CN106278993B - 一种金催化的多取代吡咯的合成方法 - Google Patents
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 9
- 238000006555 catalytic reaction Methods 0.000 title claims description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 title claims description 6
- 229910052737 gold Inorganic materials 0.000 title claims description 6
- 239000010931 gold Substances 0.000 title claims description 6
- 150000003233 pyrroles Chemical class 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- -1 alkynes compound Chemical class 0.000 claims abstract description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003851 azoles Chemical class 0.000 claims abstract description 8
- WCGIGOVLOFXAMG-UHFFFAOYSA-N silver;trifluoromethanesulfonic acid Chemical compound [Ag].OS(=O)(=O)C(F)(F)F WCGIGOVLOFXAMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 206010011224 Cough Diseases 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005695 Ammonium acetate Substances 0.000 abstract description 3
- 229940043376 ammonium acetate Drugs 0.000 abstract description 3
- 235000019257 ammonium acetate Nutrition 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- OJRHUICOVVSGSY-RXMQYKEDSA-N (2s)-2-chloro-3-methylbutan-1-ol Chemical compound CC(C)[C@H](Cl)CO OJRHUICOVVSGSY-RXMQYKEDSA-N 0.000 description 1
- RYKLZUPYJFFNRR-UHFFFAOYSA-N 3-hydroxypiperidin-2-one Chemical compound OC1CCCNC1=O RYKLZUPYJFFNRR-UHFFFAOYSA-N 0.000 description 1
- 238000006086 Paal-Knorr synthesis reaction Methods 0.000 description 1
- 229930003779 Vitamin B12 Natural products 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 229960001770 atorvastatin calcium Drugs 0.000 description 1
- FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明涉及一种1,2,5‑三取代1,4,5,6‑四氢‑环戊烷并[b]吡咯类化合物的合成方法，其反应通式如下所示
Description
技术领域
本发明属于有机合成技术领域，具体涉及一种1,2,5-三取代1,4,5,6-四氢环戊烷并[b]吡咯类化合物的合成方法。
背景技术
吡咯杂环是一类重要的骨架结构，在有机合成化学，药物化学，材料化学中有广泛的应用，比如维生素B12、阿托伐他汀钙、多聚吡咯复合材料等。1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯是重要的吡咯杂环化合物，目前针对该类化合物的合成策略是先制备1、4-二酮羰基中间体，再将该中间体与醋酸铵经过帕尔－克诺尔吡咯合成(Paal-Knorr吡咯合成)反应得到，步骤繁琐(Thompson,B.B.；Montgomery,J.Organic Letters 2011,13,3289)。本发明创造性地运用邻二羟基炔烃与有机伯胺或醋酸铵在三苯基磷氯化金和三氟甲烷磺酸银的催化作用下一锅法合成1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物。克服了已有制备方法的缺点，原料易得，反应条件温和。因此本发明有良好的实用价值和社会经济效率，对同类产品及下游产品的工艺开发具有很好的借鉴意义。
发明内容
本发明的目的在于克服现有制备技术步骤繁琐的不足,为1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物的合成提供一种简洁高效的合成路线。
本发明的技术方案为：一种1,2,5-三取代1,4,5,6-四氢环戊烷并[b]吡咯类化合物的合成方法。其技术特征为：邻二羟基炔烃类化合物、三苯基磷氯化金和三氟甲烷磺酸银依次加入有机溶剂中，加热条件反应1小时候后再加入胺继续反应，得到1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物，反应式如下:
其中R1可为叔丁基，苯基、4-甲氧基苯基，4-甲基苯基；R2可为苯基、氢；R3为氢，乙基，丙基，丁基，异丁基，环丙基，环己基，苯基，苄基，邻氯苯基，对氯苯基，对溴苯基，对硝基苯基，对甲氧基苄基，3-甲氧基丙基，炔丙基。
在上述方法反应中用的溶剂选自：正庚烷、正己烷、环己烷、正壬烷、甲苯、四氢呋喃的一种或几种。优选正庚烷。
在上述方法反应中加热的温度为60-120℃，维持时间为4-10小时。
在上述方法反应中，反应中各物质的物质的量比为：邻二羟基炔类化合物：三苯基磷氯化金：三氟甲烷磺酸银：胺：溶剂＝1:0.05-0.20:0.05-0.20:2-5:10-100。
具体实施方式
以下通过具体实施例对本发明做进一步的说明，但不应该将此理解为本发明上述主题的范围仅限于以下的实施例，凡基于本发明上述内容实现的技术均属于本发明的范围。
实施例
以醋酸胺为原料(反应式1)
将邻二羟基炔烃类化合物a(50mg,0.25mmol),加入到搅拌的正庚烷中(1mL),随后依次加入三苯基磷氯化金(6.2mg,0.0125mol)和三氟甲烷磺酸银(3.2mg,0.0125mol)在80℃下反应1小时后再加入醋酸胺(88mg,1.25mmol)，继续在80℃体系中反应5小时。在旋转蒸发仪上抽干溶剂，经柱层析得到浅褐色的油状液体(33.4mg，74％)。
产物检测数据如下：
1H NMR(400MHz,CDCl3)δ8.10(s,1H),7.44-7.42(m,2H),7.36-7.32(m,2H),7.18-7.15(m,1H),6.32(d,J＝1.8Hz,1H),2.77(t,J＝7.1Hz,2H),2.67(t,J＝6.9Hz,2H),2.49–2.41(m,2H)；13C NMR(100MHz,CDCl3):δ＝13C NMR(100MHz,CDCl3):δ＝137.92,135.17,133.65,128.77,128.54,125.48,123.25,101.64,30.90,29.03,25.42.
以正丁胺为原料(反应式2)
将邻二羟基炔烃类化合物a(50mg,0.25mmol),加入到搅拌的正庚烷中(1mL),随后依次加入三苯基磷氯化金(6.2mg,0.0125mmol)和三氟甲烷磺酸银(3.2mg,0.0125mmol)在80℃下反应1小时后再加入正丁胺(73ul,0.75mmol)，继续在80℃体系中反应5小时。在旋转蒸发仪上抽干溶剂，经柱层析得到浅褐色的油状液体(33.1mg，56％)。
产物检测数据如下：
1H NMR(400MHz,CDCl3):δ＝7.43–7.30(m,4H),7.28-7.24(m,1H),5.98(s,1H),3.83(t,J＝8.0Hz,2H),2.75(t,J＝7.0Hz,2H),2.67(t,J＝7.0Hz,2H),2.48–2.38(m,2H),1.61-1.57(m,2H),1.23-1.20(m,2H),0.82(t,J＝7.4Hz,3H)；13C NMR(101MHz,CDCl3):δ＝139.82,137.22,134.38,128.62,128.29,126.31,125.60,103.52,45.54,33.27,28.75,25.48,25.26,19.85,13.63.
以苯胺为原料(反应式3)
将邻二羟基炔烃类化合物b(50mg,0.27mmol),加入到搅拌的正庚烷中(1mL),随后依次加入三苯基磷氯化金(6.7mg,0.014mol)和三氟甲烷磺酸银(3.6mg,0.014mol)在80℃下反应1小时后加入苯胺(75ul,0.81mmol)，继续在80℃体系中反应5小时。在旋转蒸发仪上抽干溶剂，经柱层析得到浅褐色的油状液体(38.7mg，59％)。
产物检测数据如下：
1H NMR(400MHz,CDCl3):δ＝7.31-7.23(m,2H),7.25–7.01(m,8H),6.25(s,1H),2.75-2.70(m,4H),2.48–2.32(m,2H)；13C NMR(100MHz,CDCl3):δ＝141.11,139.88,136.75,133.69,128.86,127.99,127.83,127.02,126.15,125.91,125.66,105.68,28.45,25.99,25.63。
Claims (4)
1.一种金催化的1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物的合成方法，其特征为邻二羟基炔烃类化合物、三苯基磷氯化金和三氟甲烷磺酸银依次加入有机溶剂中，加热条件反应1小时候后再加入胺继续反应，得到1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物，反应式如下:
其中R1为叔丁基，苯基，4-甲氧基苯基，4-甲基苯基；R2为苯基，氢；R3为氢，乙基，丙基，丁基，异丁基，环丙基，环己基，苯基，苄基，邻氯苯基，对氯苯基，对溴苯基，对硝基苯基，对甲氧基苄基，3-甲氧基丙基，炔丙基。
2.根据权利要求书1所述的一种金催化的1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物的合成方法，其特征是所用的有机溶剂选自：正庚烷、正己烷、环己烷、正壬烷、甲苯、四氢呋喃的一种或几种。
3.根据权利要求书1所述的一种金催化的1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物的合成方法，其特征是所加热的温度为60-120℃，维持时间为4-10小时。
4.根据权利要求书1所述的一种金催化的1,2,5-三取代1,4,5,6-四氢-环戊烷并[b]吡咯类化合物的合成方法，其特征是反应中各物质的物质的量比为：邻二羟基炔烃类化合物：三苯基磷氯化金：三氟甲烷磺酸银：胺：溶剂＝1:0.05-0.20:0.05-0.20:2-5:10-100。
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| CN107496419B (zh) * | 2016-06-14 | 2021-03-23 | 兰州大学 | 一种具有抗炎活性的环戊烷并[b]吡咯类化合物 |
| CN107129479B (zh) * | 2017-06-06 | 2019-08-30 | 五邑大学 | 一种环烷基并[b]呋喃类化合物的合成方法 |
| CN112094218B (zh) * | 2020-09-04 | 2024-01-26 | 湖北科技学院 | 一种吡咯类衍生物的合成方法 |
| CN113004294B (zh) * | 2021-03-08 | 2023-01-17 | 温州大学新材料与产业技术研究院 | 一种四氢呋喃并1,4-二氢喹啉类化合物及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1955163A (zh) * | 2005-10-28 | 2007-05-02 | 中国人民解放军军事医学科学院毒物药物研究所 | 环氧合酶－2选择性抑制剂及其医药用途 |
| WO2012136772A1 (en) * | 2011-04-07 | 2012-10-11 | Karo Bio Ab | Fused pyrrole derivates as estrogen receptor ligands |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1955163A (zh) * | 2005-10-28 | 2007-05-02 | 中国人民解放军军事医学科学院毒物药物研究所 | 环氧合酶－2选择性抑制剂及其医药用途 |
| WO2012136772A1 (en) * | 2011-04-07 | 2012-10-11 | Karo Bio Ab | Fused pyrrole derivates as estrogen receptor ligands |
Non-Patent Citations (5)
| Title |
|---|
| Addition von Aldehyden an aktivierte Doppelbindungen, XXXIV Addition von Aldehyden an cyclische a-Methylenketone;Hermann Stetter等;《Chemische Berichte》;19841231;第117卷(第2期);第682-693页 |
| Enone-Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles;Benjamin B. Thompson等;《ORGANIC LETTERS》;20110609;第13卷(第13期);第3289-3291页 |
| Organocatalytic Asymmetric Vinylogous r-Ketol Rearrangement:Enantioselective Construction of Chiral All-Carbon Quaternary Stereocenters in Spirocyclic Diketones via Semipinacol-Type 1,2-Carbon Migration;En Zhang等;《Journal of the American Chemical Society》;20090928;第131卷;第14626-14627页 |
| Rube＇n S. Ramo＇n等.[(NHC)AuCl]-catalyzed Meyer–Schuster rearrangement: scope and limitations.《Tetrahedron》.2008,第65卷第1767-1773页. |
| Umlagerung tertisrer Athinyl-carbinole in ungesiittigte Ketone;Kurt H. Meyer等;《Chemische Berichte》;19221231;第55卷;第819-823页 |
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| CN106278993A (zh) | 2017-01-04 |
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