Biomedical Engineering Reference
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H
N
N
O
CO
2
R
O
R
3
R
4
C
6
H
4
B(OH)
2
Pd(dppf)Cl
2
,
K
2
CO
3
μ
O
R
1
R
3
O
HN
c
-C
6
H
11
R
1
R
3
O
HN
c
-C
6
H
11
R
1
N
c
-C
6
H
11
N
H
N
N
W 150
o
C, 20 mi
n
AcCl, MeO
H
F-SPE
53-96%
BocHN
O
O
O
F-SPE
15-49%
R
2
30
31
32
OSO
2
C
8
F
17
R
2
R
2
C
8
F
17
O
2
SO
R
4
H
2
N
CO
2
R
29
MeOH
R
3
F-SPE
52-99%
NC
R
2
NHBoc
R
1
C
8
F
17
O
2
SO
CHO
OH
25
O
MeOH
R
4-
NC
R
4
F-SPE
R
5
-NH
2
52-99%
R
2
R
2
OSO
2
C
8
F
17
R
4
C
6
H
4
B(OH)
2
Pd(dppf)Cl
2
,
K
2
CO
3
μ
R
5
O
O
R
1
O
R
4
N
TFA-MeOH
H
W 150°C, 20 min
F-SPE
20-69%
HN
HN
R
5
R
5
N
N
BocHN
O
μ
W 150°C, 20 min
F-SPE
31-97%
O
O
R
2
R
1
33
34
35
OSO
2
C
8
F
17
R
1
SCHEME 10.7
Ugi reaction-based synthesis of 1,4-benzodiazepine-2,5-diones.
sequence on
33
was different from that of
30
. The amino group attached to the amide
group instead of the ester group formed 1,4-benzodiazepine-2,5-diones
34
and led to
the formation of products
35
after the Suzuki linker cleavage reactions.
Zhang and coworkers recently employed fluorous benzaldehydes in the
synthesis of tetrasubstituted furans (Scheme 10.8) [36].
-Unsaturated ketones
36
were prepared by condensation of fluorous benzaldehydes
25
and acetophenones.
Mn(OAc)
3
- and Cu(OAc)
2
-promoted cycloaddition of
36
with 1,3-diketones under
a
,
b
O
10% NaOH
EtOH
O
O
O
CHO
R
3
R
1
R
2
R
2
R
1
15-30°C , 4 h
F-SPE
Mn(OAc)
3,
Cu(OAc)
2
OSO
2
C
8
F
17
OSO
2
C
8
F
17
μ
W 165°C, 25 min
25
36
F-SPE
75-90%
76-85%
B(OH)
2
R
1
R
2
O
R
4
COR
3
R
4
Pd(dppf)Cl
2
, Cs
2
CO
3
O
μ
W 130°C, 30 min
R
1
R
2
38
57-73%
O
COR
3
R
1
R
2
C
8
F
17
O
2
SO
O
O
NH
2
R
4
CO
2
R
3
37
NH
Pd(dba)
3
, JohnPhos
DBU, PhMe
O
R
4
39
μ
W 130°C, 30 min
45-69%
SCHEME 10.8
Fluorous benzaldehydes for the synthesis of tetrasubstituted furans.
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