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Efficient Synthesis of New Pyrazoles Derivatives via Functionalized Aryl-Sydnones
* 1 , 2 , 3 , 4 , 4 , 4 , 5
1  PhD student
2  Docteur
3  Professor at the University Ibn Zohr Agadir, Morocco. Laboratoire de Chimie Organique, Organométallique et Valorisation des Substances Naturelles. Faculté des Sciences Agadir, BP 8106, Cité Dakhla Agadir 80000, Université Ibn Zohr, Maroc
4  Professor at the University Sultan Moulay Slimane, Beni Mellal, Morocco. Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, BP 523, 23000 Béni-Mellal, Morocco.
5  Professor at the University de Barcelona, Faculty of Pharmacy and Food Science, Spain. Laboratori de Quı́mica Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal 643, E-08028 Barcelona, Spain.

Abstract:

Pyrazoles are a privileged class of heteroaromatic compounds and they represent the core motif,1 in heterocyclic chemistry.2

The presence of the pyrazole nucleus in several structures leads to diversified applications in different areas such as technology, medicine and agriculture. In particular, they are described as inhibitors of protein glycation, antibacterial, antifungal, anticancer, antidepressant, anti-inflammatory, anti-tuberculosis, antioxidant as well as antiviral agents.3

Our contribution in the development of pyrazole derivatives synthesis has been to develop a new method of synthesis of the substituted pyrazole skeleton from the sydnone. Sydnones are considered among the most known mesoionic compounds studied for cycloaddition reactions with alkynes. In this work, a methodology for the 3 + 2 cycloaddition between sydnones and symmetric and non-symmetric alkynes has been developed.

References

  1. (a) A. W. Brown, J. P. A. Harrity. Tetrahedron. 2017, 73, 3160; (b) A. Ansari, A. Ali, M. Asif. New J. Chem. 2017, 41, 16; (c) C. Lamberth. Heterocycles. 2007, 71, 1467.
  2. L. Browne, J. F. Vivat, A. Plant, E. G. Bengoa, J. P. A. Harrity. J. Am. Chem. Soc. 2009, 131, 7762.
  3. (a) K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y. N. Mabkhot, F. A. Al-aizari and M. Ansar. Molecules. 2018, 23, 134; (b) S. Fustero, M. S. Roselló, P. Barrio, A. S. Fuentes. Rev. 2011, 111, 6984; (c) A. Ansari, A. Ali, M. Asif. New J. Chem. 2017, 41, 16.
Keywords: sydnone; pyrazole; 1,3-dipolar cycloaddition; C-arylation; Suzuki-Miyaura cross-coupling reactions; microwave; N-heterocycle; N-arylations reactions; aryl halides
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