C

N
N
C
C
C
C
N
C
C
C
N
C
N
C
C
C
N
I)
II)
III)
Grupa pirimidinei
Metode de preparare
H
H
S=C
NH
2
NH
2
CO
2
C
2
H
5
CH
2
CO
CH
3
C
C
C
N
N
OH
CH
3
HS
N
N
C
C
C
OH
CH
3
HO
4-metil-uracil
NH
H
2
N C
NH
2
OCOC
2
H
5
CH
2
OCOC
2
H
5
N
C
N
C
CH
H
2
N OH
OH
+ 2ROH
2-amino-4,6-dihidroxi-
-pirimidina
tiouree ester acetil-acetic
guanidina ester malonic
NH
2
CO
NH
2
ROOC
CH
2
ROOC
-
2ROH
N
N
OH
OH HO
POCl
3
N
N
Cl
Cl
Cl
Zn
N
N
acid barbituric
pirimidina
uree ester malonic
NH
2
CO
NH
2
ROOC
CH
2
OHC
N
N
OH
HO
2,6-dihidroxipirimidina
(uracil)
uree ester formil
acetic
N
N
N
N
N
N
(+)
(-)
N
N
(+)
(-)
I II III IV
N
N
(+)
(-)
N
N
(+)
(-)
N
N
(+)
(-)
V VI VII
Proprietati
N
N N
N
HOOC
HOOC
-
CO
2
1
2
3
N
N
HOOC
N
N
CH
3
NH
2
Na
+
-
N
N
CH
3
+
-
N
N
CH
3
-
H
H
2
N
Na
+
-
NaH
N
N
CH
3
H
2
N
N
N
RO
OR
OR
ROH N
N
Cl
Cl Cl
NH
2
R N
N
NHR
NHR RHN
HI
N
N
HSR
N
N
SR
SR RS
Reactii SN
Reactii SE
N
N
NH
2
N
N
H
NH
I
II
lactam
lactim
IV III
II
I
H
O
O
N
HN
OH
HN
O
N
O
N
HN
HO
OH
N
N
HO
CH
3
H
3
C
O
N
N
CH
2
N
2
O
N
HN
HO
OH
N
N
H
O
O
Hidroxi- si amino-pirimidine
citosina
timina uracil
NH
2
CH
3
H
O
-
N
C
N
CH
CH
O
-
H
O
-
HN
C
N
CH
C
O
-
H
O
-
HN
C
N
CH
CH
Acidul barbituric
II
I
H
O
C
C C
N
HN
CH
2
O
O
H
O
C
C C OH
N
HN CH
O
C
C
HN
C
N
O
O
H
CBr
2
O
Br
2
C
C
HN
C
N
O
O
H
CH
2
O
Ar N=N X
-
+
C
C
HN
C
N
O
O
H
O
CH N=N Ar
HNO
2
C
C
HN
C
N
O
O
H
C=NOH
O
HNO
3
C
C
HN
C
N
O
O
H
O
CH NO
2
C
C
HN
C
N
O
H
CH
2
O
O
R CHO
-
H
2
O
C
C=CHR
C
HN
C
N
O
O
H
O C
C
HN
C
N
O
H
CH CH
2
R
O O
veronal
luminal
R
1
= C
2
H
5

R
1
= R
2
= C
2
H
5

R
2
= C
6
H
5
R
2
R
1
O
C
N
N
O
O
H
H
O
O
H
II
I
acid isodialuric acid dialuric
O
OH
O
O C
C
N
C
HN
CH
O C
CHOH
N
C
HN
C
H
Tetrahidroxi-pirimidine
N
C
HN
C
C O
H
O
O
C O
O C
NH
2
NH
2
+ C O
HOOC
HOOC
N
C
HN
C
C O
H
O
O
C O
+2
[
H
]
N
C
HN
C
C O
H
O
O
C
H
OH
acid dialuric
N
C
HN
C
C O
H
O
O
C O
N
C
HN
C
C
O
H
O
O
C
H
+
HO
N
C
HN
C
O
H
O
O
H
O
N
C
HN
C
C
O
H
O
O
HO
aloxantina
Aloxan si derivati
7H-purina
9H-purina
H N
N
N
N
d
c
b
a
9
8
7
6
5
4
3
2
1
H
N
N
N
N
Grupa purinei
HN
N
N
N
O
O O
H
H H
N
N
N
N
OH
OH
HO
H
H
forma lactamica forma lactimica
HN C
OC
HN
C OH
C
O
OH
NH
CO
NH
CH
3
CO
2
H
-
CO
2
HN CH NH
OC
HN C
OH
NH
CO
HN
OC
HN CO
CHNHCONH
2
HN
N
NH
N
O
O
O
KMnO
4
H H
HNO
3
HN CO
OC
HN C
OH
C
NH
OH
NH
CO
HN
OC
HN
CO
CO
CO
+
H
2
N
CO
H
2
N
alantoina
aloxan uree
NH
3
N
N
N
N
H
Cl Cl
NH
2
KOH
N
N
N
N
H
Cl Cl
OH
NH
3
N
N
N
N
H
Cl
NH
2
H
2
N
N
N
N
N
H
Cl
OEt
EtO
dicloradenina
diclorhipoxantina clorguanina 2,6-dietoxi-8-clorpurina
HI
N
N
N
N
NH
2
H
HI
N
N
N
N
H
OH
HI
N
N
N
N
H
H
2
N
OH
HI
N
N
N
N
OH
H
HO
adenina
hipoxantina
guanina
xantina
EtO Na
+
2,6,8-triclorpurina
H
N
N
N
N
HI
Cl
Cl
Cl
H
N
N
NH
N
POCl
3
H H
O
O
O
HN
N
NH
N
N
N
N
NH
NH
2
HNO
2
N
N
N
NH
OH
N
N
N
NH
OH
H
2
N
HNO
2
N
N
N
NH
OH
HO
adenina hipoxantina
guanina
xantina
H
2
N
CO
H
2
N
+
C
2
H
5
O CO
CH
2
CN
-
C
2
H
5
OH
C
O
HN
CO
H
2
N
CH
2
CN
NaOH HN
N
O
O NH
2
H
HNO
2
-
H
2
O
HN
N
O
NH
2
H
O
NO
+ 4H
-
H
2
O
HN
N
O
NH
2
H
O
NH
2 Cl COOC
2
H
5
-
HCl
4-amino-5-nitrozo-uracil
acid uric
O
O
H
O
HN
N
N
C
N
-
C
2
H
5
OH
OC
2
H
5
CO
NH
O
H
NH
2
O
HN
N
H
H
Acidul uric- sinteza Traube
murexid
aloxantina acid dialuric aloxan
NH
4
(-)
:
(+)
:
..
O O
H
N
NH
O
N
H
O
O
O
HN
N
H
2
O 2 -
NH
3
2
H
O
O
O
N
NH
O
H
H
O
O
O
HN
N
HO
H
H
O
O
O
N
NH
+
H
O
O
O
O
HN
N
HO
N
N
N
O
O
NH
CH
3
H
3
C 1
3
7
HN
N
N
N
O
O
CH
3
CH
3
N
N
N
N
O
O
CH
3
CH
3
H
3
C
teofilina teobromina
cafeina
hipoxantina
xantina
O
HN
N
N
N
H
O
O
HN
N
N
N
H H
adenina
guanina
NH
2
H
N
N
N
N
H
2
N
O
HN
N
N
N
H
Xantina, hipoxantina si derivati