J. Chem. Sci.
(
2
0
2
0
)
1
3
2
:
3
8
P
a
g
e
3
o
f
9
3
8
2
.
1
7
–
2
.
2
3
3
(
m
,
, J
4
H
,
2
C
H
)
,
6 Hz, J
2
.
5
1
(
d
6 Hz
,
4
H
,
2
C
H
)
2
,
4
.
7
8
(
s
,
1
, J
H
,
2
.
4
p
1
4
-
(
2
-
c
h
l
o
r
o
p
h
e
n
y
l
)
-
1
4
H
-
d
i
b
e
n
z
o
[
a
,
j
]
x
a
n
t
h
e
n
e
(
4
d
)
:
2
-
1
1
C
H
)
,
7
.
4
(
d
=
9
.
=
.
,
2
H
,
A
r
H
)
,
7
.
5
4
(
d
=
I
R
(
K
B
r
,
m
c
x
m
)
:
3
0
5
5
,
- d6
2
9
2
0
,
1
6
2
5
,
1
4
1
(
0
,
1
2
5
6
.
H
m
a
6
.
6
H
z
,
J
=
1
.
6
H
z
,
2
H
,
A
r
H
)
.
N
M
R
(
3
0
0 MHz
1
,
D
M
S
O
;
p
p
m
)
:
d
5
.
6
9
s
,
1
H
,
C
H
)
,
5
.
8
2
–
7
.
6
5
(
m
,
6
H
,
A
r
H
)
.
2
.
4
h
ooctahydroxanthene ( 3h
3,3,6,6-Tetramethyl-9-(4-Hydroxyphenyl)-1,8-diox-
-
1
)
:
I
R
(
K
B
r
,
m
c m
x
)
:
3
4
0 MHz
9
8
,
3
0
7
8
,
2
.
4
q 14-(4-Bromophenyl)-14H-dibenzo[a,j]xanthene ( 4e) :
1
m
a
1
-
1
2
9
2
9
,
1
7
1
9
,
1
6
4
5
,
1
4
6
5
,
1
1
6
6
.
H
N
M
R
(
3
0
,
,
D
M
S
O
-
I
R
(
MHz
K
B
r
,
m
c m
x
)
:
3
0
3
0
,
1
6
2
4
,
1
4
2
9
,
1
2
5
4
.
H
N
M
R
(
3
0
0
m
a
d6
,
p
p
m
)
:
d
1
.
0
0
(
s
,
6
H
,
2
C
H
)
,
1
.
1
1
(
s
,
6
H
2
C
H
1
)
,
,
,
,
D
M
S
O
-
d
,
p
p
m
)
:
d
6
.
6
3
(
s
,
1
H
,
C
H
)
,
7
.
3
2
–
8
.
4
4
(
m
,
3
3
6
2
.
1
2
–
2
.
1
8
(
m
,
, j
4
H
=
,
2
C
H
)
,
2
.
4
5
(
s
,
4
H
,
2
C
H
)
, j
,
4
.
6
1
(
s
,
H
1
6
H
,
A
r
H
.
)
.
2
2
C
A r H ) .
H
)
,
6
.
7
7
(
d
8
H
z
,
2
H
,
A
r
H
.
)
,
6
.
9
3
(
d
=
8
H
z
,
2
H
2
.
4
r 14-(4-Nitrophenyl)-14H-dibenzo[a,j]xanthene (4f
-
)
:
I
R
1
1
(
i 3,3,6,6-Tetramethyl-9-(4-Methoxyphenyl)-1,8-dioxooc- MHz
K
B
r
,
m
c
m
)
:
3
0
6
5
,
1
6
2
1
,
1
4
5
8
,
1
2
5
0
.
H
N
M
R
(
3
0
0
m
a
x
2
tahydroxanthene ( 3i
1
.
4
,
6 H , A r H ) .
D
M
S
O
-
d
,
p
p
m
)
:
d
6
.
6
2
(
s
,
1
H
,
C
H
)
,
7
.
4
6
–
8
.
3
1
(
m
,
6
-
1
)
:
I
,
R
1
(
K
B
r
,
m
c
x
m
)
:
3
0
0 MHz
5
0
,
2
9
5
8
,
1
m
a
1
6
5
8
,
1
6
2
5
,
1
4
3
9
,
1
2
(
6
1
1
9
5
.
H
N
M
R
(
3
0
,
,
D
M
S
O
-
2
.
4
s
1
4
-
(
3
-
N
i
t
r
o
p
h
e
n
y
l
)
-
1
4
H
-
d
i
b
e
n
z
o
[
a
,
j
]
x
a
n
t
h
e
n
e
(
4
g
)
:
I
R
d6
,
p
p
m
)
:
d
1
.
0
0
s
,
6
H
,
2
C
H
)
,
1
.
1
1
(
s
,
6
H
2
C
H
3
)
,
3
3
-
1
1
( K
MHz
B
r
,
m
c
m
)
:
3
0
7
0
,
1
6
1
9
,
1
4
,
5
2
,
1
2
5
4
.
H
N
M
R
4
(
3
0
0
m
a
x
2
.
2
0
–
2
.
2
2
(
m
,
4
H
,
2
C
H
)
,
2
.
4
7
(
s ,
, J
4
H ,
9 Hz
2
C
H
)
,
3
.
7
4
(
s
,
H
,
2
2
,
D
M
S
O
-
d
,
p
p
m
)
:
d
6
.
6
4
(
s
1
H
,
C
H
)
,
7
.
2
9
–
8
.
4
(
m
,
6
O
C
H
)
= 9 Hz, 2 H , A rH ) .
,
4
.
7
1
(
s
,
1
H
,
C
H
)
,
6
.
7
6
(
d
=
,
2
H
,
A
r
H
)
,
7
.
2
2
3
1
6
H
,
A
r
H
)
.
(
d
,
J
2
.
4
t 14-(4-Methoxyphenyl)-14H-dibenzo[a,j]xanthene ( 4h
-
)
:
2
.
4
j
3
,
3
,
6
,
6
-
T
e
t
r
a
m
e
t
h
y
l
-
9
-
(
3
-
M
e
t
h
o
x
y
p
h
e
n
y
l
)
-
1
,
8
-
d
i
o
x
o
o
c
-
1
I
1
R
(
K
B
r
,
m
c m
x
)
:
3
0
6
0
,
1
6
- d6
3
4
,
1
4
5
7
,
1
3
9
9
,
1
2
4
7
,
1
2
0
0
.
-
1
m
a
tahydroxanthene ( 3j
1
)
:
I
,
R
1
(
K
B
r
,
m
c
x
m
)
:
3
0
0 MHz
2
0
,
2
9
5
0
,
m
a
H
N
M
R
(
3
0
0 MHz
1
,
D
M
S
.
O
,
p
p
m
)
:
d
6
.
4
0
(
s
,
1
H
,
C
H
)
,
1
6
5
0
,
1
6
1
8
,
1
4
5
9
,
1
2
3
5
1
6
0
.
H
N
M
R
(
3
0
,
,
D
M
S
O
-
7
.
3
2
–
8
.
3
5
(
m
,
6
H
,
A
r
H
)
d6
,
p
p
m
)
:
d
0
.
9
9
(
s
,
6
H
,
2
C
H
)
,
1
.
1
2
(
s
,
6
H
2
C
H
)
3
,
3
2
.
3
0
3
–
2
.
4
5
(
m
,
4
H
,
2
C
H
)
,
2
.
5
4
–
2
.
7
1
(
m
,
4
H
,
2
, J
C
H
=
)
,
.
3
.
8
1
2
2
2
.
4
u 9-(4-Formylphenyl)-1,8-dioxooctahydroxanthene
-
:
I
R
1
(
s
,
H
,
6 Hz
O
C
H
)
,
4
.
8
3
(
s
,
1
H
,
C
H
)
,
6
.
6
9
-
6
.
7
1 (
, J
d
d
8
0
H
z
,
3
(
K
B
r
,
m
c
x
m
)
:
3
0
2
1
,
2
9
6
8
,
0 MHz
2
8
4
5
,
2
7
5
6
,
1
6
6
1
,
1
6
2
0
,
m
a
1
J
=
1
.
,
1
H
)
,
6
.
8
9
-
6
.
9
5
(
m
,
2
H
)
,
7
.
1
7
(
t
=
8
.
0
H
z
,
1
H
)
.
1
6
5
4
5
4
,
1
1
9
7
.
H
N
M
R
6
(
3
0
,
C
D
C
l
,
p
p
m
)
:
d
0
.
9
1
(
s
)
,
3
H
,
2
C
H
)
,
1
.
0
7
(
s
,
H
,
2
C
H
)
,
2
.
0
9
-
2
.
3
5
(
m
,
8
H
,
4
C
H
,
3
3
2
2
.
4
k
ooctahydroxanthene ( 3k
3,3,6,6-Tetramethyl-9-(2-Methoxyphenyl)-1,8-diox-
1
-
.
3
(
s
,
1
H
,
C
H
,
)
,
6
.
8
5
(
d
,
1
H
,
A
r
H
)
,
7
.
0
6
(
d
,
1
H
,
A
r
H
)
,
7
.
6
3
)
:
I
R
(
K
B
r
,
m
c m
x
)
:
3
0
0 MHz
1
5
,
2
9
5
0
,
m
a
1
3
(
d
3
,
1 H
0 MHz
,
A
r
,
H
)
9
.
7
8
(
d
,
1
H
,
C
H
)
,
1
2
1
.
6
5
8
,
(
s
,
1
H
)
.
C
N
M
R
1
1
6
6
0
,
1
6
2
3
,
1
4
9
0
,
1
2
5
0
,
1
1
9
,
8
.
H
N
M
R
(
3
0
,
,
D
M
S
O
-
(
0
C
D
C
l
,
p
p
m
)
: d
9
2
7
.
4
5
,
7
.
2
9
.
6
2
,
3
1
.
4
4
,
3
2
8
1
6
9
.
.
.
4 9,
63 ,
34 ,
3
d6
,
p
p
m
)
:
d
0
.
9
7
(
s
,
6
H
2
C
H
)
,
1
.
1
1
(
, j
s
,
6
H
2
C
H
4
)
,
3
3
3
1
1
2
.
3
9
7
5
,
3
,
3
.
3
3
,
4
6
.
4
1
,
4
6
.
9
,
1
1
5
.
1
3
,
1
1
5
.
2
7
,
1
1
5
.
5
5
,
1
1
2
.
1
4
–
2
.
2
3
(
m
,
4
H
,
2
C
H
)
,
2
.
3
9
–
2
,
.
4
8
(
d
=
1
7
.
4
,
H
,
2
2
9
6
0
.
.
4
4
1
1 9 1 .7 8 .
2
7
.
4
4
,
1
2
9
.
7
9
,
1
3
4
.
3
2
,
1
3
5
.
5
,
1
4
5
.
9
3
,
2
Hz
C
H
)
,
3
.
7
9
(
s
,
3
H
,
O
C
H
, J
) , 4
3
.
8
7
(
s
1
H
,
C
H
)
2 Hz
,
6
.
7
7
1
(
d
,
J
=
8
2
,
,
1
H
,
A
r
H
)
,
6
.
8
9
(
,
d
t
=
7
.
4 Hz, J
, J
=
1
.
,
H
,
A
r
H
)
,
. 6 Hz
7
1
.
1
2
(
m
,
H , A r H ) .
1
H
,
A
r
H
)
7
.
4
3
(
d
d
=
7
.
4
H
z
,
J
=
1
3. Results and Discussion
1 Characterization of the catalyst
2
1,8-dioxooctahydroxanthene ( 3I
.
4
l
3,3,6,6-Tetramethyl-9-(4-Hydroxy-3-methoxyphenyl)-
-
1
)
:
I
R
(
K
B
r
,
m
c
x
m
)
:
m
a
3
.
1
3
MHz
6
9
4
,
3
0
6
5
,
2
9
- d6
7
2
,
1
6
6
5
,
1
6
0
8
,
1
4
1
0
,
1
1
6
9
.
H
N
M
R
(
3
0
0
,
D
M
S
O
,
p
p
m
)
:
d
1
.
0
0
(
s
,
6
H
,
2
C
H
)
,
1
.
0
9
(
s
,
6
3
H
,
3
T
h
w
e
F
n
R
e
a
,
r
b
t
o
h
n
a
s
R
1
r
n
o
u
p
c
,
h
a
t
E
o
p
e
e
r
u
t
r
D
i
c
e
S
l
z
e
e
a
h
s
w
e
r
e
(
E
l
F
M
R
0
a
-
o
e
a
d
e
)
d
w
i
n
z
e
o
a
l
i
r
t
a
e
c
X
a
n
e
d
d
t
b
h
y
e
2
C
H
)
,
2
.
2
0
(
s
,
4
H
,
2
,
C
H
)
,
2
.
4
4
(
s
,
4
H
,
2
C H ) , 3
2
.
8
8
(
s
,
H
,
3
2
n
e
n
o
t
r
o
l
i
t
e
- X
t e c h n i q u e s .
a
s
c
h
t
e
r
i
z
O
C
H
) ,
1 Hz
4
.
6
5
(
s
,
1
H
C
H
) ,
, J
5
.
4
6
( s
2 Hz
,
1
H
)
,
6
.
5
3
-
6
.
5
8
( d
, J
d
,
J
=
3
F
T
-
I
X
e
D
n
e
d
F
S
T
3
t
d
1
2
.
0
,
8
.
,
1
H
)
,
6
.
7
1
(
d
=
8
.
,
1
H
)
,
7
.
0
0
(
d
=
2
.
0
F
e
i
g
u
s
w
s
a
s
O
t
-
I
s
c
p
m
d
e
c
t
r
a
a
m
o
o
f
F
1
e
-
X
c
c
a
m
e
t a
- 1
l
y
a
s
t
.
e
Hz, 1 H ) .
-
1
T
h
o
s
e
v
e
d
e
k
y
s
a
t
4
r
4
n
d
m
p
s
e
6
r
2
i
T
a
O
c
0
c
h
t
r
g
p
h
2
.
4
m 14-(Phenyl)-14H-dibenzo[a,j]xanthene ( 4a
-
x
)
:
I
R
(
K
B
r
,
,
,
a
t
t
r
i
r
b
u
e
d
t
o
t
t
h
h
m
H
b
m
e
i
c
n
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o 14-(3-chlorophenyl)-14H-dibenzo[a,j]xanthene ( 4c
-
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:
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