イミダゾ [1, 2-α] キノリン類およびピリミド [1, 2-α] キノリン類の合成ならびにそれらの酸化反応 : o-アミノベンゾフェノン誘導体 (第11報)

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4-Substituted-5-phenyl-7-chloro-1, 2-dihydroimidazo [1, 2-α] quinolines (6ae) (substituents at 4-position were a : H, b : CH3, c : C6H5, d : CN, e : N (CH3) 2) and 5-substituted-6-phenyl-8-chloro-2, 3-dihydro-1H-pyrimido [1, 2-α] quinolines (7ae) (substituents at 5-position were in accordance with the (6ae)) were synthesized from 2-amino-5-chlorobenzophenone, and KMnO4 oxidation of the above compounds in acetone were investigated. The oxidation of (6ae) caused dehydrogenation of the imidazo ring to give 4-substituted-5-phenyl-7-chloro-imidazo [1, 2-α] quinolines (8ae) 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 (9ac) were obtained in 3858% yields. The oxidations of the derivatives having CN or NMe2 as substituents were difficult to proceed as compared with the cases of other substituted compounds.
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