On the reaction of acridine with ketones

Abstract

Reaction of acridine (I) with various ketones (II), in the presence of sodium methoxide at ordinary temperature, was examined. Ketones used were acetophenone, propiophenone, butyrophenone, valerophenone, isobutyrophenone, isovalerophenone, acetone, diethyl ketone, diisobutyl ketone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, cyclohexinone, and cyclopentanone. From the results of this reaction, following points were clarified. 1) When the reaction is effected, the carbonatom of the methyl or methylene group adjacent to the carbonyl group in the ketone is bonded to 9-position of I to form the acridanyl derivative (III). 2) Although the examples are small, the reaction seemed difficult when the alkyl group in the ketone possessed a branched chain in the α- and or β-position. 3) The carbon bonded to the carbonyl group in the ethyl or propyl group seemed to have greater reactivity than the carbon in the methyl group bonded to the carbonyl. The actidanyl derivatives (III) are derived to the corresponding acridine derivatives (IV) by oxidation with chloranil. However, in the case of 2-(9-acridanyl)cyclopentanone (IIIn), 9-acridine-valeric acid (Vn), considered to be formed by the hydrolysis of 2-(9-acridinyl)-1-cyclopentanone (IV) during the treatment, was obtained. Hydrolysis of the acridine derivatives (IV) with sodium hydroxide afforded 9-alkylacridine (V) except in the case of 2-(9-acridinyl)-1-cyclohexanone (IVm) which formed 9-acridine-caproic acid (Vm).