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Synthesis 2018; 50(08): 1675-1686
DOI: 10.1055/s-0036-1591752
DOI: 10.1055/s-0036-1591752
paper
An Efficient Synthesis of New 7-Trifluoromethyl-2,5-disubstituted Pyrazolo[1,5-a]pyrimidines
Badr Jismy
a
Laboratoire d’Infectiologie et Santé Publique (UMR 1282), Equipe Recherche et Innovation en Chimie Médicinale, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France Email: mohamed.abarbri@univ-tours.fr
b
Laboratoire de Chimie Physique et de Chimie Bioorganique, URAC 22, Université Hassan II de Casablanca, BP 146, 28800 Mohammedia, Maroc Email: akssira@yahoo.fr
,
Hassan Allouchi
a
Laboratoire d’Infectiologie et Santé Publique (UMR 1282), Equipe Recherche et Innovation en Chimie Médicinale, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France Email: mohamed.abarbri@univ-tours.fr
,
Gérald Guillaumet
c
Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans, UMR CNRS 7311, BP 6759, rue de Chartres, 45067 Orléans Cedex 2, France Email: gerald.guillaumet@univ-orleans.fr
,
Mohamed Akssira
b
Laboratoire de Chimie Physique et de Chimie Bioorganique, URAC 22, Université Hassan II de Casablanca, BP 146, 28800 Mohammedia, Maroc Email: akssira@yahoo.fr
,
Mohamed Abarbri*
a
Laboratoire d’Infectiologie et Santé Publique (UMR 1282), Equipe Recherche et Innovation en Chimie Médicinale, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France Email: mohamed.abarbri@univ-tours.fr
› Author Affiliations
Further Information
Publication History
Received: 25 October 2017
Accepted after revision: 13 December 2017
Publication Date:
22 January 2018 (online)
Abstract
A novel two-step synthesis of trifluoromethylated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines is reported from 3-aminopyrazoles and ethyl 4,4,4-trifluorobut-2-ynoate. The synthetic route begins with the one-pot synthesis of 7-trifluoromethylated pyrazolo[1,5-a]pyrimidin-5-ones by condensation of 3-aminopyrazoles with a fluorinated alkyne. The products obtained are used as building blocks to synthesize directly, with excellent yields via C–O bond activation, a library of new fluorinated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines of biological interest. This operation efficiently allows C–C, C–N and C–S bond formation.
Key words
fluorinated alkynes - 7-trifluoromethylated pyrazolo[1,5-a]pyrimidin-5-ones - C–O bond activation - trifluoromethylated pyrazolo[1,5-a]pyrimidines - biological interestSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591752.
- Supporting Information
-
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