Chapter 6 Quinolines and isoquinolines: Reactions and synthesis Pyridine N Quinoline N Isoquinoline N Quinolines and isoquinolines: Benzo condensed pyridines N Quinoline Benzo[b]pyridine (1-azanaphtalene) a b c 1 2 3 4 4a 5 6 7 8 8a N Isoquinoline Benzo[c]pyridine (2-azanaphtalene) a b c 1 2 3 4 4a 5 6 7 8 8a
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Quinolines and isoquinolines : Benzo condensed pyridines · Exchange of halogen etc. N X NX N X X=halogen Reactivity towards Nu as NX N X. ... kap6.ppt Author: Lise-Lotte Gundersen
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Chapter 6
Quinolines and isoquinolines:
Reactions and synthesis
Pyridine
N
Quinoline
N
Isoquinoline
N
Quinolines and isoquinolines:
Benzo condensed pyridines
N
QuinolineBenzo[b]pyridine(1-azanaphtalene)
abc
1
2
3
4
4a
56
7
8
8a
N
IsoquinolineBenzo[c]pyridine(2-azanaphtalene)
abc
12
3
4
4a
56
7
8
8a
Quinoline
N
Isoquinoline
N
Quinoliziniumcations
N
chapt. 25
N NN
pKa 5.2 pKa 4.9 pKa 5.5
Reaction with electrophiles
Protonation on N
Electrophilic Ar subst
N
E
N
N
E
N
Major isomers shown
E
E
Benzene more electron rich
than pyridine
Halogenation in the pyridine ring
N
HCl
Br2
NH
N
H Br
H
Br Br
N
H Br
H Br
H
- H
Br
N
Br
H
H Br
N
Br
- HBr
N
HCl
Br2
N
Br
Reaction with nucleophiles
N
Nu
N Nu
N
Nu
N
Nu
N
Nu
N
Nu
c.f. react ! to N in pyridines
Exchange of H
Exchange of halogen etc.
N
X
N X N
X
X=halogen
Reactivity towards Nu as
N NX
X
ANRORC (Add. of Nu., Ring Opening and Ring Closure)