含窒素芳香族複素環N-オキシドに対する酸クロリドおよびシアン化物の反応(第5報)1位および1位と4位に置換基のあるIsoquinoline 2-Oxideに対する芳香族カルボン酸クロリドおよびシアン化カリウムの反応について

抄録

Reaction with aroyl chloride and potassium cyanide was carried out with isoquinoline 2-oxide (Ix) with a substituent in 1-position or substituents in 1- and 4-positions. Ten kinds of Ix were used, including 1-phenyl-(Ia), 1-benzyl-(Ib), 1-methyl-(Ic), 1-ethyl-(Id), and 1-butyl-isoquinoline 2-oxide (Ie), isoquinolinecarbonitrile 2-oxide (If), 1, 4-diphenyl-(Ig) and 1-ethyl-2-phenyl-isoquinoline 2-oxide (Ih), 4-phenyl-1-isoquinolinecarbonitrile 2-oxide (Ii), and 1, 1'-diphenyl-4, 4'-biisoquinoline 2, 2'-dioxide (Ij), and results were as follows : 1) From 1-substituted isoquinoline 2-oxides, isoquinoline derivatives (II) with introduction of the aroyloxyl group into 4-position, accompanied with liberation of oxygen from the N→O group, were obtained. In some cases, 1, 4-dihydro-1-isoquinolinecarbonitrile derivatives (III) with introduction of CN group into 1-position and aroyloxy group into 4-position, accompanied with deoxygenation of N-O group, were formed. III is considered to be an intermediate in the formation of II. 2) III was formed from 1, 4-disubstituted isoquinoline 2-oxides. 3) A difference from the same reaction of quinoline derivatives was found in the absence of a derivative with introduction of the aroyloxy group into α-carbon when there is an alkyl group in 1-position and no formation of a derivative with introduction of the aroyloxy group into benzene portion of the isoquinoline ring when there is a phenyl group in 1-position.