1,2,4-Triazoles : Synthèses,

Réactivités et Activités
biologiques

Encadrant : Pr. Mohamed Lotfi Efrit

Elaborée par : Chachia Houria

Année Universitaire : 2023-2024

PLA N
 01 02
Introduction Laboratories
SOHeS

03 04
1,2,4-triazoles Strategies de
Structure et propriétés
synthèse
 05 06
Réactivité Activité biologique

07
Conclusion
 01
Introduction
 En 1883 4

2
1

1,2,4-Triazole
Hans von Pechmann
Première Synthèse des Clés dans la conception des Des nouvelles méthodes
1,2,4-Triazoles par Hans médicaments et d'agents de synthèse et activité
von Pechmann pharmaceutiques biologique

1883 1930 1980 2000 Années

Récentes

Développement des L'importance des triazoles

méthodes de synthèse comme : antibactériens,
plus efficace antifongiques et anticancéreux
 5,768

2,114

533
347

109

2000 2005 2009 2015 2020

L’Evolution de la Recherche sur les

Triazoles
1.États-Unis
2.Chine
3.Inde
4.Allemagne
5.Japon
6.Royaume-
Uni
7.France
8.Canada
 02
Laboratoires
SOHeS
 Laboratoire de Chimie
FST
Organique Sélective &
Hétérocyclique
Pr. Med Lotfi Efrit Nombre d’articles publié
 Selective Organic & Heterocylic Synthesis-Biological Activity Evaluation
LR17ES01
Synthèse de Molécules
Étude de l'Activité
Hétérocycliques
Biologique

Pharmacocinétique Recherche d'Effets

Pharmacologiques

Méthodes de
Caractérisation
Synthèse Organique
Structurale
Innovantes
En 2021
 03
1,2,4-triazoles
Structure et Propriétés
 1
5
NH

4 N N2
T°fusion = 140 à 160°C
3
T°ebulution = 300 à 320°C

1,2,4-triazole
Solubilité dans les Solvants

5% 65 % 75%
Eau Ethanol Chloroforme
Methanol Dichloro-méthane

Acetone
 8.27
13.5 1
5 NH

4 N N2

3
8.27
14 12 10 8 6 4 2 0
PPM

RMN’H
 03
Stratégie de
Synthèse
 A partir de l’Amidine
H3C O R N
O C N
O S
R O
O HN
H3C O
R NH H3C O CH3
C C S
H2 H2 O
R

NH2

O
R
N S R

NH O
N
N
 05
Réactivité
Substitution électrophile
 Réactions de substitution électrophile : Les 1,2,4-triazoles peuvent subir des
réactions de substitution électrophile, où un groupe électrophile se substitue à un
atome d'azote du cycle triazole. Cela permet la fonctionnalisation sélective du cycle
triazole pour introduire diverses fonctionnalités chimiques.
Réactions de cyclo addition
 Réactions de cycloaddition : Les 1,2,4-triazoles peuvent participer à des
réactions de cycloaddition, telles que la cycloaddition de Huisgen
(réaction "click") avec des azides pour former des 1,2,3-triazoles. Ces
réactions permettent la formation de liaisons carbone-azote
supplémentaires et l'expansion de la diversité chimique des 1,2,4-triazoles.
Réactions de réduction
Réactions de réduction : Les 1,2,4-triazoles peuvent être
réduits en utilisant divers agents réducteurs pour former
des dérivés d'1,2,4-triazoline. Cette réduction peut être
utile pour la préparation de produits intermédiaires ou
pour modifier les propriétés physicochimiques des 1,2,4-
triazoles.
 Réactions de couplage croisé
Réactions de couplage croisé : Les 1,2,4-triazoles peuvent être
utilisés comme substrats dans des réactions de couplage croisé
catalysées par des métaux, telles que les réactions de couplage de
Suzuki ou de Sonogashira. Ces réactions permettent la formation
de liaisons carbone-carbone entre les 1,2,4-triazoles et d'autres
composés organiques.
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