In:
Current Organic Synthesis, Bentham Science Publishers Ltd., Vol. 20, No. 2 ( 2023-03), p. 246-257
Abstract:
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-benzylmaleimides,
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 crosscoupling 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 achieving
pyrazoles derivatives. The best yields were observed for symmetric and non-symmetric alkynes as dipolarophiles.
Type of Medium:
Online Resource
ISSN:
1570-1794
DOI:
10.2174/1570179419666220322121022
Language:
English
Publisher:
Bentham Science Publishers Ltd.
Publication Date:
2023
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