Chemistry of
1,3-Azoles:
By:
LinkedIn: Shumookh AlSufyani

Contents:
❑ Introduction
❑ Imidazole and derivative In Nature.
❑ Aromatic characters
❑ Attack of Electrophilic Substitution & Resonating structure.
❑ Electrophilic substitution Reaction Of Imidazole
❑ Application Of Imidazole.
❑ References.

Introduction:
1,3-Azoles are a five-membered heterocyclic
compounds with two heteroatoms, which one is
(N have SP2-Hybridized) with extra hetero
atom ( NH- / O / S ) . There are derive from
Pyrrole, Furan & Thiophene.

Imidazole and derivative In Natural:

Aromatic Characters:
• They are cyclic & planar, Follow Hückel rule (4n + 2 = 𝜋) and
contain a conjugated system of 𝜋 electrons.
• 𝜋−Properties of (pyridine−type N= , SP2) & (heterocyclic with one
atom−Type X− , SP3)

Attack of Electrophilic Substitution
& Resonating structure:

Attack of Electrophilic Substitution
& Resonating structure:
Electrophilic occur in potion have:
• More resonating structure
• High electron density
• More stable N

Electrophilic substitution Reaction Of Imidazole
Halogenation :

Electrophilic substitution Reaction Of Imidazole
Nitration :

Electrophilic substitution Reaction Of Imidazole
Sulphuration :

Electrophilic substitution Reaction Of Imidazole
Acylation :

Electrophilic substitution Reaction Of Imidazole
Oxidation :

Electrophilic substitution Reaction Of Imidazole
ROH Addition :

Application Of Imidazole

Application Of Imidazole

• Fouda,A.(2022). Chapter 4 - Heterocyclic Chemistry,1𝑠𝑡
𝑡𝑒𝑟𝑚, Chem6100 . KSA . KKU
• Gupta, V. K. (2014). Bioactive Phytochemicals : Perspectives for Modern Medicine. Daya Publishing House.
• Vishnu Ji Ram, Arun Sethi, Mahendra Nath & Ramendra Pratap. ( (
2019 . Chapter 5 - Five-Membered Heterocycles.J. The
Chemistry of Heterocycles Nomenclature and Chemistry of Three-to-Five Membered Heterocycles.( 1st Edition) .US .J,Elsevier
References: