AZINE

N
N
N
Piridazina

N
Pirimidina

N
Pirazina

Piridazina (1,2-diazina)
Obtinere
O

O
O +

NH
NH

NH2
NH2 - H2O

OH

Cl

N POCl3
N
OH
Piridazindiol

N H2
N Pd / C
Cl

N
N
Piridazina

O
O +

NH2

N
N

NH
NH

NH2 - H2O

OH

OH

ftalhidrazida

OH

O
NH
NH
O

+
N
N Sint.Dien

N [O]
N
OH

O
1,4-Ftalazindiona

[O] -= hipoclorit de tert-butil, tetraacetat de Pb

N
N
O

Pirimidina (1,3-diazina)
Obtinere
NH2
O C

OH

O
ROOC
+

NH2
Uree

CH2
ROOC

EtO
- 2 ROH

NH

Ester malonic

HO

HO

Cl
POCl3

Acid barbituric

OH
N

taut.

HN

OH

Zn, H2O

N
Cl

Cl

N
N
Pirimidina

OH

Derivai ai pirimidinei
Uracil (2,4-dihidroxi-pirimidina)
OH
NH2

ROOC
+

O C
NH2
Uree

EtO

CH2
OHC

HO

Ester formilacetic

+ ROH + H2O

N
Uracil

Citosina (2-hidroxi-4-amino-pirimidina)

NH ROOC
C2H5S C

NH2
Etil-tiouree

CH2

EtO
-ROH
-H2O

OHC
Ester
formilacetic

C2H5S

OH
N

POCl3

NH2

Cl

C2H5S

NH3

C2H5S

NH2
H2O

HCl

N
HO
Citosina

2-Amino-pirimidina
OH
NH ROOC
+
CH2
H2N C
OHC
NH2

EtO
-ROH
- H2O

POCl3

N
N

H2N

Cl
red.

H2N

H2N
N
2-Amino-pirimidina

Reactivitate

N
N

N
N

N
N

N
N

N
N

Caracter aromatic derivaii substituii la nucleu cu grupe aril, halogen, alchil i nitro
- scade pe msur ce se introduc la nucleu grupe OH i -NH2
- substituia electrofil decurge greu

O
NH2
O C

ROOC
+

NH2

Et
C

ROOC

NH

EtO

O
Et

Et

Et
NH
Veronal O

+ 2 ROH

Pirazina (1,4-diazina)

N
N
..

N
..

N
..

N
..

..
N
..

..
N
..

N
..

N
..

Obtinere
H2N

R C=O
R CH

+
NH2

CH R
O=C R

R
R

R
R

2,3,5,6-tetraalchilpirazine

N
2,5-dimetilpirazina

N
2,3,5,6-tetrametilpirazina

nuci prjite

cafea prjit

2-acetil-3-etilpirazina

N
2-metil-3-etilpirazina
nuci prjite

COCH 3

cartofi copti

NH

COCH 3

2-acetil-1,4,5,6-tetrahidropiridina

COCH 3

N
2-acetilpirazina
popcorn

COCH 3
2-acetilpirol

6
1

PURINE

N
8

N
3

N9
H

Obinere
Sinteza Baeyer-Fischer

NO

HN

HN

HNO2

O
NH
O
Acid barbituric

4[H]

NH

HO

OH

N
H
Acid uric
N

NH2

HN
O

OH
-H2O

HNCO

NH
Uramil
Cl

Cl

POCl3

Cl
N

N
H

NH

HN

red.

NH

CO
NH2

N
N
Purina

N
H

Sinteza Traube
OH

OH

NH2 ROOC
NO
NH
H EtO
HNO2
N
H
N
+
C
O
O C
H - ROH
NC
H
NH2
NH
N
NH2
NH2 HO
HO
N
NH
Uree
Ester cianacetic
6-Aminouracil
OH
OH
OH
NH2
red.
- ROH
N
NH
N
Cl-COOR
N
N
OH
COOR
N
HO
N
NH2
HO
N
NH2
HO
N
5,6-Diaminouracil
Acid uric H

O
NH2 ROOC
H
C
S C
+
H
NC
NH2

NH

EtO
-ROH

Tiouree
OH
N
HS

OH

NO
red.

NH2

HS

NH2

HNO2

H
N
HS
NH
6-Aminotiouracil

NH2
OH

OH

NH2
HCOOH

S
NH

OH

N
HS

N
H

HNO3

N
H
Hipoxantina
N

HN C

NH2 ROOC

H EtO
C
H -ROH
NC

NH2
Guanidina

NH
HN

H
H
NH

NH

NH2

2. red.

H2N

N
H2N

HCOOH

H2N

NH2

N
H

N
Guanina

S C

NC

NH2
NH2

Tiouree

H
H

NH
NH
H
S
H
NH
NH

EtO

NC
Dinitrilmalonic
NH2

HCOOH

N
HS

NH2

HS

NH2
NH2

2. red.

HS

NH2

NH2

NH2
1. HNO2

OH

OH
1. HNO2

OH

N
H

HNO3

N
N

Adenina H

NH2

OH

Cl
N

POCl3

OH

HO

Cl

Cl

3HI

H
EtO-Na+

NH3
KOH

NH2
N

N
Cl

2. HI

N
H

N
N

H
Adenina

OH

NH2

Cl

H2N

Cl

EtO

N
HI

OH

N
H

Guanina

N
N

N
H

OH
N

Cl

HI

HI

1. NH3

Cl
N

OEt

OH

N
HO

H
Hipoxantina

Xantina

NH2
O

HO P O P O P O CH2
OH

OH

OH
ATP

OH

OH

HO

NH2

OH
N
OH

CH2 O P O P O CH2
O

CONH2

O
O

O
OH

Codehidraza I (DNP)

OH

cafeina

teobromina

teofilina