Jump to main content
Jump to site search
Publishing
Advanced

Issue 3, 2002
Previous Article Next Article

Regioselective acylation of 1-hydroxypyrazoles via metalated intermediates

Niels Østergaard,ab  Niels Skjærbæk,a  Mikael Begtrupb  and  Per Vedsø*b 
Author affiliations

* Corresponding authors

a ACADIA Pharmaceuticals A/S, Fabriksparken 58, Denmark
E-mail: ns@acadia-pharm.com
Fax: +45 43293030
Tel: +45 43293000

b The Royal Danish School of Pharmacy, Department of Medicinal Chemistry, Universitetsparken 2, Denmark
E-mail: pv@dfh.dk
Fax: +45 35306040
Tel: +45 35306487

Abstract

A range of C-4 and C-5 acylated 1-benzyloxypyrazoles (7a–e) and (4) have been prepared via Pd(0) catalysed cross-coupling between acid chlorides and 1-benzyloxy-4-(tributylstannyl)pyrazole (8) or 1-benzyloxypyrazol-5-ylzinc chloride. 3-Acylated 2-(4-methoxybenzyl)-2H-pyrazole 1-oxides (15a–f) were formed by reaction between the 3-magnesiated 2H-pyrazole 1-oxide (14) and acid chlorides. The benzyl group of 4 and 7a and the 4-methoxybenzyl (PMB) group of 15a were removed by treatment with conc. HCl or TFA in the presence of water, furnishing the corresponding C-acylated 1-hydroxypyrazoles.

Graphical abstract: Regioselective acylation of 1-hydroxypyrazoles via metalated intermediates

Back to tab navigation
Download options Please wait...

Publication details

The article was received on 05 Sep 2001, accepted on 26 Nov 2001 and first published on 03 Jan 2002


Article type: Paper
DOI: 10.1039/B107850J
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 428-433
  •   Request permissions

    Regioselective acylation of 1-hydroxypyrazoles via metalated intermediates

    N. Østergaard, N. Skjærbæk, M. Begtrup and P. Vedsø, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 428
    DOI: 10.1039/B107850J

    If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

    Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.
    • For reproduction of material from PCCP:
      Reproduced from Ref. XX with permission from the PCCP Owner Societies.
    • For reproduction of material from PPS:
      Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.
    • For reproduction of material from all other RSC journals and books:
      Reproduced from Ref. XX with permission from The Royal Society of Chemistry.

    If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

    In all cases the Ref. XX is the XXth reference in the list of references.

    If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC
    • For reproduction of material from PCCP:
      [Original citation] - Reproduced by permission of the PCCP Owner Societies
    • For reproduction of material from PPS:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
    • For reproduction of material from all other RSC journals:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry

    If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements