Regioselective Synthesis of 1,3,5-Tri- and 1,3,4,5-Tetrasubstituted Pyrazoles from N-Arylhydrazones and Nitroolefins

• Abstract
• Full Text HTML
• Hi-Res PDF[134 KB]
• PDF w/ Links[183 KB]

• Supporting Info
• Figures
• Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

• PDF/HTML,
  figures/images,
  references and tables,
  (where available)

Abstract

Two general protocols are developed for the regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles by the reaction of electron-deficient N-arylhydrazones with nitroolefins. Studies on the stereochemistry of the key pyrazolidine intermediate suggest a stepwise cycloaddition mechanism.

Citing Articles

View all 11 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 10 ACS Journal articles (5 most recent appear below).

• 

  Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases

  Bassam Abu Thaher, Martina Arnsmann, Frank Totzke, Jan E. Ehlert, Michael H. G. Kubbutat, Christoph Schächtele, Markus O. Zimmermann, Pierre Koch, Frank M. Boeckler, and Stefan A. Laufer
  Journal of Medicinal Chemistry2012 55 (2), 961-965

  • Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases

    Bassam Abu Thaher, Martina Arnsmann, Frank Totzke, Jan E. Ehlert, Michael H. G. Kubbutat, Christoph Schächtele, Markus O. Zimmermann, Pierre Koch, Frank M. Boeckler, and Stefan A. Laufer
    Journal of Medicinal Chemistry2012 55 (2), 961-965

    In the course of searching for new p38α MAP kinase inhibitors, we found that the regioisomeric switch from 3-(4-fluorophenyl)-4-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine to 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine led to an almost ...

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

  Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones

  Metin Zora and Arif Kivrak
  The Journal of Organic Chemistry2011 76 (22), 9379-9390

  • Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones

    Metin Zora and Arif Kivrak
    The Journal of Organic Chemistry2011 76 (22), 9379-9390

    Synthesis of pyrazoles via electrophilic cyclization of α,β-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, α,β-alkynic hydrazones, prepared readily from ...

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

  From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles

  Santos Fustero, María Sánchez-Roselló, Pablo Barrio, and Antonio Simón-Fuentes
  Chemical Reviews2011 111 (11), 6984-7034

  • From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles

    Santos Fustero, María Sánchez-Roselló, Pablo Barrio, and Antonio Simón-Fuentes
    Chemical Reviews2011 111 (11), 6984-7034
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Synthesis of Pyrazoles via Electrophilic Cyclization

  Metin Zora, Arif Kivrak, and Ceyda Yazici
  The Journal of Organic Chemistry2011 76 (16), 6726-6742

  • Synthesis of Pyrazoles via Electrophilic Cyclization

    Metin Zora, Arif Kivrak, and Ceyda Yazici
    The Journal of Organic Chemistry2011 76 (16), 6726-6742

    Electrophilic cyclizations of α,β-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. α,β-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated ...

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

  Microwave-Assisted and Continuous Flow Multistep Synthesis of 4-(Pyrazol-1-yl)carboxanilides

  David Obermayer, Toma N. Glasnov, and C. Oliver Kappe
  The Journal of Organic Chemistry2011 76 (16), 6657-6669

  • Microwave-Assisted and Continuous Flow Multistep Synthesis of 4-(Pyrazol-1-yl)carboxanilides

    David Obermayer, Toma N. Glasnov, and C. Oliver Kappe
    The Journal of Organic Chemistry2011 76 (16), 6657-6669

    A series of 4-(pyrazol-1-yl)carboxanilides active as inhibitors of canonical transient receptor potential channels were synthesized in an efficient three-step protocol using controlled microwave heating. The general synthetic strategy involves ...

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

SciFinder Links

• Get Reference Detail
• Get Substances
• Get Reactions
• Get Cited
• Get Citing