Synthèse de l'Ihamine et dérivés
Synthèse de l'Ihamine et dérivés
Amadineu)
NO NH NH
NH
Fe
a
-HA
NC
NHOCHg
NH--Ha
fe\Het,
C0OH
CH3
NOLtHed Na
Mm4 (0H K
CHg
N
Methylae n) 2
2
CHy-CHy NH
- NH
CHa-NH NH2 NH NH2 AWlimeNH
NaNOHA
+
NOz+HeANa 0-s'c
0-S'C
(acyiatiow) C0t CH tA
CMy NH-CH
cHa-CH AQ
Phaline
A), cHa N 2,46ma
I,3SiAmaene
N NH-c0
-CHg Dniline
NN' N'
ined HN0a
Co + -cOCHNH
a-H CH-CtHN S04,
Cone. H NaNO+HO 2
0-s'C
- ihamine
-CH
N
cHoH C0CHg NH
A Ha0(H
cH3A H,0H
Heoth
cH,-
N02
CH,ch
CHW
daeAeMe
AmiiniM)
tAmamem Amine n)ClaehmM )
NH2
NH NH NH2 NH
Awine te
Na
NaNO,
HA + HA
NO
Na HA
NO
No 0-SC Na
diaratization No
0-sC 0-sC NOL L
0.5'C
t HA,
HÞ
Na' BDC
fucNIKCN tutNtkN HO
F4 PUzHg
CH,-NH
H-OH
IV)
PheMeAOH Btynene)iD0- (CH,-CHg
OH
hemeh-kiemah) do
dwtZn-
0NA 2,
Aaliealaeye 4.
4-m
4091% 6
d4MAAhema
Wietote)
whe ( (CHg-CH
OH ,CHO
c.00NO OH
AAn
cOOH
1)
NHa
NH, NHg
Asenzydhhohe
Jolusme A
(DE Na 300 t
-H
CA
hy
NO
Co0H
NH NH,
TetHe
NnQH,
KOHtAa
NH
OHTCaD Na
cH.4-Co
4)
Bmeme H
H
H
H)S10
t gFe iwnzaokim)(FC beyatiom)(EC(FCukyatin)
A HK
-Hd -HA
enaehch
S0H
CHs
CHO
C0-CH
HAAJ Na
O
cO-C6 Hs
(O)
0No
-CH 3
H+
Co0tH
Ht
CHgtot
o
5) 4)
9) 8)
BeAe
Ahanc 4-CN
CH,-
(CH) CHa
CHa
TAhamel khAQhGdate 2 CH- CH
CH-CHg
CHa-CH - CHa-COOH
CHa-cH,0 -CH,
NH(
OH aKid -
te -CHa
FCH 0H
id de
wARAhaad AA de amin
cO-NH2
NooH,
mdham
My50, edhanal CoONa
CGe hattintPCHC
Ha)-C-NH,
Hso C CHafco0
H, 03
CH,-CH =
CH,
CHa-CH,-0H CH- 0H CHg-
909 - Na
NH
C
NaoTA
00
=CH H
CH=0 H WHA
-CH2n NOL
Ha Pod CHa
H C
2 CHa-(ctaJa-NH2 OH+
B12 Na Ha
2CHg-
CH=0 Hg-cHi0 c
Ha -NH
2
1)Phrtmeie R-Cp0 R-C/-NH
2 CHa-CH
2-0H
R-CH -R
cH (1)
H-CHy-- H CH4-
COOH
CHa-CH
- -CHgCHy
Na
aridh t
Na 4
to QH Na
-4ftH
NHAtet OtH
ethameisAd
4,,0 + DE
CHa-C
CHg otHa-cH,-C-oHM20H+
CHa-CH2 ’CHa-CHt
-CH,
H2
H -a -CHa
0H
CNHa
CHENa
O-N=Q)HNO2 4
-
CH tomtt
DENa
-
CHa
CHa-cH-cH-CH
H,-CiCHCH,-C
-ct,-c=NCHg
No
HO (NSK'CN
Methaal Ha-CH2C CH-CH 2
2CH-CH
CH-CHo +
+
Gg-CH,
CHa-CHÌ CH,-CH=CH-CH0 BH4Na -cH,-cHçOHaAH4
tatot tatoo-j
dil ct
’
Na Nao4 ’CHg-CH-CH,-CH =0
0H CtHa
,cHa CH tH
-CH
-CH,
-ch-cHO GH-CHCHO -CH-CHH-CH =0 -CH-
CHa
-H,0
-CH
cH =
-CHO
=CHCH, kinmomaledehyde
hajaa)
Phey 3 H
0 =0
TH=CH-CHO 6HyNa
|Cowe
SIaH, CH-CH Hso4
-H0
H2S04
0
2-CH C}
- 2CHy-
H
C
DE
i. KCN W)
Naot t. Na to
OH,
CH,-CH AremeaAd
)0=C=0
O14
-cH=0
-CH, H-CH,-CHEO H
CH=0
cH-CHg
-He0
S13K
tt
tae
2CHy-
ChAetlhaMeV)
CHa-CH2 CH,-C-U
H; CH,-C
CH, CH,-CH,-c
hlethane
CH¡-CH, ta
-
H,- CH,
OH d - -
CH A
- CN
K*
Rd K*CN
H twSR)CH,
CH,-cEN -KU
-KU
tNSR(H4-c-CEN H, K*CN
CH,-CH,-CEN
’
’CHaCH,-C N
UH
e
CHa-CH,
-CSN
N HNO 2
g-CH2-c=
=0) N
CN
CHa CH,
H,-cH;-C C (tehemhid'
H0
tH A[H}
NCtlg
-H, CH -CH, -
CtH,-C=O
CH- -C C
H,
H, -CH
-c -CH,
=0 (HO=0)HNO2
-N
CHg
NH, -0H
CHa-CO
(me!
(aleeho)
O=C= O
CHa-CH- GH4-OH
CH¡- OM)
-H2
CH3-CH CHy-CH-CH
CHa-C Ha ü) H,0Ht
S13K
-Ha
2
OH
4) Aezaloehycde e aetahemse
CH
tu
S73
’ CHn-C- CH,
) H0 |H
CHa
KMM O4 IH
’CHa -C00H + i
#cH2
-c00H)
KmwosH, 2c H a
cH-CHa
cHaBo0o
’CHac00H
/0H*
K MM O 4
to ethameC a
10) BankaMe-2gl
C C H 2 - cHa
cH,-
OH
2|CHa- Co0H
ct
6 HO0 C-(CHz-co0H
12) aeme
CH-CH3
Km0 |0H
¿-cH3
1s)ene
AtanzaldslaydCHO
KMO4 10Ht
V) h0le|CS
1X) 2 A 4 s OH
CHa -CH-CH =0
CH=O
4) Bakam-2-Al
CHa-H-cH,- cH
s) B u t a m - - e
-cH,- COOH
Ha-CH,-CHa-0f) KMmo4 10H ’ CH- CH,
CHa-C
coOH
CHa- OH KMyO4 TOH
cH, H)
443K
-H20
Mydoatom
cHa -CH -CHg
cHa -CHa-CHa 4 43 K
-Ha0
s0tyH CH=H
;dahydhakian)
CH- CH2-CH0H
KOttt,
ttt Nai
CHa-H=CH,
CHgC2-CH
+H A
CH 4-CH = CH,
Redutinag agt
H|Pt
U)D16AL- H
|HA
N) H2N -NH, lOH
x) felHA
mHA
CH= 0 CH2-H
H4 tPt
2(H)
4 (H) Ha tc Ha-0H
-2Ha0
Co0H
4(H]
- 2 He0
-CHa
CHa-CH
-CHo-OH CHa-CH=CH
CH-CHAh.
Prhog +HA
CH-cHa-
CHe
)J(henie
CHa
-CH=CHa
CHa-
CH-CHa CH2
Hg
- OH LoHn3
-CH
CHa
Hg
ydsalia B20,
H1
4 H,
+HA )
H=CH, 2
CH2
CH-CH= H2-CH CH
-CH
-CH=CHa
CHg C
Ho-CH=CHa
CHg-C
-C
CH CH
rthanawe twwy
CHo-Ct2-NH,
RAhaMimithie ta
6) CHa-N 4 (HJ
NH,
Ai AA H4 ’ctla- ctg -
-HO
CHa -c - NH
CHo-C=N
(ateihenhed")
Aenazaldcayce
CHO
DIGAL-H
CHO
PdeaSO41s
CH-CH,- CH=0
14)
Phaagan NH-N Ha0H"
9CHa-CH-cHa
CH-0 NtHe-NHL) 0H°gyeel