Ph或4-Me-C6H4、4-MeOC6H4、3,4-MeOC6H3、4-Cl-C6H4、3-Cl-C6H4、2-Cl-C6H4、4-F-C6H4等含各种取代基的苯基及2-naphthyl,2-furanyl等基团,化合物2为3-丁炔-2-酮衍生物,R3为Ph或4-Me-C6H4,4-MeOC6H4,3,4-MeOC6H3等各种含供电子基团的芳基或4-F-C6H4,4-CF3-C6H4,4-Cl-C6H4等各种含吸电子基团的芳基。
具体操作步骤为:
吲哚酮类衍生物1,3-丁炔-2-酮衍生物2溶于有机溶剂中,加入有机磷试剂,于室温反应至反应基本完全,浓缩后用柱层析分离得到相应的吲哚螺环戊烷类化合物。
该反应起始原料易得,条件温和,合成路线简短、操作方便,成本较低,而且通过此法合成的吲哚螺环戊烷衍生物具有潜在的生物活性,在新药研发领域有较好的应用前景。
本发明的较佳反应条件为:
(1)催化剂为PPh3;
(2)吲哚酮类衍生物、PPh3与3-丁炔-2-酮衍生物的摩尔比例为1∶0.5∶2;
(2)溶剂为二氯甲烷∶乙酸乙酯=9∶1;
(3)反应温度为室温。
具体实施方式
下面的实施例是对本发明的进一步说明,而不是限制本发明的范围。
实施例1化合物3a的合成
(E)-1-苄基-3-(3-苯基-2-丙炔基)二氢吲哚-2-酮(0.1mmol),4-苯基-3-丁炔-2-酮(0.2mmol)溶于1mL二氯甲烷/乙酸乙酯(9/1)中,加入催化剂PPh3(0.05mmol),室温反应48h,浓缩后用柱层析分离得到相应的吲哚螺环戊烷衍生物3a,收率63%。IR(KBr):v=3059,3028,1718,1690,1619,1588,1447,1362,1184,1168,908,870,762,696cm-1.1H NMR(500MHz,CDCl3)δ7.82(s,1H),7.35-7.27(m,3H),7.24-7.21(m,3H),7.16-7.05(m,7H),6.97(t,J=8.0Hz,2H),6.89-6.86(m,2H),6.82(d,J=7.5Hz,2H),6.78(d,J=8.0Hz,1H),5.08(d,J=16.0Hz,1H),4.36(d,J=16.0Hz,1H),3.85(dd,J=11.5,7.5Hz,1H),3.16(dd,J=13.0,8.0Hz,1H),2.98(dd,J=13.0,6.5Hz,1H).13C NMR(125MHz,CDCl3)δ202.44,175.67,142.82,138.63,136.17,135.24,134.25,131.74,130.99,129.74,129.37,129.04,128.80,128.30,128.20,128.13,127.54,127.24,124.35,123.03,122.53,109.67,86.13,85.69,59.46,44.38,42.52,38.65.HRMS(ESI):calcd.for C34H26NO2[M+H]+480.1958;found480.1951.
实施例2化合物3b的合成
(E)-1-苄基-5-氯-3-(3-苯基-2-丙炔基)二氢吲哚-2-酮(0.1mmol),4-苯基-3-丁炔-2-酮(0.2mmol)溶于1mL二氯甲烷/乙酸乙酯(9/1)中,加入催化剂PPh3(0.05mmol),室温反应48h,浓缩后柱层析分离得到相应的吲哚螺环戊烷衍生物3b,收率72%。1H NMR(300MHz,CDCl3)δ7.84(s,1H),7.24(d,J=2.1Hz,2H),7.23-7.19(m,2H),7,19-7.17(m,2H),7.17-7.01(m,6H),7.00-6.94(m,2H),6.80(d,J=7.2Hz,2H),6.68(d,J=8.3Hz,1H),5.04(d,J=15.8Hz,1H),4.37(d,J=15.8Hz,1H),3.83(dd,J=10.8,8.0Hz,1H),3.21(dd,J=18.0,8.0Hz,1H),2.96(dd,J=18.0,10.8Hz,1H).13C NMR(75MHz,CDCl3)δ201.97,174.42,166.50,154.59,148.63,141.49,141.37,139.20,135.41,135.22,134.79,134.05,133.99,133.08,132.16,131.74,130.04,129.89,129.25,129.16,129.02,128.93,128.90,128.70,128.60,128.52,128.40,128.31,128.17,127.97,127.79,127.55,127.28,125.01,123.37,122.23,120.79,110.57,110.48,105.16,97.35,85.75,59.33,44.49,42.36,38.52.HRMS(ESI):calcd.for C34H25ClNO2[M+H]+514.1568;found514.1567.
实施例3化合物3c的合成
(E)-1-苄基-5-氯-3-(3-苯基-2-丙炔基)二氢吲哚-2-酮(0.1mmol),4-苯基-3-丁炔-2-酮(0.2mmol)溶于1mL二氯甲烷/乙酸乙酯(9/1)中,加入催化剂PPh3(0.05mmol),室温反应48h,浓缩后柱层析分离得到相应的吲哚螺环戊烷衍生物3c,收率58%。IR(KBr):v=3057,3030,2920,2852,1731,1718,1617,1558,1541,1508,1490,1455,1450,1186,1175,861,758,694cm-1.1H NMR(300MHz,CDCl3)δ7.84(s,1H),7.28-7.17(m,6H),7.14-7.02(m,5H),6.99-6.92(m,4H),6.81(d,J=7.2Hz,2H),6.68(dd,J=9.3,4.2Hz,1H),5.06(d,J=15.9Hz,1H),4.37(d,J=15.9Hz,1H),3.85(dd,J=11.1,8.1Hz,1H),3.21(dd,J=18.0,8.1Hz,1H),2.95(dd,J=18.0,11.1Hz,1H).13C NMR(75MHz,CDCl3)δ201.98,175.56,160.92,139.18,138.88,135.52,134.98,134.03,131.72,129.86,129.37,129.23,128.92,128.69,128.49,128.30,128.16,127.75,127.32,122.32,115.43,114.77,112.92,110.15,86.00,85.82,44.57,42.41,38.51,29.84.HRMS(ESI):calcd.for C34H25FNO2[M+H]+498.1864;found498.1862.
实施例4化合物3d的合成
(E)-1-苄基-3-{3-(4-氟代苯基)-2-丙炔基}二氢吲哚-2-酮(0.1mmol),4-苯基-3-丁炔-2-酮(0.2mmol)溶于1mL二氯甲烷/乙酸乙酯(9/1)中,加入催化剂PPh3(0.05mmol),室温反应48h,浓缩后柱层析分离得到相应的吲哚螺环戊烷衍生物3e,收率50%。IR(KBr):v=3066,3032,2922,2854,1718,1698,1654,1616,1609,1558,1506,1488,1458,1362,1179,1155,831,754,699cm-1.1H NMR(300MHz,CDCl3)δ7.81(s,1H),7.42-7.27(m,5H),7.22-7.15(m,2H),7.12-7.06(m,3H),7.03-6.96(m,2H),6.86-6.77(m,6H),5.08(d,J=15.9Hz,1H),4.33(d,J=15.6Hz,1H),3.83(dd,J=15.0,6.8Hz,1H),3.15(dd,J=18.0,8.0Hz,1H),2.97(dd,J=18.3,11.7Hz,1H).13C NMR(75MHz,CDCl3)δ202.30,175.60,164.18,141.18,138.70,136.09,135.28,134.23,133.65,133.63,131.44,129.78,129.36,129.04,128.79,128.14,127.61,127.30,124.30,123.03,115.61,109.62,85.85,84.61,44.38,42.44,38.61,35.88.HRMS(ESI):calcd.for C34H25F NO2[M+H]+498.1864;found498.1871.
实施例5化合物3e的合成
(E)-1-苄基-3-{3-(2-氯代苯基)-2-丙炔基}二氢吲哚-2-酮(0.1mmol),4-苯基-3-丁炔-2-酮(0.2mmol)溶于1mL二氯甲烷/乙酸乙酯(9/1)中,加入催化剂PPh3(0.05mmol),室温反应48h,浓缩后柱层析分离得到相应的吲哚螺环戊烷衍生物3f,收率61%。IR(KBr):v=3064,3031,2919,2849,1716,1698,1654,1616,1558,1515,1179,753,696cm-1.1H NMR(300MHz,CDCl3)δ7.81(s,1H),7.31-7.14(m,7H),7.10-6.97(m,7H),6.84(dd,J=8.0,1.5Hz,1H),6.78-6.76(m,3H),5.06(d,J=16.0Hz,1H),4.36(d,J=16.0Hz,1H),3.91(dd,J=12.0,8.0Hz,1H),3.20(dd,J=18.0,8.0Hz,1H),3.04(dd,J=18.0,11.5Hz,1H).13C NMR(300MHz,CDCl3)δ202.23,175.57,142.80,138.62,136.24,135.90,135.24,134.18,133.71,131.38,130.79,129.73,129.34,129.12,128.94,128.71,128.12,127.56,127.34,126.29,124.45,123.15,122.49,109.84,91.38,82.39,59.28,44.36,42.49,38.67.HRMS(ESI):calcd.for C34H25ClNO2[M+H]+514.1568;found514.1578.
实施例6化合物3f的合成
(E)-1-苄基-3-(3-苯基-2-丙炔基)二氢吲哚-2-酮(0.1mmol),4-(4-氟-苯基)-3-丁炔-2-酮(0.2mmol)溶于1mL二氯甲烷/乙酸乙酯(9/1)中,加入催化剂PPh3(0.05mmol),室温反应48h,浓缩后柱层析分离得到相应的吲哚螺环戊烷衍生物3h,收率43%。IR(KBr):v=3061,3031,2934,2903,1725,1701,1696,1628,1612,1599,1506,1468,1225,1180,1113,1094,894,843,769,752,695cm-1.1H NMR(300MHz,CDCl3)δ7.75(s,1H),7.63-7.50(m,1H),7.47-7.26(m,4H),7.25-6.98(m,8H),6.90-6.71(m,5H),5.07(d,J=15.6Hz,1H),4.47(d,J=15.6Hz,1H),3.87-3.80(dd,J=12.3,7.8Hz,1H),3.17(dd,J=18.0,8.1Hz,1H),2.98(dd,J=18.0,11.4Hz,1H).13C NMR(75MHz,CDCl3)δ202.27,175.60,165.02,142.70,142.32,137.33,136.99,135.59,135.47,131.69,131.55,131.10,129.15,128.82,128.32,128.19,127.68,127.40,124.44,123.09,115.47,109.66,109.13,86.00,85.75,44.40,43.35,42.46,38.71.HRMS(ESI):calcd.for C34H25F NO2[M+H]+498.1864;found498.1872.
Claims (5)
1.一种吲哚螺环戊烷衍生物的合成方法,包含以下步骤:其特征在于3位具有炔亚甲基取代的吲哚酮衍生物在温和条件下与3-丁炔-2-酮衍生物反应,在有机磷试剂催化下发生环合反应,制得一种吲哚螺环戊烷类化合物,其反应式如下:
具体操作步骤为:
吲哚酮类衍生物1,3-丁炔-2-酮衍生物2溶于有机溶剂中,加入有机磷试剂,于室温反应至反应基本完全,浓缩后柱层析分离得到相应的吲哚螺环戊烷类化合物。
R1为H或CH3,OCH3等各种供电子基团或F,Cl,CF3等各种吸电子基团;
R2为Ph或4-Me-C6H4,4-MeOC6H4,3,4-MeOC6H4,4-Cl-C6H4,3-Cl-C6H4,2-Cl-C6H4,4-F-C6H4,4-CF3-C6H4等含有不同取代基的苯环及2-naphthyl,2-furanyl等;
R3为Ph或4-Me-C6H4,4-MeOC6H4,3,4-MeOC6H4各种供电子基团的苯环或4-F-C6H4,4-CF3-C6H4,4-Cl-C6H4等各种吸电子基团的苯环。
2.如权利要求1所述的方法,其特征在于催化剂为有机磷试剂,优选三苯基磷(PPh3)。
3.如权利要求1所述的方法,其特征在于吲哚酮类衍生物、有机磷试剂与3-丁炔-2-酮衍生物的摩尔比例为1∶0.02~0.5∶0.2~3,优选吲哚酮类衍生物、有机磷试剂与3-丁炔-2-酮衍生物的摩尔比例为1∶0.5∶2的实验方案。
4.如权利要求1所述的方法,溶剂为甲苯、二氯甲烷、二氯乙烷、氯仿等,优选二氯甲烷∶乙酸乙酯=9∶1为溶剂。
5.如权利要求1所述的方法,反应温度为0~100℃,优选室温。
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CN107778320A (zh) * | 2017-10-23 | 2018-03-09 | 青岛大学 | 一种螺环异恶唑啉类化合物的合成方法 |
CN111704571A (zh) * | 2020-07-20 | 2020-09-25 | 南宁师范大学 | 光学活性2-芳基螺环[环戊烷-1,3’-吲哚]-3-甲醛的制备方法 |
CN114805182A (zh) * | 2022-04-29 | 2022-07-29 | 常州大学 | 一种可见光催化合成吲哚螺环丙烷类化合物的方法 |
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