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Ammoniaque
NH4
NH2
+H pKa = 9.4
-H+
Pyrrolidine
H
N H
Pyrrole
H H N H
Pipridine
-H+ N +H+ pKa = 11.1 N H
Pyridine
-H+ N H +H+ pKa = 5.2 N
170
+ RCH2 N CH2R
Br
O RC Cl N H Pyrrolidine O N R
171
Ph N N X
Pyrrole
N H N H
N N
Ph
Position 2 vs position 3
Position 2 E + N H Position 3 N H E+ N H H E H N H N H E H E H N H E H
+ N H
H N H H
N H N H
H N H
H H
172
N Pyridine
Benzne
S Thiophne
O Furane
AlCl3
>
>
>
>
N H Pyrrole
NaH
174
H2
Raction d'addition-limination
2-Aminopyridine
175
N R
OH / H2O N CH3
NaBH4 N CH3
O O O OEt NH2
O OEt
Me
CO2Et
CH3CO2H
EtO2C
N H
Me
O NH3 Cl +
Me NaOH N H Me
Problem E5
177
O + OEt NH3
O OEt + H
O H
178
H EtO2C Me N H
179
HO OH
OH
180
j) Alcalodes
Bases azotes qui ragissent avec des acides pour donner des sels solubles Ce sont des amines qui prsentent des effets physiologiques remarquables
O H N N Me N OH
Problme F1
Me H N
Me N CO2Me H H O O Ph
O O
H Ph CH2OH
Problmes F2-F5
181
j) Alcalodes de lopium
HO HO
NH3 CO2
HO HO Dopamine
NH2 + HO HO O CO2
2-(3', 4'-dihydroxyphnyl)thylamine
OH OH
182
j) Alcalodes de lopium
HO HO HO2C N H
HO HO N
MeO MeO N
Papaverine
OH OH OH OH OMe
OMe
MeO HO HO MeO C C N
MeO HO O MeO C C N
MeO HO C C MeO O
183
Me
j) Alcalodes de lopium
MeO HO C C MeO O N Me
MeO C C H HO N Me
AcO C C H AcO
HO C C H HO N Me
O N Me
Problmes F6-F9
184