InBr₃-Promoted Divergent Approach to Polysubstituted Indoles and Quinolines from 2-Ethynylanilines: Switch from an Intramolecular Cyclization to an Intermolecular Dimerization by a Type of Terminal Substituent Group

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Abstract

Use of a 2-ethynylaniline having an alkyl or aryl group on the terminal alkyne selectively produced a variety of polyfunctionalized indole derivatives in moderate to excellent yields via indium-catalyzed intramolecular cyclization of the corresponding alkynylaniline. In contrast, employment of a substrate with a trimethylsilyl group or with no substituent group on the terminal triple bond, exclusively afforded polysubstituted quinoline derivatives in good yields via indium-promoted intermolecular dimerization of the ethynylaniline. This indium catalytic system successfully accommodated the intramolecular cyclization of other arylalkyne skeletons involving a carboxylic acid and an amide group.

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This article has been cited by 15 ACS Journal articles (5 most recent appear below).

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  Copper-Catalyzed [5 + 1] Annulation of 2-Ethynylanilines with an N,O-Acetal Leading to Construction of Quinoline Derivatives

  Norio Sakai, Kosuke Tamura, Kazuyori Shimamura, Reiko Ikeda, and Takeo Konakahara
  Organic Letters2012 14 (3), 836-839

  • Copper-Catalyzed [5 + 1] Annulation of 2-Ethynylanilines with an N,O-Acetal Leading to Construction of Quinoline Derivatives

    Norio Sakai, Kosuke Tamura, Kazuyori Shimamura, Reiko Ikeda, and Takeo Konakahara
    Organic Letters2012 14 (3), 836-839

    A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a C1 part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2 and ...

    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
• 

  Palladium-Catalyzed Highly Regio- and Stereoselective Synthesis of 4-Alkylidene-4H-3,1-benzoxazines from N-Acyl-o-alkynylanilines

  Takao Saito, Shohei Ogawa, Naoya Takei, Noriki Kutsumura, and Takashi Otani
  Organic Letters2011 13 (5), 1098-1101

  • Palladium-Catalyzed Highly Regio- and Stereoselective Synthesis of 4-Alkylidene-4H-3,1-benzoxazines from N-Acyl-o-alkynylanilines

    Takao Saito, Shohei Ogawa, Naoya Takei, Noriki Kutsumura, and Takashi Otani
    Organic Letters2011 13 (5), 1098-1101

    The highly regio- and stereoselective 6-exo-dig mode cyclization of N-acyl-o-alkynylanilines producing 4-alkylidene-3,1-benzoxazines occurred unpredictably by use of a proper catalyst [Pd(OAc)2] and an effective additive (acetic acid) under suitable ...

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

  Platinum-Catalyzed, One-Pot Tandem Synthesis of Indoles and Isoquinolines via Sequential Rearrangement of Amides and Aminocyclization

  Noriko Okamoto, Kei Takeda, and Reiko Yanada
  The Journal of Organic Chemistry2010 75 (22), 7615-7625

  • Platinum-Catalyzed, One-Pot Tandem Synthesis of Indoles and Isoquinolines via Sequential Rearrangement of Amides and Aminocyclization

    Noriko Okamoto, Kei Takeda, and Reiko Yanada
    The Journal of Organic Chemistry2010 75 (22), 7615-7625

    By using platinum(II) chloride as a Lewis acid catalyst, concise and efficient syntheses of indole carbamates, 1,2-dihydroisoquinoline carbamates, macrocyclic indole carbamates, indole ureas, and indole phosphoranes have been achieved via tandem Hofmann-...

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

  Enantioselective Synthesis of Indole-Fused Dihydropyranones via Catalytic Cycloaddition of Ketenes and 3-Alkylenyloxindoles

  Hui Lv, Xiang-Yu Chen, Li-hui Sun, and Song Ye
  The Journal of Organic Chemistry2010 75 (20), 6973-6976

  • Enantioselective Synthesis of Indole-Fused Dihydropyranones via Catalytic Cycloaddition of Ketenes and 3-Alkylenyloxindoles

    Hui Lv, Xiang-Yu Chen, Li-hui Sun, and Song Ye
    The Journal of Organic Chemistry2010 75 (20), 6973-6976

    Chiral N-heterocyclic carbenes were found to be efficient catalysts for the formal [4+2] cycloaddition reaction of alkyl(aryl)ketenes and 3-alkylenyloxindoles to give the corresponding 3,4-dihydropyrano[2,3-b]indol-2-ones in excellent yields with good ...

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

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