Transition Metal-Catalyzed Synthesis of Pyrroles from Dienyl Azides

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Abstract

A range of 2,5-disubstituted and 2,4,5-trisubstituted pyrroles can be synthesized from dienyl azides at room temperature using catalytic amounts of ZnI₂ or Rh₂(O₂CC₃F₇)₄.

Citing Articles

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This article has been cited by 17 ACS Journal articles (5 most recent appear below).

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  Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones

  Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen Wang
  Organic Letters2011 13 (24), 6362-6365

  • Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones

    Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen Wang
    Organic Letters2011 13 (24), 6362-6365

    A highly efficient and convenient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles from readily accessible 2-azido acrylates and nitrones has been developed. This reaction proceeded under mild conditions without the assistance of any metal, ...

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

  Regioselective Synthesis of 2,3,4- or 2,3,5-Trisubstituted Pyrroles via [3,3] or [1,3] Rearrangements of O-Vinyl Oximes

  Heng-Yen Wang, Daniel S. Mueller, Rachna M. Sachwani, Rachel Kapadia, Hannah N. Londino, and Laura L. Anderson
  The Journal of Organic Chemistry2011 76 (9), 3203-3221

  • Regioselective Synthesis of 2,3,4- or 2,3,5-Trisubstituted Pyrroles via [3,3] or [1,3] Rearrangements of O-Vinyl Oximes

    Heng-Yen Wang, Daniel S. Mueller, Rachna M. Sachwani, Rachel Kapadia, Hannah N. Londino, and Laura L. Anderson
    The Journal of Organic Chemistry2011 76 (9), 3203-3221

    The regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles has been achieved via [3,3] and [1,3] sigmatropic rearrangements of O-vinyl oximes, respectively. Iridium-catalyzed isomerization of easily prepared O-allyl oximes enables rapid ...

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

  Ruthenium-Catalyzed γ-Carbolinium Ion Formation from Aryl Azides; Synthesis of Dimebolin

  Huijun Dong, Regina T. Latka, and Tom G. Driver
  Organic Letters2011 Article ASAP

  • Ruthenium-Catalyzed γ-Carbolinium Ion Formation from Aryl Azides; Synthesis of Dimebolin

    Huijun Dong, Regina T. Latka, and Tom G. Driver
    Organic Letters2011 Article ASAP

    A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize ...

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

  One-Pot Synthesis of Pyrrolo[3,2-d]pyridazines and Pyrrole-2,3-diones via Zirconocene-Mediated Four-Component Coupling of Si-Tethered Diyne, Nitriles, and Azide

  Shaoguang Zhang, Jing Zhao, Wen-Xiong Zhang, and Zhenfeng Xi
  Organic Letters2011 13 (7), 1626-1629

  • One-Pot Synthesis of Pyrrolo[3,2-d]pyridazines and Pyrrole-2,3-diones via Zirconocene-Mediated Four-Component Coupling of Si-Tethered Diyne, Nitriles, and Azide

    Shaoguang Zhang, Jing Zhao, Wen-Xiong Zhang, and Zhenfeng Xi
    Organic Letters2011 13 (7), 1626-1629

    A one-pot synthesis of pyrrolo[3,2-d]pyridazine derivatives via zirconocene-mediated four-component coupling of one Si-tethered diyne, two nitriles, and one azide is reported. When TMSN3 was used, pyrrole-2,3-diones were formed in good yields. Further ...

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

  Enantioselective Organocatalytic Aza-Ene-Type Domino Reaction Leading to 1,4-Dihydropyridines

  Artur Noole, Maria Borissova, Margus Lopp, and Tõnis Kanger
  The Journal of Organic Chemistry2011 76 (6), 1538-1545

  • Enantioselective Organocatalytic Aza-Ene-Type Domino Reaction Leading to 1,4-Dihydropyridines

    Artur Noole, Maria Borissova, Margus Lopp, and Tõnis Kanger
    The Journal of Organic Chemistry2011 76 (6), 1538-1545

    A new general methodology was developed to access highly enantiomerically enriched 1,4-dihydropyridines (DHPs) 3 via an organocatalytic asymmetric aza-ene-type cascade reaction, cocatalyzed by (S)-diarylprolinol−TMS ether V and benzoic acid (BA). Both ...

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

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