Biomedical Engineering Reference
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O
Me
O
cat. PBu 3
CH C 2 , rt
N
CO Et
2
NN
+
N
-
+
CO Et
2
Ar
7a
15a
16a
Ar= p -NO C H
Ar
26 4
PBu 3
PBu 3
O
O
+
PBu 3
15a
N
N
CO Et
-
-
2
N
N
CO Et
2
PBu 3
PBu 3
CO Et
2
+
Ar
Ar
11
23
24
SCHEME 4.6 Phosphine-catalyzed [3 + 2] annulations with azomethine imine.
O
R 2
R 2
O
Phosphin e
CH C 2 , rt
N
N N
+
+
N
R 1
CO Et
2
CO Et
2
15
R 1
7
16
SCHEME 4.7 Synthesis of highly functionalized tetrahydropyrazolopyrazolones.
TABLE 4.3 Highly Functionalized Tetrahydropyrazolopyrazolones
Phosphine
(20 mol%)
Time
(h)
Yield
(%)
R 1
R 2
Entry
1
Ph
H
PBu 3
24
97
2
4-OMe-Ph
H
PBu 3
30
85
3
4-CF 3 -Ph
H
PBu 3
24
98
4
3-NO 2 -Ph
H
PBu 3
24
97
5
2-Me-Ph
H
PBu 3
48
70
6
2-Naphthyl
H
PBu 3
24
96
7
4-Py
H
PBu 3
20
86
8
2-Furanyl
H
PBu 3
20
99
9
4-NO 2 -Ph
Me
PMe 3
20
96 a
10
4-NO 2 -Ph
t -Bu
PMe 3
24
98 a
11
4-NO 2 -Ph
2-Me-Ph
PMe 3
20
95
12
4-NO 2 -Ph
4-F-Ph
PMe 3
15
99
a At 40 C.
 
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