CN110845386A - 一种铁催化合成吡咯的方法、吡咯及应用 - Google Patents
一种铁催化合成吡咯的方法、吡咯及应用 Download PDFInfo
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims abstract description 97
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 29
- 229910052742 iron Inorganic materials 0.000 title claims abstract description 19
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 18
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000012074 organic phase Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000000047 product Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 8
- 238000000746 purification Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims abstract description 8
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 238000001953 recrystallisation Methods 0.000 claims abstract description 7
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 7
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims abstract description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims abstract description 5
- 238000012544 monitoring process Methods 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- -1 pyrrole compound Chemical class 0.000 claims abstract description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims abstract description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 5
- PGJLOGNVZGRMGX-UHFFFAOYSA-L iron(2+);trifluoromethanesulfonate Chemical compound [Fe+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PGJLOGNVZGRMGX-UHFFFAOYSA-L 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 238000013040 rubber vulcanization Methods 0.000 claims description 2
- 150000003851 azoles Chemical class 0.000 claims 2
- 230000008034 disappearance Effects 0.000 claims 1
- 239000004848 polyfunctional curative Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 8
- 230000035484 reaction time Effects 0.000 abstract description 6
- 230000036632 reaction speed Effects 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- OSHOQERNFGVVRH-UHFFFAOYSA-K iron(3+);trifluoromethanesulfonate Chemical compound [Fe+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F OSHOQERNFGVVRH-UHFFFAOYSA-K 0.000 description 1
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
本发明属于有机合成化学技术领域,公开了一种铁催化合成吡咯的方法、吡咯及应用,在干燥的圆底烧瓶中加入化合物1a,4‑氯苯胺2a和三氟甲磺酸铁,甲苯1mL;保持110℃搅拌10h,TLC监测至底物1消失,反应结束;将反应液倒入饱和氯化钠溶液中,用乙醚萃取,合并有机相;利用无水MgSO4干燥,浓缩有机相;经过硅胶柱层析,利用乙醚作为溶剂对粗产品进行重结晶纯化,得到纯产物。本发明采用新型铁系催化剂、高效合成吡咯化合物,反应时间短,仅为10小时;使用的催化剂用量更少,反应速度更快;同时本发明的制备工艺简单,所用试剂量少,也不会产生有毒产物。
Description
技术领域
本发明属于有机合成化学技术领域,尤其涉及一种铁催化合成吡咯的方法、吡咯及应用。
背景技术
目前,业内常用的现有技术是这样的:现有制备吡咯的方法往往是从α-羰基环丙烷结构出发,先生成二氢吡咯,之后在氧化剂的作用下才能够制备吡咯。分步法合成操作繁琐,浪费试剂和时间,造成了极大的污染,分步法合成需要每一步的合成都进行添加试剂-等待反应结束-停止反应-纯化等步骤,不论是从时间上、操作上还是从试剂的用量上都会造成浪费,同时由于大量使用有机试剂,会在一定程度上造成污染。同时现有采用三氯化铁催化剂一步制备吡咯的反应反应时间长达21小时。
现有合成分子式如下:
综上所述,现有技术存在的问题是:
(1)现有分步合成方法合成操作繁琐,浪费试剂和时间,污染严重。
(2)现有采用三氯化铁催化剂一步制备吡咯的技术反应时间长。
解决上述技术问题的难度:
(1)改变分步合成方法需要找到合适反应条件,为了避免污染,还要注意选择绿色催化剂。
(2)目前一步反应制备吡咯的反应时间过长,说明选用的三氯化铁催化剂的催化活性不高,选择催化活性更高的催化剂,同时避免环境污染,是提高该反应效率的关键问题。
解决上述技术问题的意义:改变了分步法合成的种种弊端,在三氟化铁催化下一步实现了多官能化吡咯的合成,反应时间大大缩短,反应效率大幅度提高。
发明内容
针对现有技术存在的问题,本发明提供了一种铁催化合成吡咯的方法、吡咯及应用。
本发明是这样实现的,一种铁催化合成吡咯的方法,所述铁催化合成吡咯的方法具体包括:
以三氟甲磺酸铁作为催化剂,甲苯作为溶剂,从α-羰基环丙烷和胺出发,制备含有多官能化吡咯化合物。本发明合成的吡咯能够含有多种官能团,具有能够进一步反应合成其他化合物的可能性,同时在许多药物中含有吡咯骨架,因此合成的吡咯化合物具有潜在的药用价值等。
进一步,所述铁催化合成吡咯的方法反应方程式如下:
进一步,所述铁催化合成吡咯的方法具体包括以下步骤:
步骤一,在干燥的圆底烧瓶中加入化合物1a,4-氯苯胺2a和三氟甲磺酸铁,甲苯(1mL);
步骤二,保持110℃搅拌10h,TLC监测至底物1消失,反应结束;
步骤三,将反应液倒入饱和氯化钠溶液中,用乙醚萃取,合并有机相;
步骤四,利用无水MgSO4干燥,浓缩有机相;
步骤五,经过硅胶柱层析,利用乙醚作为溶剂对粗产品进行重结晶纯化,得到纯产物。
进一步,所述铁催化合成吡咯的方法包括以下步骤:
(1)在干燥的圆底烧瓶中加入化合物1a 604mg,1.0mmol,4-氯苯胺2a 70.3mg,0.5mmol和三氟甲磺酸铁27.5mg,0.30mmol,甲苯1mL;搅拌,TLC 监测至底物1a消失,反应结束;
(2)将反应液倒入30mL饱和氯化钠溶液中,用3×15mL乙醚萃取,合并有机相;经过无水MgSO4干燥,浓缩有机相;
(3)最后经过硅胶柱层析,并利用乙醚作为溶剂对粗产品进行重结晶纯化,得到纯产物3aa为白色固体。
本发明的另一目的在于提供一种由所述铁催化合成吡咯的方法合成的吡咯。
本发明的另一目的在于提供一种所述吡咯在有机合成中的应用。
本发明的另一目的在于提供一种所述吡咯在医药制造中的应用。
本发明的另一目的在于提供一种所述吡咯在橡胶硫化促进剂、环氧树脂固化剂制备中的应用。
综上所述,本发明的优点及积极效果为:本发明采用新型铁系催化剂、高效合成吡咯化合物,反应时间短,仅为10小时;使用的催化剂用量更少,反应速度更快;同时本发明的制备工艺简单,所用试剂量少,也不会产生有毒产物。
附图说明
图1是本发明实施例提供的铁催化合成吡咯的方法流程图。
图2是本发明实施例提供的铁催化合成吡咯的方法1H NMR,13C NMR分析结果图;
图中:(a)1H NMR核磁谱图;(b)13C NMR核磁谱图。
图3是本发明实施例提供的铁催化合成吡咯的方法1H NMR,13C NMR分析图;
图中:(a)1H NMR核磁谱图;(b)13C NMR核磁谱图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
针对现有技术存在的问题,本发明提供了一种铁催化合成吡咯的方法、吡咯及应用,下面结合附图对本发明作详细的描述。
本发明实施例提供的铁催化合成吡咯的方法包括:以三氟甲磺酸铁作为催化剂,甲苯作为溶剂,从α-羰基环丙烷和胺出发,制备含有多官能化吡咯化合物。
本发明实施例提供的铁催化合成吡咯的方法反应方程式如下:
如图1所示,本发明实施例提供的铁催化合成吡咯的方法具体包括以下步骤:
S101,在干燥的圆底烧瓶中加入化合物1a,4-氯苯胺2a和三氟甲磺酸铁,甲苯(1mL)。
S102,保持110℃搅拌10h,TLC监测至底物1消失,反应结束。
S103,将反应液倒入饱和氯化钠溶液中,用乙醚萃取,合并有机相。
S104,利用无水MgSO4干燥,浓缩有机相。
S105,经过硅胶柱层析,利用乙醚作为溶剂对粗产品进行重结晶纯化,得到纯产物。
下面结合具体实施例对本发明的技术方案与技术效果做进一步说明。
实施例1:吡咯化合物3aa的制备
在干燥的圆底烧瓶中加入化合物1a(604mg,1.0mmol),4-氯苯胺2a(70.3 mg,0.5mmol)和三氟甲磺酸铁(27.5mg,0.30mmol),甲苯(1mL)。保持110 ℃搅拌10h,TLC监测至底物1消失,反应结束。将反应液倒入饱和氯化钠溶液(30mL)中,用乙醚(3×15mL)萃取,合并有机相。经过无水MgSO4干燥,浓缩有机相。最后经过硅胶柱层析,并利用乙醚作为溶剂对粗产品进行重结晶纯化,得到纯产物3aa为白色固体,收率为60%。
N,1-Bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxamide(3aa).Theproduct was isolated by flash chromatography(eluent:petroleum ether/ethylacetate= 10/2)as a white solid(235mg,68%).Mp 184-186℃;1H NMR(400MHz,CDCl3)δ7.56(d,J=8.4Hz,3H),7.46(d,J=8.4Hz,2H),7.29(d,J=8.4Hz,2H),7.23(d,J =8.4Hz,2H),6.70(s,1H),6.48(s,1H),2.48(s,3H).13C NMR(100MHz,CDCl3) δ163.9,137.6,137.2,135.3,134.2,129.7,129.1,128.8,127.6,121.5,121.3,116.2, 107.1,12.2.HRMS(ESI),m/zcalcd for C18H14Cl2N2O([M+Na]+)367.0375;found, 367.0399.
1-(4-Chlorophenyl)-2-methyl-N-(p-tolyl)-1H-pyrrole-3-carboxamide(3ab).The product was isolated byflashchromatography(eluent:petroleum ether/ethyl acetate= 10/2)as a white solid(221mg,60%).Mp 180-182℃;1H NMR(400MHz,CDCl3) δ7.49(d,J=8.4Hz,3H),7.47-7.44(m,2H),7.23(d,J=8.4Hz,2H),7.15(d,J=8.4Hz,2H),6.70(d,J=3.2Hz,1H),6.48(d,J=3.2Hz,1H),2.48(s,3H),2.33(s, 3H).13CNMR(100MHz,CDCl3)δ163.9,137.7,136.0,134.8,134.1,133.5,129.7,129.6,127.6,121.3,120.2,116.7,107.1,22.0,12.2.HRMS(ESI),m/z calcd for C19H17ClN2O([M+H]+)325.1102;found,325.1131。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等,均应包含在本发明的保护范围之内。
Claims (10)
1.一种铁催化合成吡咯的方法,其特征在于,所述铁催化合成吡咯的方法以三氟甲磺酸铁作为催化剂,甲苯作为溶剂,从d-羰基环丙烷和胺出发,制备含有多官能化吡咯化合物。
3.如权利要求1所述的铁催化合成吡咯的方法,其特征在于,所述铁催化合成吡咯的方法具体包括以下步骤:
步骤一,在干燥的圆底烧瓶中加入化合物1a,4-氯苯胺2a和三氟甲磺酸铁,甲苯1mL;
步骤二,保持110℃搅拌10h,TLC监测至底物1消失,反应结束;
步骤三,将反应液倒入饱和氯化钠溶液中,用乙醚萃取,合并有机相;
步骤四,利用无水MgSO4干燥,浓缩有机相;
步骤五,经过硅胶柱层析,利用乙醚作为溶剂对粗产品进行重结晶纯化,得到纯产物。
4.如权利要求1所述的铁催化合成吡咯的方法,其特征在于,所述铁催化合成吡咯的方法包括以下步骤:
(1)在干燥的圆底烧瓶中加入化合物1a 604mg,1.0mmol,4-氯苯胺2a 70.3mg,0.5mmol和三氟甲磺酸铁27.5mg,0.30mmol,甲苯1mL;搅拌,TLC监测至底物1消失,反应结束;
(2)将反应液倒入饱和氯化钠溶液中,用乙醚萃取,合并有机相;经过无水MgSO4干燥,浓缩有机相;
(3)最后经过硅胶柱层析,并利用乙醚作为溶剂对粗产品进行重结晶纯化,得到纯产物3aa为白色固体。
5.如权利要求4所述的铁催化合成吡咯的方法,其特征在于,保持110℃搅拌10h,TLC监测至底物1消失,反应结束。
6.如权利要求4所述的铁催化合成吡咯的方法,其特征在于,将反应液倒入饱和氯化钠溶液30mL中,用乙醚3×15mL萃取,合并有机相。
7.一种由权利要求1~6任意一项所述铁催化合成吡咯的方法合成的吡咯。
8.一种如权利要求7所述吡咯在有机合成中的应用。
9.一种如权利要求7所述吡咯在医药制造中的应用。
10.一种如权利要求7所述吡咯在橡胶硫化促进剂、环氧树脂固化剂制备中的应用。
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CN1931839A (zh) * | 2006-09-27 | 2007-03-21 | 温州大学 | 一种n-取代吡咯的合成方法 |
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