1-Methyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-Methyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-(1-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one；1-(1-methyl-3,4-dihydro-2H-quinolin-4-yl)pyrrolidin-2-one
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: IGIHGYKGRCPZCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Methyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到1-Methyl-4-(pyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines

  摘要：

  Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines 1 with N-vinyl-2-pyrrolidinone and with N-vinyl-N-methylacetamide give 4-(2-pyrrolidinon-1-yl)- and 4-(N-methylacetamido-N-yl)-1,2,3 ,4-tetrahydroquinolines (5 and 32), respectively. In a reaction with N-vinyl-2-pyrrolidinone, alpha-alkyl (11) and alpha-aryl(18) derivatives of 1 stereoselectively give cis-2,4-disubstituted tetrahydroquinolines 16 and 21, respectively. The 2-pyrrolidinon-1-yl and acetamido-N-yl substituents in the products are reduced with lithium aluminum hydride to the corresponding amino groups. Similar reactions of N-phenyl-1H-benzotriazole-1-methanamines 1 with 9-vinylcarbazole (40) lead to the corresponding 4-(carbazol-9-yl)-1,2,3,4-tetrahydroquinolines (41 and 42) and/or analogous 4-(benzotriazol-1-yl) or 4-(benzotriazol-2-yl) derivatives (37, 38, 43, and 44), depending on the nature of the starting material and the reaction conditions. By commencing with aniline derivatives in which the nitrogen atom is built into a heterocyclic system, this method allows for the addition of a another ring to the system, as exemplified by the conversion of phenothiazine into 46 and [3,1]benzoxazine into 49, 52, and 53.

  DOI：

  10.1021/jo00118a014
• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 N-甲基-N-苯基苯并三唑甲胺 在 对甲苯磺酸 作用下， 以90%的产率得到1-Methyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Additions of 1-(aminomethyl)benzotriazoles to enamines, enamides, and vinyl ethers: novel routes to 1,3-diamines and tetrahydroquinolines

  摘要：

  New methods for the synthesis of 1,3-diamines and of 4-substituted tetrahydroquinolines are described in which the key step is the addition of the condensation products derived from amines, aldehydes, and benzotriazole to enamines, enamides, and vinyl ethers.

  DOI：

  10.1021/jo00056a006

文献信息

• An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines­
  作者：Cristina Cimarelli、Samuele Bordi、Pamela Piermattei、Maura Pellei、Fabio Del Bello、Enrico Marcantoni

  DOI：10.1055/s-0036-1589104

  日期：2017.12

  is expanded to the one-pot synthesis of N-alkyltetrahydroquinolines through a very efficient iminium-Povarov approach. A deeper insight on the reaction system was provided by the study on the side reactions occurring in the reaction conditions and on the nature of the stereoselectivity. An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through

  摘要 描述了一种通过路易斯酸活化的Povarov反应一锅立体控制合成四氢喹啉的简便有效的合成方法。该方案利用了非常便宜，易于操作且环保的三氯化铈作为催化剂的优势，并允许在溶剂或无溶剂条件下进行反应，从而以良好的选择性获得最终四氢喹啉的反-或顺-异构体。 。反应范围扩大到一锅法合成N-烷基四氢喹啉通过非常有效的亚胺-Povarov方法。通过对在反应条件下发生的副反应和立体选择性的性质的研究，对反应体系有了更深入的了解。 描述了一种通过路易斯酸活化的Povarov反应一锅立体控制合成四氢喹啉的简便有效的合成方法。该方案利用了非常便宜，易于操作且环保的三氯化铈作为催化剂的优势，并允许在溶剂或无溶剂条件下进行反应，从而以良好的选择性获得最终四氢喹啉的反-或顺-异构体。 。反应范围扩大到一锅法合成N-烷基四氢喹啉通过非常有效的亚胺-Povarov方法。通过对在反应条件下发生的副反应和立体选择性的性质的研究，对反应体系有了更深入的了解。
• Electrochemical oxidative [4 + 2] annulation of tertiary anilines and alkenes for the synthesis of tetrahydroquinolines
  作者：Pengfei Huang、Pan Wang、Shengchun Wang、Shan Tang、Aiwen Lei

  DOI：10.1039/c8gc02463d

  日期：——

  pharmaceutical and agrochemical industries. The oxidative [4 + 2] annulation reaction provides a powerful tool for the rapid construction of six-membered heterocycles. Herein, we report a metal- and external oxidant-free method for the uniform synthesis of tetrahydroquinolines through the electrochemical oxidative [4 + 2] annulation of tertiary anilines and alkenes. In this strategy, one partner loses only

  杂环化合物，特别是氮杂环，是制药和农业化学工业中最重要的化合物类别之一。氧化[4 + 2]环化反应为六元杂环的快速构建提供了强大的工具。在这里，我们报告了通过叔苯胺和烯烃的电化学氧化[4 + 2]环化法均匀合成四氢喹啉的无金属和外部氧化剂的方法。在这种策略中，一个配偶体仅损失两个氢原子，而另一个配偶体则减少了一个不饱和度，并伴随着氢的产生。在细胞未分裂且室温下的条件下，以高收率制备了一系列四氢喹啉衍生物。
• Additions of 1-(aminomethyl)benzotriazoles to enamines, enamides, and vinyl ethers: novel routes to 1,3-diamines and tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00056a006

  日期：1993.2

  New methods for the synthesis of 1,3-diamines and of 4-substituted tetrahydroquinolines are described in which the key step is the addition of the condensation products derived from amines, aldehydes, and benzotriazole to enamines, enamides, and vinyl ethers.
• Dual C–H Functionalization of <i>N</i>-Aryl Amines: Synthesis of Polycyclic Amines via an Oxidative Povarov Approach
  作者：Chang Min、Abbas Sanchawala、Daniel Seidel

  DOI：10.1021/ol501073f

  日期：2014.5.16

  Iminium ions generated in situ via copper(I) bromide catalyzed oxidation of N-aryl amines readily undergo [4 + 2] cycloadditions with a range of dienophiles. This method involves the functionalization of both a C(sp(3))-H and a C(sp(2))-H bond and enables the rapid construction of polycyclic amines under relatively mild conditions.
• Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00118a014

  日期：1995.6

  Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines 1 with N-vinyl-2-pyrrolidinone and with N-vinyl-N-methylacetamide give 4-(2-pyrrolidinon-1-yl)- and 4-(N-methylacetamido-N-yl)-1,2,3 ,4-tetrahydroquinolines (5 and 32), respectively. In a reaction with N-vinyl-2-pyrrolidinone, alpha-alkyl (11) and alpha-aryl(18) derivatives of 1 stereoselectively give cis-2,4-disubstituted tetrahydroquinolines 16 and 21, respectively. The 2-pyrrolidinon-1-yl and acetamido-N-yl substituents in the products are reduced with lithium aluminum hydride to the corresponding amino groups. Similar reactions of N-phenyl-1H-benzotriazole-1-methanamines 1 with 9-vinylcarbazole (40) lead to the corresponding 4-(carbazol-9-yl)-1,2,3,4-tetrahydroquinolines (41 and 42) and/or analogous 4-(benzotriazol-1-yl) or 4-(benzotriazol-2-yl) derivatives (37, 38, 43, and 44), depending on the nature of the starting material and the reaction conditions. By commencing with aniline derivatives in which the nitrogen atom is built into a heterocyclic system, this method allows for the addition of a another ring to the system, as exemplified by the conversion of phenothiazine into 46 and [3,1]benzoxazine into 49, 52, and 53.