Ntheaia & Bepornbion: Pypimicline

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ntheaia & Bepornbion

Pypimicline
uimidaine us a n aiomaie heteoce
olganic cowpun Sumilas fe pyuidne
One o e thue cluazinesthas a
itlesen atms at postens 1&3 in

un e Caben arel hdtngem cueCBnhectrd


via allenating dpure anel Airgle eols
Th
Ag system is phnt n many
natiua pioduks ike huceic auol Cune
Suntibe dungs ike balbituuate

Pyiwmione
Supthesis
meuy be pAepaied o
()Ryumidine
le Corclonsatíon e
boitutic acid ounf by
malee esteu Gnel ula.

CoOH CHONVa
H,C + HN
CoOC,Hs H,N C4OH

H OH
O
N
Taut s
HC
C-N
C =0
LCH C=N
c-OH

H OH

C
POC >
o HI N

ficine
Comdensatien 3-dicabon Cempeud uith
weA in pALne 2HONa givs boubitiuuic ced
i
whic o etd -ehe tutomewm
is
pyinidne 24,6--tn'ol huther it on tuatmt
with Pougleue by tuatnet with zinc dust
gi PyAmidine
() dkom amdine
O HN
p MeonaMoH
-R
+
e
N

(ii) m 24-cichleiepynidune
C

H2-PalC
-2HU
24 Pyumone

amoune
24-dichloiepyumucdure

em Pyumiolunes

CI CooH
deobunyehen
co)
Co 2
imudune -4-cakoye idise
4-mtpyuimdune acid
Recaon o imduno.
a) (Reacteons ith audl ( Pastor athon)
a)
ves P i d u r i u n salks

H
C

H
imdine u n d m u m clotirle

bQuotesnizaen /N-alkylatn

N CH
TO
A

fyvudine CHa
et puimioli naie
iedide.
C)lthopk.ie asendie ustituton
Renctons Ri'mdhe

Less
ess active due u r itiogen
pAesent in He skeletonPcte poible
ot stiongy electuon
an Case o PAesenCe
te ig
3oup (-wu2)-oH)
on
clevt
Subsbtuben aku place at s positon.
HNO3 H2504
Nitrab
oN
6 NH2

Has0 olwg
Sulphendin

NH2
s t a elton
doci B-2CH&eoH
3

Halogeaba,
d) Oxidatven

N
alkune kMn
CoOH

Nudeopiie subrtithon Reactior

imidine uncdegecs hudesphli


Subtuten eactens at 2he peatem
NanH2

icy NH
NH2

KOH
6 OH
5r

s
With oxiclizin agents

mcPBA

N CHCa
CI

m-Chletepeioaybenzeic aud

O
O OH

Ca with uduci agens CoBn

Na3CCNDE
CIco,B n, Me ODH -
co,Bn
Benzyfhletsiate
Socuuw
jansbomohydnd

O Nat

N BH

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