1. AAZZIINNEE
N
N
N
N
N
N
Piridazina Pirimidina Pirazina
Piridazina (1,2-diazina)
OObbttiinneerree
POCl3
N
N
Cl
Cl
N
H2
Pd / C N
Piridazina
O
O
O
NH
O
NH2
NH2 - H2O NH
O
OH
N
N
OH
+
Piridazindiol

2. O
O
O
NH2
NH
NH2 - H2O NH
O
O
OH
N
N
OH
+
NH
NH
O
O
OH
N
N
OH
N
N
O
O
N
N
O
O
+
Sint.Dien
[O]
1,4-Ftalazindiona
ftalhidrazida
[O] = hipoclorit de tert-butil, tetraacetat de Pb

3. Pirimidina (1,3-diazina)
O C
NH2
NH2
ROOC
CH2
ROOC
EtO
- 2 ROH
O
HN
O NH
O
N
OH
HO N OH
+
Uree Ester malonic
Acid barbituric
taut.
OObbttiinneerree
N
OH
POCl3 N
HO N OH
Cl
Cl N Cl
Zn, H2O N
N
Pirimidina

4. Derivaţi ai pirimidinei
Uracil (2,4-dihidroxi-pirimidina)
ROOC
O C EtO
CH2
OHC
NH2
NH2
N
OH
HO N
+ ROH + H2O
Uracil
+
Uree Ester formilacetic
Citosina (2-hidroxi-4-amino-pirimidina)
POCl3 N
Cl
C N 2H5S
NH3 N
NH2
C N 2H5S
H2O
HCl
NH2
N
N
HO
ROOC
CH2
OHC
EtO
N
N
C2H5S
OH
-ROH
+
Etil-tiouree Ester
formilacetic
C
NH
NH2
C2H5S -H2O
Citosina

5. 2-Amino-pirimidina
ROOC
CH2
OHC
EtO N
OH
H2N N
-ROH
- H2O
C
NH
NH2
H2N + POCl3 N
Cl
H2N N
N
red.
H2N N
2-Amino-pirimidina
N
N N
N N
N
N
N N
N
Reactivitate
Caracter aromatic – derivaţii substituiţi la nucleu cu grupe aril, halogen, alchil şi nitro
- scade pe măsură ce se introduc la nucleu grupe –OH şi -NH2
- substituţia electrofilă decurge greu

6. ROOC
+ + 2 ROH
C
ROOC
Et
Et
EtO
C
NH2
O
NH2
NH
NH
O
O
Et
Et
O
Veronal

7. Pirazina (1,4-
diazina)
N
N
N
.. .. N
N
N
N
N
N
.. ..
.. .. ..
N
.. ..
N
N
..
R C=O
R CH
NH2
H2N
CH R
O=C
N
R R
R N
R
N
R R
R N
R
R
+
2,3,5,6-tetra-alchilpirazine
OObbttiinneerree

8. N
N
N
N
N
N
N
N
2,5-dimetilpirazina 2,3,5,6-tetrametilpirazina 2-metil-3-etilpirazina 2-acetilpirazina
nuci prăjite
N
N
nuci prăjite cafea prăjită
NH
COCH3
COCH3
popcorn
COCH3 N COCH3
2-acetil-3-etilpirazina 2-acetil-1,4,5,6-tetrahidropiridina 2-acetilpirol
cartofi copti

9. PPUU
RRIINNEE
6 7
N
5
N
N N
H
1
2
3
4
8
9

10. Obţinere
Sinteza Baeyer-Fischer
HN
O
O NH
O
HNO2 HN
O
O O
NH
NO
4[H] HN
O
O O
NH
NH2
HNCO HN
O
O NH
O
NH
CO
NH2
Acid barbituric Uramil
-H2O N
N
N
N
OH
H
HO
OH
Acid uric
POCl3 N
N
N
N
Cl
H
Cl
Cl
red. N
N
N
N
Purina H

11. Sinteza Traube
ROOC
C
NC
H
H
O
EtO
H
- ROH
H C
NH2
O
NH2
N
OH
NH NH2
HO N
NH
O
NH
6-Aminouracil
+
Uree Ester cianacetic
HNO2 N
OH
HO N
NO
NH2
red. N
OH
HO N
NH2
NH2
5,6-Diaminouracil
OH
NH
N - ROH
HO N
COOR
NH2
Cl-COOR
N
N
Acid uric
N
N
OH
H
HO
OH
ROOC
C
NC
H
H
EtO
C
NH2
S
NH2
N
OH
HS N
NH2
NH
-ROH H
NH
S
O
H
NH
6-Aminotiouracil
+
Tiouree
HNO2
N
OH
HS N
NO
NH2
OH
red. N
HS N
NH2
NH2
OH
N
N
N
NH
Hipoxantina
HCOOH N HNO3
N
N
NH
HS
OH

12. ROOC
C
EtO C
NH2
NC
H
H
HN
O
H
H
NH2 N
OH
H2N N
NH2
NH
NH
NH
HN -ROH
N
N
N
N
H
NH2 HCOOH
H2N
OH
1. HNO2
2. red. N
OH
H2N N
NH2
Guanina
Guanidina
NC
C
NC
HH
C EtO
NH2
S
NH
H
H
NH2 N
NH2
NH
HS N
NH2 NH
S
NH
1. HNO2
2. red.
N
NH2
HS N
NH2 HCOOH N
NH2
N
N
N
H
HS
NH2
HNO3 N
N
N
N
H
NH2
Tiouree Dinitrilmalonic
Adenina

13. N
N
N
N
H
HO
OH
OH
POCl3 3HI N
N
N
N
N
H
Cl
Cl
Cl
N
N
N
H
EtO-Na+
KOH
NH3
N
N
N
N
H
OEt
EtO
Cl
N
N
N
N
H
OH
HO
HI
N
N
N
N
H
OH
Cl
Cl
HI
N
N
N
N
H
OH
1. NH3
2. HI
N
N
N
N
H
OH
H2N
N
N
N
N
H
Cl
NH2
Cl
HI
N
N
N
N
H
NH2
Adenina Guanina Hipoxantina Xantina

14. NH2
N
N
N N
HO O CH2
OH OH
O P
ATP
O
O
O P
P
OH
O
OH
O
OH
HO OH
N
O
CONH2
O
O CH2 O
OH OH
OH
CH2 O P
O
O P
O
Codehidraza I (DNP)
N
N
NH2
N
N

15. cafeina teobromina
teofilina