Page 62 - Org 3 theoritical book 2024-25

Clinical Pharmacy PharmD - 2024/2025 Level 2 Pharmaceutical Organic Chemistry-3 (PC 305)
B- Benzo-Fused Ring Systems of Pyridine Nucleus

1- Quinolines and Isoquiniolines

5 4 5 4
6 3
6 3
7 N 2 7 N 2
8 1 8 1

Quinoline Isoquinoline

1-benzopyridine 2-benzopyridine

Synthesis of quinolines and isoquinolines:

I- Quinolines

1) From arylamines and ,-unsaturated carbonyl compounds:

Anilines react with an ,-unsaturated carbonyl compound in the presence of an

oxidizing agent to give quinolines.

O 1) - H2O
R R
NH 2 2) - H 2 N

A- Skraup synthesis :

H SO 4
2
HOCH -CHOH-CH OH CH =CH-CHO
2
2
2
2
glycerol - H O acrolein
O OH
H H 1,4- H cyclization
N: addition N - H O
2
H
H

oxidation
N - 2H N
H

1,2-dihydroquinoline quinolone