D VNG 6 CNH 1 D T PIRIIN

N ..

PYRIDIN

I. IU CH
1. T ,-anehit cha no
CH3 2CH2=CH-CHO + NH3 - 2H 2O N ..

2. Chng ct hc n than
HC HC HC N CH CH N
2

PYRIDIN
I. IU CH

3. Tng hp Hantzsch
R C EtOOC C R' O H N H EtOOC R' R R N H O O C R'' COOEt EtOOC R' R H COOEt R'' H

- 3H2O

N H

- 2[H]
R COOEt R''

R' N R''

HOOC R' N

COOH R''

+ H2O - 2EtOH
3

- 2CO2

PYRIDIN

II. HA TNH
Hirocarbon thm + tnh baz
+ +

N ..

N ..

+

N ..

N ..

+
4

PYRIDIN
II. HA TNH

1. TH ELECTROPHIN : Piriin < Benzen v N ht eRX RCOX / AlCl3

KNO3 / H2SO4

N ..

Br2 SO3 / H2SO4

NO2 N .. N ..

Br N ..
5

SO3H

PYRIDIN
II. HA TNH

2. TH NUCLEOPHIN

C4H9Li

N ..

KOH

NaNH2
N .. C4H9

- NaH
NH2
+

N ..

OH

N ..

NH2

N ..

-aminopiriin

-aminopiriin

PYRIDIN
II. HA TNH

3. CNG (hiro ha = kh)

H2 Pt

.. N H

Na

Na

Na

N ..

EtOH

.. N H

EtOH

.. N H

EtOH

.. N H Piperidin

LiAlH4

.. N H 1,2-dihydropyridin
7

PYRIDIN
II. HA TNH

4. OXY HA
Bn vi Br2, KMnO4 long Tc dng vi H2O2

NO2

NO2

H2 O2
N N O
N-Oxit

HNO3
N O

[H]
N

dn xut th p ca pyridin

PYRIDIN
II. HA TNH

4. OXY HA Oxy ha gc hirocarbon

[O]
N

CH3
N

COOH

-picolin -picolin picolin

axit picolic axit nicotinic axit isonicotinic

PYRIDIN
II. HA TNH

5. TNH BAZ : baz yu # amin bc 3

HCl

CH3I

N H

Cl

N ICH3

Piriin hirochlorua

N-metylpiriin ioua
10

PYRIDIN PYRIDIN

NG DNG

H3COOC H3C N

NO2 COOCH3

CO NH NH2

CONH2
N

CH3

Nifeipin = Aalate

Isoniazit = Rimifon

Nicotinamit = vit PP

CH2OH HOCH2 N OH CH3 HOCH2

CHO OH N CH3

Pirioxol

Pirioxal = vit B6

11

PYRAN
O O

-Piran (4H)

-Piran (2H)

Khng c tnh thm

12

D VNG 6 CNH 1 D T QUINOLIN

5 6 7 8 4 3 2 1 6 7 8 1 5 4 3

N2

Benzo[b]piriin quinolin

Benzo[c]piriin isoquinolin
13

QUINOLIN

I. IU CH
1. Tng hp Skraup
CH 2OH CHOH NH 2 CH 2OH C 6H 5NO2
++

Fe /H2SO4 N + C6H 5NH 2 + H2O

2. Tng hp Friedlander
O CHO NH .. 2 CH 3 CHO - H 2O C H N CH3 - H 2O N
14

CH

QUINOLIN

II. HA TNH
1. TNH BAZ : yu hn Piriin

CH3I
+

CH3

15

QUINOLIN
II. HA TNH

2. TH ELECTROPHIN : kh
HNO3/H2SO4
8

NO2 N SO3/H2SO4
8

N SO3H
CH=CH C O X

FORMYL HO
1) CHCl3, KOH, 80oC N OH 2) CH3CO X HCl

N OH
16

QUINOLIN
II. HA TNH

3. TH NUCLEOPHIN

NaNH2
2

NH2

17

QUINOLIN
II. HA TNH

4. CNG
N [H] Na / EtOH
Tetrahiroquinolin

H N

[H] Na / EtOH

H N

Decahiroquinolin

5. OXY HA
N KMnO4 HOOC HOOC
18 Axit quinolic

III. CC DN XUT QUINOLIN

Quinolon th h 1 v 2 : khng khun
O COOH H 3C N N CH3 HN F N N O COOH

Axit naliixic = NEGRAM

Ciprofloxacin = CIFLOX

19

III. CC DN XUT QUINOLIN

Dn xut ca quinolin tr st rt
Quinin
CH3O C 2H 5 C O O N

H H N C H H H CH=CH2

20

III. CC DN XUT QUINOLIN

Dn xut ca quinolin tr st rt
NH R
8

Cl

CH3O

NH R

CH3 R = CH (CH2)3 N(C2H5)2

CH3 R = CH (CH2)3 N(C2H5)2

Pamaquin = PLASMOCHIN

Chloroquin = NIVAQUINE

21

BENZOPYRAN
OH

Coumarin
OH CH 2 O O O

4-hydroxycoumarin
OH

O
O

icoumarol

O Benzo--piron (vitamin E)

22

D VNG 6 CNH 2 D T
I. NHM IAZIN
N N N N N N

1,2-iazin Piriazin

1,3-iazin Pirimiin

1,4-iazin Pirazin

23

I. NHM DIAZIN

Khung axit barbituric

OH N HO N OH R1 R2 O O NH N H O R1 R2 O O NH N H S

Barbituric : gy ng

Thiobarbituric : gy t, m

24

I. NHM DIAZIN

Cc acid nucleic
Khung Pirimiin
OH N N OH CH3 N OH N OH N NH2 N OH

Uracil Khung Purin

NH2 N N N H N

Thymin

Cytosin

O HN H2N N N H
25

Aenin

Guanin

I. NHM DIAZIN

Khung Purin
OH N HO N N H N OH N N N H OH N

Axit uric

Allopurinol

H3C HOCH2CH2 S

Cl + N

NH2 N N CH3

Thiamin (vitamin B1)

26

D VNG 6 CNH 2 D T
II. NHM THIAZIN
8 7 6 5

R N
10 1 2 3 4

S
9

Phenothiazin
N
+

(CH3)2N

S Br

N(CH3)2

Xanh methylen St trng, tr gh, tr ng c c dn Lm phm mu, phm nhum cng nghip
27

II. NHM THIAZIN

8

R N
10 1 2 3 4

Phenothiazin

7 6 5

S
9

DCI Promethazine Chlorpromazine Alimemazine Fenoverine Diethazine

Hot tnh Khng histamin H1 An thn

X H H, Cl, CN, CF3

R
CH3 CH2 CH N(CH3)2

CH2

CH 2

CH2 N(CH 3)2

O O

Gy lit c Tr Parkinson

H H

C CH2

N CH2

CH2

CH2 N(C2H5)2
28