Organic Chemistry of Drug Synthesis. Volume 7

N

N N

N

Cl

Cl

N

N N

N

Cl

Cl

C 6 H 5 CO (^2) O
O
O
O
O
O
HO
95
CH 3 C 6 H 4 SO 3 Cl O
O
O
O
O
TsO
96
KF O
O
O
O
O
F

1. H 2 SO 4


2. C 6 H 5 COCl

O

OH

OH

HO

C 6 H 5 CO 2

F

CH=OCH=O KIO^4

O

HO

C 6 H 5 CO 2

F

97

99 98

C 6 H 5 CO (^2) O
HO F
OH

1. Ac 2 O


2. HBr

C 6 H 5 CO (^2) O
HO F
Br
100
101
102 SI(CH^3 )^3
HO F
NH 3
N
N N
N
NH 2
Cl
HO O
HO F
103 104
Nerve cells are known to elaborate proteins that guide early development
of the nervous system and in later life play a role in cell repair and regen-
eration. A purine that crosses the blood–brain barrier has shown activity
similar to those endogenous factorsin vitroas inin vivomodels of nerve
damage. Conjugate addition of adenine to ethyl acrylate in the presence
of base leads to the ester ( 106 ). Reaction of that product with sodium
N
N
NH
N
NH 2
105 CO 2 C 2 H 5
CO 2 C 2 H 5
N
N
N
N
NH 2
106

1. NaNO 2

CO 2 H

N

HN

N

N

O

107

2. NaOH

O

NO 2

F 3 C

O

108

N

HN

N

N

O

O

O

NO 2

109

CO 2 H

CO 2 C 2 H 5

H 2 N

110

2. NaOH

N

HN

N

N

O

O

NH

111

1. COMPOUNDS WITH FIVE-MEMBERED RINGS FUSED TO SIX-MEMBERED RINGS 201