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Synthesis of Substituted Pyrazoles from Aryl-Sydnones.

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BACKGROUND In this current work, a new synthesis strategy was developed to obtain 1,3,4-trisubstituted pyrazoles derivatives. METHODS A series of 1,3,4-trisubstituted pyrazoles have been prepared via 1,3-dipolar cycloaddition reaction of… Click to show full abstract

BACKGROUND In this current work, a new synthesis strategy was developed to obtain 1,3,4-trisubstituted pyrazoles derivatives. METHODS A series of 1,3,4-trisubstituted pyrazoles have been prepared via 1,3-dipolar cycloaddition reaction of 3-phenylsydnones with a variety of alkenes derivatives, symmetric and non-symmetric alkynes derivatives, N-phenyl-maleimide, N-benzyl-maleimides and maleic anhydride under conventional manner. RESULTS Moreover, in this work it has been demonstrated that the 4-bromopyrazole intermediates can be further functionalized by a combination of Suzuki-Miyaura cross coupling reactions with aryl-boronic acids and N-arylation reactions of anilines. CONCLUSION In summary, we have developed a new method to obtain 1,3,4 triarylated pyrazoles through 3-phenylsydnone 1,3-dipolar cycloadditions. By comparing the different reactions, it is apparent that high temperatures and xylene as solvent are key to achieve pyrazoles derivatives and the best yields were observed for symmetric and non-symmetric alkynes as dipolarophiles.

Keywords: pyrazoles aryl; synthesis substituted; synthesis; substituted pyrazoles; aryl sydnones

Journal Title: Current organic synthesis
Year Published: 2022

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