Chemistry Reference
In-Depth Information
Table 5.3 CDC reaction of tetrahydroisoquinolines with indoles by ball milling.
a
R
1
R
5
N
R
1
R
2
Ar
R
4
DDQ
+
N
R
3
N
R
4
Silica gel
R
2
Ar
R
5
ball milling
N
R
3
1
8
9
1a
: R
1
= R
2
= H, Ar = Ph
1b
: R
1
= R
2
= H, Ar = 4-MeOC
6
H
4
1d
: R
1
= R
2
= OMe, Ar = Ph
8a
: R
3
= H, R
4
= H, R
5
= H
8b
: R
3
= CH
3
, R
4
= H, R
5
= H
8c
: R
3
= H, R
4
= H, R
5
= OMe
8d
: R
3
= H, R
4
= H, R
5
= Br
8e
: R
3
= H, R
4
= CH
3
, R
5
= H
8f
: R
3
= H, R
4
= H, R
5
= NO
2
N
N
N
N
MeO
B
r
NH
NH
N
NH
9a
9b
9c
9d
77%, 30 min
(79%, overnight)
b
80%, 40 min
(44%, overnight)
b
70%, 20 min
(57%, overnight)
b
70%, 30 min
N
N
N
N
OMe
OMe
OMe
MeO
N
NH
NH
NH
9e
9f
9g
9h
75%, 40 min
(61%, overnight)
b
67%, 30 min
80%, 40 min
(71%, overnight)
b
72%, 40 min
(65%, overnight)
b
MeO
MeO
MeO
N
N
N
MeO
MeO
N
MeO
OMe
NH
N
MeO
NH
NH
9i
9j
9k
9l
70%, 40 min
65%, 50 min
67%, 45 min
63%, 50 min
MeO
MeO
MeO
N
N
MeO
MeO
N
MeO
O
2
N
O
NH
NH
9m + 9m′
(55% + 15%)
9n
70%, 40 min 61%, 50 min
a
Reactions were carried out with 1 (1.0 mmol), 8 (0.8 mmol), DDQ (1.0 mmol), silica gel (0.5 g)
and two copper balls (d
¼
8.0 mm) at 30 Hz, 20-50 min. Isolated yields based on 8.
b
The reaction time and isolated yields from ref. 1d.
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