4
-Substituted-
5
-phenyl-7-chloro-1, 2-dihydroimidazo [1, 2-α] quinolines (
6
ae
) (substituents at
4
-position were a : H, b : CH
3,
c
:
C6H5
,
d
: CN,
e
: N (CH
3)
2) and
5
-substituted-
6
-phenyl-
8
-chloro-2, 3-dihydro-1
H-pyrimido [1, 2-α] quinolines (7
ae
) (substituents at
5
-position were in accordance with the (
6
ae
)) were synthesized from 2-amino-
5
-chlorobenzophenone, and
KMnO4
oxidation of the above compounds in acetone were investigated.
The oxidation of (
6
ae
) caused dehydrogenation of the imidazo ring to give
4
-substituted-
5
-phenyl-7-chloro-imidazo [1, 2-α] quinolines (
8
ae
) in 3258% yields. On the other hand, the oxidation of (7ac) resulted in the selective oxidation of the methylene group at the 3-position of 2, 3-dihydro-1H-pyrimido ring to carbonyl group, and
5
-substituted-
6
-phenyl-
8
-chloro-1, 2-dihydro-3H-pyrimido [1, 2-α] quinoline-3-ones (
9
ac) were obtained in 3858% yields. The oxidations of the derivatives having CN or NMe
2 as substituents were difficult to proceed as compared with the cases of other substituted compounds.
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