The reaction of heteroaromatic n-oxide with acid chloride and cyanide. I. On the reaction of 2-substituted and 2,3-disubstituted quinoline 1-oxides with aroyl chloride and potassium cyanide (author's transl)

Abstract

Reaction of quinoline 1-oxides, possessing alkyl or phenyl group in 2 or 2 and 3 positions, with benzoyl chloride and potassium cyanide was carried out. Substituents in the quinoline 1-oxides used were the following 13 ; 2, 4-tetramethylene (Ia), 2, 3-trimethylene (Ib), 2, 3-dimethyl (Ic), 2-ethyl-3-methyl (Id), 2-methyl (Ie), 2-propyl (If), 2-isobutyl (Ig), 2-isopropyl (Ih), 2-phenyl (Ii), 3-methyl-2-phenyl (Ij), 2-phenyl-3-propyl (Ik), 2, 3-diphenyl (II), and 3-bromo-2-phenyl (Im), and the results may be summarized as follows : 1) When the reaction is carried out in aqueous solution, tetrahydroquinoline derivatives with introduction of -OH (-OCH3 when reacted in methanol) into 2-position, [chemical formula]into 3-position, and -CN into 4-position are formed, accompanied by deoxygenation of N→O group. Such derivatives are not formed from Ie, Ii, and Im. 2) When there is an alkyl group in 2-position, derivatives with [chemical formula] introduced into the carbon atom α to the alkyl group are also formed, accompanied by deoxygenation of N→O group. 3) When the original compound contains a phenyl group in 2-position, derivatives with [chemical formula] introduced into 6- or 8-position are also formed, accompanied with deoxygenation of N→O group. When the reaction is carried out in methanol, -OCH3 group is introduced into 6-position in the case of Ib and Ii. This reaction was attempted with 2-furoyl chloride, p-anisoyl chloride, nicotinoyl chloride, and p-nitrobenzoyl chloride as the acid chloride. There was no especially notable effect of the electronic effect of electron-donating or -attracting group in these acid chlorides on the reaction results.