A Facile and Effective Procedure for Synthesis of Polyfunctionalized Bis (imidazolyl) Pyrrole/Imidazolyl Indole from Pyrrole/Indole with Arylglyoxals and N-aryl amidines

Article abstract of DOI:10.1002/jhet.3652

Heterocyclic systems containing bis (imidazolyl) pyrrole or imidazolyl indole moieties were synthesized by heterocyclization of pyrrole or indole with arylglyoxal monohydrates and N-aryl amidines in ethanol catalyzed by FeCl₃ at room temperature. The paper reports a facile, efficient, and environmentally friendly protocol for the synthesis of new products. Products were isolated by simple filtration, and their structures were established from their spectroscopic data.

Full text of DOI:10.1002/jhet.3652

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Table 1
Table 2
T
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m
s
p
y
r
r
l
s
e
i
t
h
a
r
y
l
g
l
y
o
m
x
a
o
o
d
a
t
e
s
a
n
d
s
t
i
r
r
i
n
g
,
t
h
e
a
m
i
d
i
n
e
d
e
r
i
v
a
t
i
v
e
s
(
1
m
m
o
l
)
w
e
r
e
a
a
d
d
e
b
l
t
t
N
d
r
y
i
d
i
n
t
a
f
f
o
r
d
n
o
u
t
i
t
t
e
i
n
d
o
l
e
t
t
h
e
e
m
r
p
e
e
a
a
c
t
e
t
u
d
i
o
r
n
e
b
m
i
r
x
t
6
u
r
e
h
,
.
.
T
A
h
f
e
t
r
s
o
l
t
l
u
h
t
t
e
i
i
o
n
w
a
s
o
i
s
n
t
i
r
w
r
e
a
e
d
s
t
a
m
i
n
d
d
t
r
i
v
a
t
i
v
.
r
a
f
o
e
r
r
e
a
c
t
i
c
o
m
s fi
p
l
r
e
e
t
r
t
e
e
h
(
i
n
d
i
c
t
y
T
L
C
)
t
h
e
e
s
u
n
g
p
r
e
c
p
i
t
a
t
w
a
o
p
f
f
a
n
d
w
a
s
h
e
d
w
i
t
h
d
i
e
t
h
y
l
e
t
h
e
r
(
2
0
m
L
)
t
o
a
f
f
o
d
e
CONCLUSIONS
u
r
e
p
r
o
d
u
c
t
.
Selected spectral data. 2,5-Diphenyl-4-(5-(2,5-diphenyl-1-
p-tolyl-1H-imidazol-4-yl)-1H-pyrrol-2-yl)-1-p-tolyl-1H-
I
n
m
n
c
e
a
e
o
n
z
o
c
e
l
u
o
s
i
f
p
o
n
a
r
l
,
w
e
w
e
o
f
o
u
c
n
d
s
a
s
s
o
a
i
m
f
p
h
y
l
i
l
e
g
a
h
n
d
e
f
f
fi
c
c
r
e
i
t
o
s
e
n
n
t
m
e
z
r
t
e
r
h
d
o
o
o
d
b
t
i
o
o
s
r
c
e
e
f
t
s
y
t
h
s
i
n
e
l
a
l
y
u
n
f
i
o
a
l
i
imidazole (7a).
Y
( ῡm
i
e
, c
x
N
,
l
d
:
8
6
%
)
,
N
;
c
r
3
.
e
4
3
0
a
3
1
m
4
;
6
p
(
H
%
o
N
,
.
w
H
d
)
.
e
,
4
-
r
;
1
;
m
.
p
9
,
.
1
(
1
D
3
9
–
1
N
%
O
4
)
0
.
.
-
1
(
i
i
d
z
w
l
y
l
)
y
r
g
p
t
s
e
o
l
o
x
e
m
r
a
n
i
m
i
d
z
o
l
i
n
d
o
l
e
m
p
y
l
e
°
C
.
I
R
(
K
B
r
)
m ꢀ
:
5
8
C
¼
a
i
n
d
o
l
i
a
i
t
h
a
h
o
e
r
y
l
y
l
s
a
n
d
N
-
a
r
y
l
t
l
a
m
i
d
i
n
i
t
n
a
i
a
l
c
h
T
t
e
l
o
l
i
C
a
l
c
d
.
f
o
r
(
C
H
3
)
.
:
C
;
8
4
1
5
5
N
N
0
.
2
4
4
8
7
5
1
m
a
s
e
y
p
e
d
a
i
n
t
e
f
i
r
e
s
c
e
o
f
F
e
C
a
s
a
n
a
c
a
b
s
n
l
y
s
t
o
u
c
.
h
h
o
n
F
o
u
n
d
:
C
,
8
4
.
1
6
;
H
5
2
1
,
.
5
H
M
R
(
M
S
3
d
t
t
i
v
n
t
a
g
m
a
a
e
s
a
h
i
s
e
t
h
o
l
e
d
a
c
l
n
r
e
h
c
e
e
e
v
a
i
l
a
i
l
t
y
f
s
e
f
d6
,
4
7
o
H
0
(
f
0
1
p
M
H
)
C
e
: δ
H
=
o
2
f
.
p
(
1
y
1
N
9
r
H
(
3
l
d
)
H
,
s
5
,
C
H
)
,
H
2
,
.
2
d
1
(
3
H
,
s
=
,
C
8
H )
H z
,
,
,
Z
3
3
4
a
r
t
i
n
g
t
r
n
a
l
,
n
i
e
e
u
n
i
t
r
a
r
e
a
t
i
o
n
g
n
o
n
d
i
t
i
o
n
v
c
,
t
t
h
e
4
.
8
H
,
s
,
r
o
e
)
,
.
0
3
( 1
8
,
J
H
H
4
h
a
n
d
d
o
l
s
n
a
n
v
r
o
m
s
n
t
a
l
y
r
d
s
o
l
e
a
,
e
n
x
o
l
e
C
H
y
r
r
o
l
)
,
6
.
0
0
s
,
H
D
,
J
=
H
z
,
N
H
)
,
6
.
2
7
(
1
H
H
H
e
l
s
,
d
s
i
m
p
l
o
l
a
t
i
o
a
p
u
r
i
fi
t
i
o
t
h
e
s
,
N
d
)
,
6
.
5
0
(
1
H
,
,
,
6
.
8
3
-
7
.
5
2
(
2
7
H
H
,
m
)
,
a
r
o
m
a
.
t
8
i
3
c
1
3
r
o
u
c
t
s
.
h
y
r
o
g
e
n
s
)
,
C
-
N
M
R
(
M
S
O
-
d
,
1
0
0
M
:
δ
=
2
0
6
Z
J
o
u
r
n
a
l
o
f
H
e
t
e
r
o
c
y
c
l
i
c
C
h
e
m
i
s
t
r
y
D
O
I
1
0
.
1
0
0
2
/
j
h
e
t

A
F
a
l
c
y
i
l
l
e
)
a
n
r
d
r
E
f
f
/
e
c
t
i
i
d
v
a
e
z
P
o
r
l
o
y
c
l
e
d
d
u
o
r
e
f
o
r
o
S
m
y
n
P
t
y
h
r
e
r
s
o
i
l
s
e
o
f
P
o
l
l
e
y
w
f
u
i
n
c
t
A
i
o
r
n
y
a
l
l
g
i
z
e
o
d
x
B
i
s
s
O
c
t
o
b
e
r
2
0
0
1
9
(
,
6
1
i
m
i
d
a
z
o
P
y
o
l
e
Im
I
n
l
e
f
r
/
I
n
d
o
t
h
l
y
a
l
a
:
n
d
2 77 7
N
-
a
r
y
l
a
m
i
d
i
n
e
s
(
C
H
4
9
)
,
2
.
8
9
.
2
2
(
6
C
,
5
7
H
1
,
)
3
2
9
5
2
9
N
.
,
5
6
,
9
8
2
1
.
8
2
5
,
9
1
(
C ¼
C
)
,
3
,
1
2
8
7
4
.
9
.
6
1
2
7
,
(
,
1
1
r
2
4
.
.
a
6
1
t
4
6
i
,
,
c
7
8
C
5
N
(
M
(
0
.
.
1
6
7
%
;
H
H
,
4
.
0
M
5
;
R
H
N
(
,
,
D
s
=
,
8
M
,
.
5
S
2
O
H
H
%
- d6
.
F
,
5
C
o
4
u
0
1
n
0
d
C
,
H
,
r
6
9
: δ
.
8
6
=
H
6
;
H
,
4
.
3
6
;
N
s
,
,
,
,
3
1
1
1
2
2
.
.
9
2
3
4
n
,
,
s
1
2
5
1
6
4
9
.
.
4
1 2
,
7
.
1
2
8
.
0
9
1
2
2
9
7
H
2
H
.
-
6
N
(
M
)
2
.
1
5
(
3
H
,
Z
.
3
2
.
6
3
.
7
4
,
1
0
.
a
o
m
)
,
(
2
.
1
3
C
)
,
.
1
(
1
H
y
s
,
C
o
f
p
y
r
H
r
o
,
l
e
)
3
3
4
c
a
r
b
o
)
,
1
5
(
C
¼
)
.
.
4
1
H
,
1
d
, JH
(
8
N
d
z
,
H
7
,
2
2
5
o
f
p
r
o
l
e
)
,
.
1
1
(
1
b
s
H
5-(4-Fluorophenyl)-4-(5-(5-(4-fluorophenyl)-2-phenyl-1-p-
tolyl-1H-imidazol-4-yl)-1H-pyrrol-2-yl)-2-phenyl-1-p-tolyl-1H-
imidazole (7b).
)
,
6
.
3
1
m
H
a
2
2
5
,
t
s
H
r
C
6
)
,
6
.
4
(
1
H
,
s
,
N
(
H
)
,
6
O
.
7
7
–
7
1
.
6 1
00
5 9
1
3
2
4
H
H
,
)
m
,
a
r
o
i
c
h
y
o
H
,
,
g
e
n
,
s
)
C
-
N
(
7
1
M
C H ) ,
3
.
.
R
D
M
S
-
d
,
6
Y
i
e
c
l
d
:
7
8
:
0
5
%
3
9
%
;
w
h
i
(
4
H
t
e
p
H
0
N
o
w
d
6
,
e
0
9
r
;
m
.
p
.
1
6
3
–
1
6
l
:
4
4
c
°
.
,
0
6
f
,
c
2
,
: δ
)
0
8
=
0
,
,
.
7
8
(
)
2
3
0
9
3
i
.
8
5
9
8
1
4
.
.
.
5
8
0
0
8
4
,
9
8
.
Z
3
1
C
.
I
R
(
K
B
r
)
(
ῡ
,
m ꢀ
)
.
4
6
H
.
5
,
N
)
,
1
8
(
C
¼
N
)
o
.
u
C
a
d
C
m
a
x
C
¼
C
,
,
,
1
1
1
2
2
4
9
.
.
9
4
9
1
1
2
4
.
9
0
1
1
1
7
1
.
.
,
,
c
1
2
6
9
,
,
)
1
1
1
2
3
6
,
,
1
1
(
2
9
.
.
0
N )
0
9
1
,
,
.
f
o
r
.
H
H
r
H
d
H
7
0
(
C
H F N ) :
8 3 5 2 5
C
,
8
0
;
.
9
;
N
.
(
7
3
%
.
F
n
d
4
1
1
2
3
9
4
.
.
5
5
1
3
0
.
7
1
3
5
7
3
2
1
7
9
8
8
;
H
,
=
H
4
2
o
0
.
7
1
;
N
,
9
.
5
-
2
,
M
R
D
,
=
M
s
S
O
C
H
3
-
d
,
0
6
3
6
.
,
1
4
1
.
6
(
a
r
o
m
a
t
c
a
r
b
o
n
s
,
1
.
0
9
C
¼
M
)
:
δ
.
f
7
1
9
p
(
3
r
,
H
,
s
,
C
H
)
,
.
2
1
, JH
(
3
H
,
8
6
m
)
4
.
6
H
z
5
)
,
4
.
8
Z
3
3
5-(4-Bromophenyl)-4-(5-(5-(4-bromophenyl)-2-phenyl-1-p-
tolyl-1H-imidazol-4-yl)-1H-pyrrol-2-yl)-2-phenyl-1-p-tolyl-1H-
4
(
1
,
o
s
,
)
6
C
,
.
y
r
o
l
e
d
N
R
9
)
,
5
.
0
2
(
1
H
4
d
H
,
(
r
=
1
1
r
C
H
o
s
i
H
4
p
y
r
l
e
6
2
.
(
1
H
, JH
H
=
4 –
O
8
1
1
z
,
N
2
H
6
M
)
,
4
)
H
,
,
.
1
H
,
imidazole (7f).
C
f
6
M
(
p
N
h
(
1
1
c
Y
i
e
l
d
:
8
7
%
;
c
r
e
a
(
m
p
o
)
w
,
d
e
r
;
m
.
p
.
1
6
8
–
1
6
9
°
H
1
N
)
,
5
(
1
H
,
C
C
,
0
s
,
)
,
6
.
8
7
.
5
4
(
,
a
o
m
a
t
.
I
R
(
K
B
r
)
(
ῡ
, c
x
m ꢀ
)
:
3
4
5
2
N
H
1
5
8
7
(
C
¼
N
)
.
C
a
l
c
d
.
,
m
a
1
3
h
y
r
o
g
e
n
s
)
,
-
N
M
) ,
3
8
1
(
.
,
D
2
M
0
S
9
- d6
2
,
9
,
(
1
0
0
H
1
: δ
.
6
2
0
.
8
o r ( C H B r N ) : C , 6 8 . 5 0 ; H , 4 . 1 9 ; N , 8 . 3 2 % . F o u nd : C
4 8 3 5 2 5
Z
1
(
C
)
,
2
0
.
8
8
1
6
7
.
3
2
(
1
H
1
,
5
9
8
N
,
.
7
3
0
C
¼
C
5
1
,
2
9
2
8
3
7
,
(
,
2
5
.
.
a
0
0
t
1
4
i
8
.
3
9
;
H
,
4
.
3
2
1
;
N
,
H
8
.
4
5
C
%
.
H
-
N
M
1
, JH
z
6
1
R
3
(
H
D
M
s
S
O
- d6
3
,
4
0
0
7
3
1
1
2
3
.
.
6
6
5
3
n
,
,
s
1
2
5
4
.
2
.
5
1 2
,
9
.
1
2
9
.
3
1
2
3
0
,
c
H
)
s
l
:
δ
=
2
o
.
f
0
9
p
(
(
3
,
s
,
H
)
,
2
.
2
(
,
=
)
,
4
6
C
H
)
,
4
.
8
Z
3
4
.
3
3
.
7
9
.
1
3
,
2
.
a
o
m
1
y
H
,
o
,
C
H
6
3
y
r
r
o
l
e
)
,
5
.
0
3
(
1
H
,
d
H
H
z
,
C
H
o
f
H
4
c
a
r
b
o
)
,
1
7
1
(
C
¼
)
.
r
H
d
r
e
)
,
.
1
1
H
,
d
N
R
, JH
H
=
4 –
O
.
7
1
8
7
,
N
H
6
M
,
,
4
,
,
.
4
1
(
1
H
,
s
,
H
2-(2-Chlorophenyl)-4-(5-(2-(2-chlorophenyl)-5-(4-
fluorophenyl)-1-p-tolyl-1H-imidazol-4-yl)-1H-pyrrol-2-yl)-5-(4-
fluorophenyl)-1-p-tolyl-1H-imidazole (7c).
)
,
6
.
5
(
1
H
C
C
5
0
,
s
,
M
)
,
6
.
8
.
5
(
2
H
m
,
a
r
o
m
a
t
i
c
1
3
y
C
2
3
a
r
o
)
g
,
8
8
e
n
s
)
,
-
N
(
D
M
S
-
d
,
0
0
H
1
1
.
)
:
δ
=
1
1
2
0
.
7
7
6
Z
Y
( ῡm
i
e
l
d
:
8
4
%
;
:
H
7
1
2
0
.
8
2
(
5
.
.
H
) ,
3
8
7
7
4
.
8
9
1
8
,
2
,
9
8
1
0
3
2
,
8
(
C ¼
C
)
2
3
1
5
0
9
.0
9
,
2
5
.
.
2
5
6
,
3
1
c
r
e
3
.
6
a
m
9
0
%
p
N
o
w
d
e
r
;
6
2
m
.
p
.
1
4
8
–
1
5
C
.
-d6
) ,
z
(
0
a
F
,
5
C
H
a
°
C
d
u
.
I
R
(
K
B
r
)
, c
x
m ꢀ
)
a
.
8
,
1
2
8
.
2
3
,
5
5
1
2
9
.
3
,
9
.
1
3
0
,
.
2
9
.
4
5
,
(
3
1
4
,
3
7
8
4
3
.
(
;
H
,
H
)
,
1
2
M
3
0
4
(
,
C
¼
N
)
.
l
c
.
n
0
1
f
o
r
(
C
H
.
C
l
F
,
N ) :
5
C
,
,
,
,
,
,
4
8
3
3
2
2
.
7
,
1
3
,
1
3
.
7
.
7
0
1
5
a
r
o
m
a
t
i
c
1
5
H
4
-
6
d
.
N
(
, JH
z
(
;
R
H
N
(
,
8
.
8
8
%
o
4
d
0
:
M
C
,
7
)
3
: δ
3
5
;
=
H
4
.
3
6
;
N
r
b
o
n
s
)
,
1
6
4
(
C
¼
N
)
.
1
.
2
1
D
M
S
C
8
O
H
H
3
a
: δ
1
,
H
2
.
1
5
(
3
H
,
s
Z
2-Phenyl-4-(5-(2-phenyl-1,5-dip-tolyl-1H-imidazol-4-yl)-1H-
pyrrol-2-yl)-1,5-dip-tolyl-1H-imidazole (7g).
C
H
)
,
(
=
7
S
,
2
5
.
1
s
,
.
1
(
1
H
,
s
,
C
H
o
.
f
0
H
p
y
(
r
r
o
l
e
)
Y
i
e
l
d
:
7
7
%
)
;
:
3
3
4
1
.
1
4
–
I
R
(
f
,
m ꢀ
5
.
2
4
H
,
8
4
-d6
=
,
m
,
1
m
H
,
t
2
4
5
1
o
,
f
N
h
6
p
y
r
ro
l
4
e
e
)
,
6
6
1
H
,
d
b
3
8
9
C
C
r
4
4
.
o
w
4
n
p
o
w
d
e
r
;
m
.
p
6
1
N
%
6
)
.
5
.
F
°
C
o
0
7
r
,
C
a
u
.
l
n
K
B
r
(
.
)
C
1
=
(ῡm
,
c
H
a
x
4JH
H
,
2
1
N
H
0
H
,
)
6
.
4
s
c
0
H)
,
6
.
8
n
(
1
,
s
,
N
H
)
6
6
%
(
N
H
,
H
)
,
1
1
5
;
8
8
(
9
C
¼
c
d
:
.
C
o
r
H
N ) :
5
C
N
s
,
,
,
,
H
5
0
4
1
1
3
6
.
7
M
.
4
4
6
–
.
O
6
4
0
,
r
o
i
y
d
r
o
g
s
)
,
0
C
-
N
M
H
.
.
R
.
3
;
H
5
.
8
M
3
1
N
R
,
(
.
8
C
4
d
8
: δ
C
1
4
3
;
H
,
8
5
(
.
6
3
;
1
(
D
,
M
H
)
Z
=
.
7
(
C
H
,
2
1
)
,
2
5
1
1
.
8
3
,
,
(
(
C
)
,
,
,
9
H
H
6
.
-
N
C
D
l
,
4
0
M
H
z
)
2
.
1
3
H
,
,
3
3
3
9
1
1
4
2
3
0
4
9
3
9
8
.
6
5
.
3
(
,
C
¼
C
9
1
)
,
6
7
1
3
1
,
.
8
,
0
3
1
1
4
.
0
1
1
1
.
2
7
3
1
1
r
2
4
3
1
t
0
2
i
)
)
,
,
2
.
2
0
3
(
H
H
r
,
,
s
,
C
H
)
,
f
2
p
(
.
2
(
o
s
3
H
,
s
,
H ) ,
(
.
2
.
2
9
(
3
H
s
3
3
3
4
.
.
,
,
1
2
7
1
8
4
2
1
,
2
.
4
2
9
.
,
8
1
3
0
.
0
,
4
1
3
.
7
5
3
2
4
.
8
(
s
,
C
H
o
5
y
r
l
e
,
)
,
5
H
.
0
1
1
H
7
,
d
,
J
=
4
3
H
H
.
4
8
3
.
0
3
.
8
0
,
2
.
a
o
m
a
c
H
z
,
C
H
o
f
p
y
r
o
l
e
)
,
6
.
0
1
H
N
)
,
6
(
1
H
,
s
,
N
H
)
,
c
a
r
b
o
n
s
)
,
1
6
0
.
4
4
(
C
¼
N
)
.
6
h
.
y
4
d
H
5
2
6
r
(
1
n
0
1
H
,
,
s
,
C
C
N
H
)
R
9
7
,
6
D
.
M
7
7
–
7
.
5
1
,
(
1
(
2
0
C
8
6
H
M
,
m
,
a
r
o
2
2
3
m
0
a
t
i
7
c
1
3
5-(4-Chlorophenyl)-4-(5-(5-(4-chlorophenyl)-2-phenyl-1-p-
tolyl-1H-imidazol-4-yl)-1H-pyrrol-2-yl)-2-phenyl-1-p-tolyl-1H-
imidazole (7d).
o
)
g
e
s
)
-
N
M
(
.
S
O
-
d
1
0
H
1
3
1
)
:
δ
=
1
1
.
3
6
Z
(
C
,
2
.
6
2
.
(
H
) ,
3
5
5
2
,
2
m
9
8
.
3
7
,
C
¼
)
,
2
4
.
2
2
7
8
,
,
4
.
7
9
N )
6
9
,
,
.
3
Y
i
e
l
d
:
c
8
4
%
)
;
c
r
3
7
9
e
4
6
a
5
.
m
0
p
(
;
%
o
N
H
.
w
H
d
)
4
e
,
r
;
1
m
.
p
7
N
.
1
(
,
D
s
=
6
8
–
1
N
%
O
6
)
9
.
.
-
,
,
,
1
1
2
3
.
.
3
9
1
4
,
,
2
3
8
4
1
4
,
1
2
8
.
0
,
1
9
.
0
1
2
9
.
7
n
,
1
,
0
.
6
0
.
1
°
C
.
l
u
,
I
R
(
o
C
M
K
B
r
)
( ῡm
H
8
,
m ꢀ
:
5
8
C
¼
a
x
1
.
6
9
,
1
3
6
.
6
6
(
a
r
o
a
t
i
c
c
a
r
b
o
s
)
6
5
.
8
(
C
¼
C
F
d6
4
a
o
c
n
4
7
d
d
0
(
f
.
:
0
1
f
r
,
(
C
C
l
N
)
:
C
,
,
s
5
9
,
.
6
9
;
9
.
3
0
2-(2-Chlorophenyl)-4-(5-(2-(2-chlorophenyl)-5-(4-
4
8
3
5
2
5
1
7
6
)
C
e
.
3
;
=
o
H
,
4
.
7
8
;
N
.
4
5
H
3
=
H
-
N
M
3
R
H
(
M
S
methoxyphenyl)-1-p-tolyl-1H-imidazol-4-yl)-1H-pyrrol-2-yl)-5-
(4-methoxyphenyl)-1-p-tolyl-1H-imidazole (7h).
w
Y
( ῡm
i
e
l
d
:
8
6
%
;
:
,
,
,
,
H
s
:
δ
2
.
1
9
(
3
H
,
,
C
)
,
2
.
2
d
,
6
M
,
,
4
1
(
,
,
C
4
H
)
Z
3
3
1
.
1
1
–
B
r
mꢀ
)
4
h
i
4
t
2
9
%
e
p
N
H
.
2
o
H
w
)
,
H
6
f
5
9
d
,
4
-
e
r
;
m
.
p
3
1
3
C
.
2
°
C
d
u
0
.
.
d
0
6
d
4
7
I
R
r
(
(
K
C
)
, c
x
.
8
H
p
,
e
2
,
,
,
,
l
3
,
8
.
3
H
,
1
C
C
,
9
4
f
p
y
r
r
o
l
e
)
,
5
.
0
(
1
4
H
H
,
,
J
H z
1
a
a
H
H
4
3
7
8
4
3
.
(
;
1
6
0
;
9
(
C
¼
N
2
S
)
.
a
l
c
f
o
:
H
C l N O ) :
2 5 2
C
N
s
H
o f
C
H
o
y
r
r
o
)
6
H
-
H
.
1
0
s
(
1
H
,
d
,
J
z
N
H
)
,
6
.
4
1
o
(
m
H
5
0
3
9
H
H
.
8
.
8
4
N
,
8
M
C
5
.
6
%
F
o
n
C
,
7
)
2
3
.
7
7
;
H
,
4
.
6
6
;
s
,
N
d
H
7
0
H
o
)
g
,
3
8
6
.
5
(
,
N
) ,
3
,
N
H
)
,
6
S
.
8
4
–
7
.
5
1
(
2
H
H
1
1
,
m
,
a
r
t
i
c
1
1
3
8
H
6
N
M
3
R
,
(
D
O
-
d
,
4
M
H
: δ
O
=
H
4
M
=
H
4
,
2 . 1 5 ( 3 H ,
h
y
r
n
s
)
M
R
(
D
M
O
- d6
0
,
9
,
1
0
0
C
)
Z
:
δ
=
2
0
.
8
4
6
7
6
Z
C
)
,
.
1
(
H
s
,
H
)
,
3
.
7
4
(
H
,
,
s
,
C
)
,
5
.
0
7
(
1
(
C
)
0
1
.
8
(
9
.
8
9
5
.
8
5
,
9
8
.
2
4
3
(
C ¼
)
5
1
2
5
.
0
0
4
(
,
,
1
1
o
2
7
.
2
9
a
,
,
c
3
3
3
3
s
,
C
r
H
l
,
o
o
,
p
.
y
r
r
o
l
1
,
e
)
,
.
2
1
(
1
H
=
,
4 JH
H
6
z
2
,
,
2
a
C
(
r
H
H
m
1
1
2
3
r
.
.
o
5
6
n
2
8
5
1
.
1
2
9
.
1
6
,
1
4
2
,
9
.
3
1
2
9
,
.
6
2
.
9
.
7
2
9
.
H
4
p
y
r
o
e
)
8
(
9
(
H
,
d
,
J
H
5
z
,
N
2
)
,
H
1
2
3
.
1
o
2
1
2
3
,
a
s ,
i
5
1
7
,
1
3
4
.
3
1
.
0
8
1
7
6
a
r
m
t
i
H
H
N
h
H
y
)
r
6
.
4
1
H
s
,
N
R
9
7
4
H
(
.
)
,
6
.
7
9
–
.
,
(
5
(
0
C
4
0
0
H
m
t
c
c
a
b
s
)
,
1
6
2
(
C
¼
N
)
.
1
3
d
H
5
9
1
g
e
n
0
1
1
1
s
)
,
C
C
-
N
M
D
M
S
O
-
d
1
0
)
:
δ
=
1
1
1
.
0
.
7
6
Z
2-(2-Chlorophenyl)-5-(4-chlorophenyl)-4-(5-(2-(2-
chlorophenyl)-5-(4-chlorophenyl)-1-p-tolyl-1H-imidazol-4-yl)-
1H-pyrrol-2-yl)-1-p-tolyl-1H-imidazole (7e).
(
C
)
,
2
.
8
2
.
.
(
H
) ,
3
4
9
8
,
2
2
9
8
.
3
7
,
,
s
C
¼
)
,
1
2
.
7
1
2
5
,
,
,
3.
8.
1.
8
9
6
2
9
7
,
,
,
3
Y
i
e
l
d
:
7
6
%
;
:
,
1
1
1
1
2
3
.
.
.
0
2
9
7
0
4
,
,
,
2
2
3
3
9
2
9
4
1
6
4
7
,
,
1
1
2
2
4
9
.
.
2
,
1
1
6
9
.
.
9
5
0
8
n
1
1
,
2
3
7
0
.
.
5
9
,
,
1
1
1
7
1
.
.
6
5
1
c
r
e
4
a
4
m
0
p
N
o
w
)
d
,
e
r
;
6
m
0
.
6
p
.
1
4
8 –
N
1
4
9
°
C
c
.
I
R
(
K
B
r
)
(
ῡ
,
c
m ꢀ
)
9
,
m
a
x
3
(
H
1
(
C
¼
)
.
C
a
l
d
.
f
o
r
(
C
H
C l N ) :
4 5
C
.
(
a
r
o
m
a
t
i
c
c
a
r
b
o
)
1
6
.
2
(
C
¼
N
)
4
8
3
3
J
o
u
r
n
a
l
o
f
H
e
t
e
r
o
c
y
c
l
i
c
C
h
e
m
i
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1
0
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1
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/
j
h
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t

2
7
7
8
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a
s
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u
d
i
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M
.
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h
a
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A
b
b
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j
a
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o
l
5
6
7
1
5-(4-Nitrophenyl)-4-(5-(5-(4-nitrophenyl)-2-phenyl-1-p-tolyl-
1H-imidazol-4-yl)-1H-pyrrol-2-yl)-2-phenyl-1-p-tolyl-1H-
imidazole (7i).
m
(
1
.
p
.
1
6
5
–
1
6
8
°
C
f
:
0
.
o
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r
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( ῡm
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c
2
5
9
8
;
%
(
H
.
N
H
)
,
1
9
6
;
M
0
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a
C
¼
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.
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a
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.
(
lN O ) :
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;
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1
1
2
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4
8
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2
5
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2
9
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1
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4
0
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1
2
9
7
2
8
3
1
.
3
Acknowledgment.
U
s
W
e
a
g
r
F
a
a
t
e
f
u
l
l
y
y
a
c
e
k
n
o
w
l
e
d
g
e
a
t
h
e
V
a
i
l
-
e
n
-
A
s
r
l
(
r
o
a
t
i
c
c
b
o
n
s
)
,
1
3
.
3
8
N
)
.
n
i
v
e
r
s
i
t
y
o
f
R
a
f
s
a
n
j
n
c
u
l
t
R
s
e
a
r
c
h
G
r
n
t
f
o
r
fi
n
a
c
i
a
2-(2-Chlorophenyl)-4-(5-(2-(2-chlorophenyl)-5-(4-
nitrophenyl)-1-p-tolyl-1H-imidazol-4-yl)-1H-pyrrol-2-yl)-5-(4-
nitrophenyl)-1-p-tolyl-1H-imidazole (7j).
u
p
p
o
r
t
.
Y
i
e
l
d
:
8
5
%
;
:
1
b
3
6
1
r
o
w
n
p
o
w
d
e
r
;
m
.
p
.
1
6
5
–
1
6
6
°
C
.
I
R
(
K
B
r
)
(
ῡ
,
c
m ꢀ
)
REFERENCES AND NOTES
m
a
x
4
8
1
6
.
.
H
3
1
4
7
(
N
H
)
,
1
6
5
0
;
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,
C
¼
N
.
D
)
.
C
a
l
F
4
.
c
d
.
f
o
r
(
C
H
C l N O ) :
2 7 4
C
N
s
e
H
,
,
,
,
,
4
8
3
3
[
1
]
,
]
S
a
c
h
i
n
,
S
.
K
.
;
R
a
m
e
s
h
,
R
.
P
.
;
A
t
u
l
S
,
K
.
I
n
t
J
C
u
r
r
A
d
v
R
e
s
1
5
)
;
%
H
,
3
H
7
.
9
1
1
6
3
%
.
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u
0
6
n
d
:
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6
8
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6
1
;
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3
.
7
3
;
2
2
0
0
1
6
8
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5
9
0
6
.
1
.
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,
9
,
5
.
N
3
C
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,
C
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1
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1
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)
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=
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2
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1
6
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y
7
r
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1
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r
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2
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2
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;
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4
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[
6
]
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]
]
R
o
m
a
n
,
G
d
e
;
C
,
P
h
K
R
h
M
.
e
a
;
a
i
l
e
y
,
2
.
B
e
V
b
I
J
0
L
.
0
i
G
,
e
o
0
r
.
1
S
w
;
5
c
,
4
V
,
i
l
a
3
0
h
2
0
C
,
c
N
P
a
k
i
s
,
J
.
Z
.
;
K
i
n
o
b
e
,
R
.
T
.
J
.
;
;
B
r
i
e
n
,
F
B
i
o
o
r
g
M
e
e
m
7
f
r
2
2
5
.
(
a
a
t
i
a
r
o
n
s
)
1
6
1
.
2
9
(
C
¼
N
)
.
[
[
7
8
B
a
b
i
z
h
a
y
v
,
C
.
G
m
A
2
6
,
7
8
,
2
l
3
4
3
.
3-(5-(4-Chlorophenyl)-2-phenyl-1-p-tolyl-1H-imidazol-4-yl)-
N
a
n
t
e
r
m
e
t
.
;
a
r
J
.
.
;
L
i
n
d
s
e
y
,
S
.
R
.
;
Y
o
u
n
g
,
M
.
1H-indole (10a).
Y
i
e
l
d
:
c
8
8
%
;
c
3
.
r
4
3
e
4
4
9
a
0
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%
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p
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)
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d
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;
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6
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p
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1
6
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–
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5
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8
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.
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f
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o
C
M
R
r
,
(
K
B
r
)
( ῡm
,
mꢀ
)
:
(
H
N
H
,
1
6
0
(
9
D
(
C
¼
N
)
.
[
9
]
]
a
]
2
]
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]
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]
7
]
G
u
t
a
,
V
.
;
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,
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s
i
i
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2
0
,
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a
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m
a
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3
0
2
2
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D
A
.
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;
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;
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SUPPORTING INFORMATION
1
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n
o
f
3-(2-(2-Chlorophenyl)-5-(4-nitrophenyl)-1-p-tolyl-1H-
imidazol-4-yl)-1H-indole (10c).
Y
i
e
l
d
:
8
8
%
;
c
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m
p
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