Figures
R
S
R
S
CHO
8
R
S
S
S
S
CHO
CHO
9
10
b
c
d
e
R = MeO
R = EtO
R = NMe2
R = NEt2
d R = NMe2
g R = piperidino
Figure 1
21
a
b
c
d
R=H
R = MeO
R = EtO
R = NMe2
Table 1
Entry
R
Compound
2
Yield
Yield
(%)
Compound
4
Yield
(%)
Compound
3
(%)
Compound
5
Yield
(%)
Global
Yield
(%)
1
H
a
40
a
23
a
10
a
22
0.2
2
MeO
b
82
b
77
b
25
b
44
6.9
3
EtO
c
85
c
95
c
50
c
---
---
4
NMe2
d
95
d
59
d
99
d
44
24
5
NEt2
e
52
e
64
e
70
e
13
3.0
6
Pyrrolidino
f
99
f
50
f
99
f
10
4.9
22
Table 2
Entry
R
Compound
5
Yield
(%)
δH
(ppm)a
Reaction
time
(h)
IR ν
(cm-1)b
λ max (ε)
(nm)c
1
H
a
78
9.88
2
1654
382.5 (26,775)
2
MeO
b
53
9.87
12
1665
394.5 (27,936)
3
EtO
c
80
9.86
3
1672
395.5 (18,965)
4
NMe2
d
64
9.85
24
1657
424.0 (24,538)
65d
3d
5
NEt2
e
---
9.85
---
1652
435.5 (26,966)
6
Pyrrolidino
f
---
9.85
---
1645
433.0 (32,976)
23
Table 3
Entry
R
Compound
5
λ max
(nm)
Compound
8
λ max
(nm)
Compound
10
λ max
(nm)
1
H
a
382.5
a
----
a
287.0
2
MeO
b
397.0
b
385.0
b
345.0
3
EtO
c
398.0
c
383.0
c
345.0
4
NMe2
d
430.5
d
451.0
d
410.0
5
NEt2
e
442.0
e
463.0
e
----
6
Pyrrolidino
f
435.0
f
----
f
----
24
Schemes
O
H
O
POCl3 / DMF / 60 oC
CH3
R
Cl
R
1a-f
a
b
c
d
e
f
R
5a-b, d -f
S
CHO
O
R
S
ClCH2COCH3 / K2CO3
2a-f
3a-f
R=H
R = MeO
R = EtO
R = NMe2
R = NEt2
R = pyrrolidino
Na2S.9 H2O / DMF
S
Na2S.9 H2O / DMF
ClCH2CHO / K2CO3
Scheme 1
25
POCl3 / DMF / 60 oC
O
R
H
S
Cl
4a-f
B(OH)2
+
Br
S
CHO
S
DME / Pd(PPH3)4
Na 2CO3 (2M) / 80 oC / Ar
R
6a-d
7
R
CHO
5a-d
a
b
c
d
Scheme 2
S
S
R=H
R = MeO
R = EtO
R = NMe2
26