A Facile Synthesis of 2-Methylquinolines via Pd-Catalyzed Aza-Wacker Oxidative Cyclization

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Abstract

A novel Pd-catalyzed Wacker-type oxidative cyclization under air is described. By using this cyclization, a series of 2-methylquinolines are readily prepared with good yields under mild conditions.

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This article has been cited by 13 ACS Journal articles (5 most recent appear below).

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  Regioselective Pd-Catalyzed Aerobic Aza-Wacker Cyclization for Preparation of Isoindolinones and Isoquinolin-1(2H)-ones

  Guoqiang Yang and Wanbin Zhang
  Organic Letters2012 14 (1), 268-271

  • Regioselective Pd-Catalyzed Aerobic Aza-Wacker Cyclization for Preparation of Isoindolinones and Isoquinolin-1(2H)-ones

    Guoqiang Yang and Wanbin Zhang
    Organic Letters2012 14 (1), 268-271

    A switchable regioselective intramolecular aerobic aza-Wacker cyclization catalyzed by palladium is presented. Isoindolinones or isoquinolin-1(2H)-ones could be prepared selectively from the same substrates using different catalysts. The type and steric ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A Facile Synthesis of Substituted 2-Alkylquinolines through [3 + 3] Annulation between 3-Ethoxycyclobutanones and Aromatic Amines at Room Temperature

  Gang Shan, Xiuyun Sun, Qian Xia, and Yu Rao
  Organic Letters2011 13 (21), 5770-5773

  • A Facile Synthesis of Substituted 2-Alkylquinolines through [3 + 3] Annulation between 3-Ethoxycyclobutanones and Aromatic Amines at Room Temperature

    Gang Shan, Xiuyun Sun, Qian Xia, and Yu Rao
    Organic Letters2011 13 (21), 5770-5773

    An efficient single-step approach toward the synthesis of 2-alkylquinolines is described. Through a Lewis acid mediated [3 + 3] annulation reaction between 3-ethoxycyclobutanones and aromatic amines, a variety of multisubstituted 2-alkylquinoline ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines

  Shaukat Ali, Hai-Tao Zhu, Xiao-Feng Xia, Ke-Gong Ji, Yan-Fang Yang, Xian-Rong Song, and Yong-Min Liang
  Organic Letters2011 Article ASAP

  • Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines

    Shaukat Ali, Hai-Tao Zhu, Xiao-Feng Xia, Ke-Gong Ji, Yan-Fang Yang, Xian-Rong Song, and Yong-Min Liang
    Organic Letters2011 Article ASAP

    Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties can be synthesized in moderate to excellent yields (up to 99%) by 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine (I2) under mild ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Zn(OTf)₂-Catalyzed Reactions of Ethenetricarboxylates with 2-Aminobenzaldehydes Leading to Tetrahydroquinoline Derivatives

  Shoko Yamazaki, Masachika Takebayashi and Kazuya Miyazaki
  The Journal of Organic Chemistry2010 75 (4), 1188-1196

  • Zn(OTf)₂-Catalyzed Reactions of Ethenetricarboxylates with 2-Aminobenzaldehydes Leading to Tetrahydroquinoline Derivatives

    Shoko Yamazaki, Masachika Takebayashi and Kazuya Miyazaki
    The Journal of Organic Chemistry2010 75 (4), 1188-1196

    Quinolines are an important class of compounds, and the development of new efficient synthetic strategies for the construction of quinolines is of considerable interest. Zinc triflate catalyzed cyclization of ethenetricarboxylate derivatives with 2-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of Benzimidoyl Chlorides with 1,6-Enynes and Cyclization To Synthesize Quinoline Derivatives

  Guo-Lin Gao, Yan-Ning Niu, Ze-Yi Yan, Hong-Li Wang, Gang-Wei Wang, Ali Shaukat and Yong-Min Liang
  The Journal of Organic Chemistry2010 75 (4), 1305-1308

  • Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of Benzimidoyl Chlorides with 1,6-Enynes and Cyclization To Synthesize Quinoline Derivatives

    Guo-Lin Gao, Yan-Ning Niu, Ze-Yi Yan, Hong-Li Wang, Gang-Wei Wang, Ali Shaukat and Yong-Min Liang
    The Journal of Organic Chemistry2010 75 (4), 1305-1308

    A domino reaction via palladium-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and then cyclization to form quinoline derivatives has been developed. The reaction conditions and the scope of the process are examined, and a ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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