Pyridines,Quinolines and

Isoquinolines
TYPICAL REACTIVITY, REACTIONS AND SYNTHESIS
QUINOLINES AND ISOQUINOLINES
Synthesis of Pyridines
From 1,5 - Dicarbonyl Compounds and Ammonia
From an Aldehyde, Two Equivalents of a
1,3 - Dicarbonyl Compound and Ammonia
The Hantzsch Synthesis
From 1,3 - Dicarbonyl Compounds (or
Synthons) and 3 - Amino - Enones or - Nitriles
The Bohlmann – Rahtz reaction
Synthesis From Furans
Examples of Notable Synthesis of
Pyridine Compound -Pyridoxine
Quinolines and
Isoquinolines:Reactions
Substitution at Carbon- Proton Exchange

Nitration- Baake – Katritzky protocol

Sulfonation

Halogenation
Reactions with Nucleophilic Reagents
Nucleophilic Substitution with ‘ Hydride ’ Transfer-
Alkylation and Arylation
Amination and Nitration
Hydroxylation
Reactions with Radicals
Reactions with Reducing Agents
Oxy - Quinolines and Oxy -
Isoquinolines
Amino - Quinolines and Amino -
Isoquinolines
 Synthesis of Quinolines and Isoquinolines
-Ring Syntheses
-Quinolines from Aryl - Amines and 1,3 - Dicarbonyl Compounds

The Combes Synthesis

Conrad – Limpach – Knorr
Reaction
Quinolines from Aryl - Amines and a , b - Unsaturated
Carbonyl Compounds

The Skraup Synthesis

Quinolines from ortho - Acyl - Arylamines and Carbonyl
Compounds

The Friedländer Synthesis

The Pfitzinger Synthesis
Other Methods for Quinolines
Isoquinolines from Aryl - aldehydes and Aminoacetal

The Pomeranz – Fritsch Synthesis

Isoquinolines from 2 - Aryl - Ethanamides or 2 - Aryl -
Ethamine - Imines
The Bischler – Napieralski Synthesis
The Pictet – Gams Modification
Isoquinolines from Activated 2 - Aryl - Ethanamines and
Aldehydes (The Pictet – Spengler synthesis)
Examples of Notable Syntheses of Quinoline and Isoquinoline
Compounds
Chloroquine
Papaverine
THANKS