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Current Medicinal Chemistry

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ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

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Review Article

Sydnone: Synthesis, Reactivity and Biological Activities

Author(s): Souad Zerbib, Mostafa Khouili, Marco Catto* and Latifa Bouissane*

Volume 30, Issue 10, 2023

Published on: 03 October, 2022

Page: [1122 - 1144] Pages: 23

DOI: 10.2174/0929867329666220620123050

Price: $65

Abstract

Sydnones are among the most well-known mesoionic compounds. Since their synthesis in 1935 by Earl and Mecknay, numerous researches have shown that the chemical behavior, physical and biological properties of sydnones make them the most useful compounds in organic chemistry. Sydnones undergo thermal 1,3-dipolar cycloaddition reaction with dipolarophiles (alkynes or alkenes) to give exclusively derivatives containing a pyrazole moiety exhibiting numerous applications, such as pharmaceuticals and agrochemicals. However, the sydnone cycloaddition reaction with alkynes requires harsh conditions, like high temperatures and long reaction times, giving poor regioselectivity to the resulting products. To overcome these constraints, new reactions named CuSAC (Copper- Catalyzed Sydnone-Alkyne Cycloaddition) and SPSAC (Strain-Promoted Sydnone- Alkyne Cycloaddition) have been developed, leading to pyrazoles with interesting constant kinetics.

Keywords: Sydnone, mesoionic, heterocycles, functionalization, 1, 3-dipolar cycloaddition, biorthogonal reaction, biological activities, applications.

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