CN115043768A - 一种酸促进环丙基开环合成n-芳基吡咯烷-2-酮的方法 - Google Patents
一种酸促进环丙基开环合成n-芳基吡咯烷-2-酮的方法 Download PDFInfo
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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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
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Abstract
本发明提供了一种酸促进环丙基开环合成N‑芳基吡咯烷‑2‑酮的方法,属于有机合成领域,该方法使用N‑芳基环丙烷甲脒与酰氯作为底物,于110‑130℃下,在HCl气体氛围中反应6‑24h,无需催化剂或其他反应添加剂即可通过环丙基开环再环化过程生成N‑芳基吡咯烷‑2‑酮。本发明专利的合成方法仅使用廉价的分子筛作提供干燥的反应环境,无需金属催化剂和配体便可在温和的条件下使环丙基开环,相较于以往的合成方法,本发明方法所用的脒类化合物和酰氯类衍生物廉价易得,条件温和,反应具有良好的区域选择性和收率,且具有宽泛的官能团容忍性,合成步骤简单、反应条件温和、操作简单易行、反应产率高达88%,反应底物廉价易得,所适用的底物范围广泛。
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法。
背景技术
环丙烷由于其较大的环张力,可以在释放应变能(27.5kcal/mol)的协助下开环,因而其经常作为C3砌块用于合成其他环化合物。经过多年的发展,已经发展出许多诱导环丙基开环的方法,如:金属催化剂催化的D-A型环丙烷开环,该类环丙烷底物C-C键一端为吸电子基,另一端为给电子基,通过取代基的电子特性差异来活化环丙烷C-C键促进开环反应的发生;金属介导、金属催化的环丙烯开环反应,烯丙基的存在可以活化环丙烷;环丙胺类化合物也发展出了许多热重排开环,过渡金属催化开环,自由基开环策略,使用六水合三氯化钪和手性N,N’-二氧化物的络合物在1,2,-二氯乙烷中催化邻苯二胺和环丙基酮通过高效不对称开环/环化/逆曼尼希反应合成了手性苯并咪唑衍生物,反应条件温和且具有较宽的底物范围,收率高达99%(Xia,Y.et al.Angew.Chem.Int.Ed.Engl.2016,55,12228-12232)。
现有的镍催化的环丙基醛亚胺和烯酮的[3+2]环加成反应通过使用Ni(cod)2作为催化剂,使用氮杂环卡宾配体在叔丁醇钛和叔丁醇钾的辅助下获得了三取代的环戊烷,该方法能够合成一些环丙基酮无法合成的底物(Liu,L.et al.Org.Lett.,2007,9,3885-3887)。
其后通过金催化的带有环丙基的氧杂链状1,7-烯炔的开环环化反应,反应使用IPrAuNTf2作为催化剂在二氯甲烷中于室温下进行便可以以中等至良好的反应收率获得多取代的呋喃衍生物(Zang,W.et al.Chem.Commun.(Camb),2019,55,8126-8129)。
发明内容
本发明提供了以脒为诱导基团促进环丙烷开环的新思路,在该基团的诱导下,反应仅需要使用廉价HCl即可促进环丙烷开环,在分子筛作为干燥剂提供的干燥溶剂环境中,便可在酸性环境下进行区域选择性的环丙烷开环反应,合成N-芳基吡咯烷-2-酮。
本发明采用以下技术方案:
反应结束后,回至室温,旋蒸除去有机溶剂。之后,所得粗品柱层析纯化,得到最终产物N-芳基吡咯烷-2-酮。
根据上述的使用酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,反应中所述N-芳基环丙烷甲脒具有以下通式:
通式中为R1为芳基和稠环芳基中的任意一种。
根据上述的酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,反应中所述酰氯具有以下通式:
通式中为R2为芳基。
根据上述的酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,所述反应产物N-芳基吡咯烷-2-酮衍生物具有以下通式:
通式中为R为芳基、杂芳基和稠环芳基中的任意一种。
根据上述的酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,反应中所述酰氯的用量为N-芳基环丙烷甲脒摩尔量的1-2当量。
根据上述的酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,反应中所述溶剂为二甲苯或甲苯。
根据上述的酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,反应中所述反应温度为110-130℃,反应时间为6-24h。
根据上述的酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,反应中所述反应气氛为HCl气体。
有益效果:
附图说明
图1是实施例1制备的N-苯基吡咯烷-2-酮的1H NMR谱图;
图2是实施例1制备的N-苯基吡咯烷-2-酮的13CNMR谱图;
图3是制备的N-(4-氯苯基)吡咯烷-2-酮的1H NMR谱图;
图4是制备的N-(4-氯苯基)吡咯烷-2-酮的13C NMR谱图;
图5是制备的N-(4-溴苯基)吡咯烷-2-酮的1H NMR谱图;
图6是制备的N-(4-溴苯基)吡咯烷-2-酮的13C NMR谱图;
图7是制备的N-(3-溴苯基)吡咯烷-2-酮的1H NMR谱图;
图8是制备的N-(3-溴苯基)吡咯烷-2-酮的13C NMR谱图;
图9是制备的N-(4-氟苯基)吡咯烷-2-酮的1H NMR谱图;
图10是制备的N-(4-氟苯基)吡咯烷-2-酮的13C NMR谱图;
图11是制备的N-(4-硝基苯基)吡咯烷-2-酮的1H NMR谱图;
图12是制备的N-(4-硝基苯基)吡咯烷-2-酮的13C NMR谱图;
图13是制备的N-(4-甲基苯基)吡咯烷-2-酮的1H NMR谱图;
图14是制备的N-(4-甲基苯基)吡咯烷-2-酮的13C NMR谱图;
图15是制备的N-(4-甲氧基苯基)吡咯烷-2-酮的1H NMR谱图;
图16是制备的N-(4-甲氧基苯基)吡咯烷-2-酮的13C NMR谱图;
图17是制备的N-(1-萘基)吡咯烷-2-酮的1H NMR谱图;
图18是制备的N-(1-萘基)吡咯烷-2-酮的13C NMR谱图;
具体实施方式
为了对本发明进行更好地说明,现举实施例如下:
实施例1
结构式如下的N-苯基吡咯烷-2-酮的制备方法:
向25ml反应管中加入底物N-苯基环丙烷甲脒16.0mg(0.1mmol),分子筛240mg,二甲苯1.5mL,随后加入苯甲酰氯(0.15mmol),加入磁子并封口,置换一次干燥的HCl气体后置于130℃油浴中搅拌反应12h。反应结束后,加入1mL 1M HCl溶液水解亚胺中间体,水解完成后使用DCM萃取水相三次,浓缩有机相得粗品,粗品经过柱层析分离纯化即可得到目标产物13.4mg,收率83%。目标产物表征数据:White solid(13.3mg,83%yield)(hexane/EtOAc=2:1as an eluent).Mp:65-66℃.1H NMR(400MHz,CDCl3)δ7.64–7.58(m,2H),7.40–7.34(m,2H),7.18–7.11(m,1H),3.87(t,J=7.0Hz,2H),2.62(t,J=8.1Hz,2H),2.16(p,J=7.5Hz,2H).13C NMR(100MHz,CDCl3)δ174.22,139.42,128.83,124.51,119.97,48.80,32.77,18.05.LRMS(EI):m/z calcd for C10H11NO[M]+,161.08;found,161.00。
Claims (9)
5.一种酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,其特征在于:所述酰氯的用量为N-芳基环丙烷甲脒摩尔量的1-2当量。
6.一种酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,其特征在于:所述溶剂为二甲苯或甲苯。
8.一种酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,其特征在于:所述反应温度为110-130℃,反应时长为6-24h。
9.一种酸促进环丙基开环合成N-芳基吡咯烷-2-酮的方法,其特征在于:所述反应气氛为HCl气体。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1161040A (zh) * | 1994-10-20 | 1997-10-01 | 美国辉瑞有限公司 | 二环四氢吡唑吡啶和其作为药物的应用 |
CN101481369A (zh) * | 2009-03-04 | 2009-07-15 | 中国科学院上海有机化学研究所 | 一种合成4,6位取代3,-4-二氢-吡喃-2-酮衍生物的方法 |
WO2018233633A1 (zh) * | 2017-06-20 | 2018-12-27 | 南京明德新药研发股份有限公司 | Ssao 抑制剂 |
CN110003110A (zh) * | 2019-04-29 | 2019-07-12 | 南京工业大学 | 一种芳基β-氨基酮化合物及其制备方法 |
CN113185521A (zh) * | 2021-05-08 | 2021-07-30 | 新乡市润宇新材料科技有限公司 | 一种环丙基开环制备四氢吡咯并[1,2-a]1,3,5-三嗪-4-酮类化合物的方法 |
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- 2022-06-20 CN CN202210698491.6A patent/CN115043768A/zh active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1161040A (zh) * | 1994-10-20 | 1997-10-01 | 美国辉瑞有限公司 | 二环四氢吡唑吡啶和其作为药物的应用 |
CN101481369A (zh) * | 2009-03-04 | 2009-07-15 | 中国科学院上海有机化学研究所 | 一种合成4,6位取代3,-4-二氢-吡喃-2-酮衍生物的方法 |
WO2018233633A1 (zh) * | 2017-06-20 | 2018-12-27 | 南京明德新药研发股份有限公司 | Ssao 抑制剂 |
CN110003110A (zh) * | 2019-04-29 | 2019-07-12 | 南京工业大学 | 一种芳基β-氨基酮化合物及其制备方法 |
CN113185521A (zh) * | 2021-05-08 | 2021-07-30 | 新乡市润宇新材料科技有限公司 | 一种环丙基开环制备四氢吡咯并[1,2-a]1,3,5-三嗪-4-酮类化合物的方法 |
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