I. N. Gracheva

Bromination of quinoline derivatives with N-bromosuccinimide. Isomeric composition of the bromination products by PMR and GLC

The bromination of quinoline and substituted quinolines with N-bromosuccinimide in concentrated H2SO4 takes place exclusively in the homocyclic part. Bromo-substituted quinolines can be obtained by this method. The bromination products were identified by PMR spectroscopy. The differences among the mono-, di-, and trisubstituted (in the benzene ring) compounds were established on the basis of the type of spectrum of the protons of the homocyclic part of the molecule. The compositions of the reaction mixtures were studied by GLC.

Synthesis and bromination of 8-methylquinoline-5-carboxylic acid

Abstract8-Methylquinoline-5-carboxylic acid was obtained by the Skraup reaction from 3-amino-p-toluic acid or by hydrolysis of 5-cyano-8-methylquinoline. The latter was synthesized by the Rosenmund-von Braun reaction from 5-bromo-8-methylquinoline, which was obtained by bromination of 8-methylquinoline in the presence of silver sulfate. Bromination in the side chain of 8-methylquinoline-5-carboxylic acid and its nitrile was studied.

Synthesis of N-(8-methoxy-5-quinolylsulfonyl)aziridine and its reactions with secondary amines. PMR spectra and structures of the derivatives obtained

A method for the synthesis of a new fluorescent derivative of ethyleneimine, viz., N-(8-methoxy-5-quinolylsulfonyl)-aziridine, starting from 8-methoxyquinoline-5-sulfonyl chloride was developed. The quinolylsulfonylaziridine reacts smoothly with secondary aliphatic amines to give 8-methoxy-5-[N-(2-N-dialkylethylamino)] quinolinesulfonamides. In a study of the PMR spectra of these compounds it was established that significant deshielding of the 4-H proton (0.8 ppm) and a substantial increase (by 0.8 ppm) in 3J(6,7) are characteristic signs of the introduction of aziridinylsulfonyl or N-(2-N-dialkylamino)sulfonamido substituents into the 5 position of 8-methoxyquinoline.

Synthesis and properties of a fluorescent derivative of quinoline —N-[N-(6-aminohexyl)-5-dimethylamino-1-naphthylsulfonamido]-8-(N-methyl-N-2-propynyl)aminomethylquinoline-5-carboxamide

The synthesis of quinoline derivatives that contain a fluorogenic grouping by condensation of 8-(N-methyl-N-carbobenzoxy)aminomethylquinoline-5-carboxylic acid azide with N-(6-aminohexyl)-5-dimethylaminonaphthalenesulfonamide is described. The resulting carboxamide was subjected to hydrogenolysis, and subsequent reaction with propargyl bromide led to the title compound.

Synthesis of N-2-propynyl-ω-aminoalkyl-8-quinolinesulfonamides

N-2 Propynyl-ω-aminoalkyl-substituted 8-quinolinesulfonamides, which are potential inhibitors of monoaminooxidase, were synthesized by alkylation of ω-aminoalkyl-8-quinolinesulfonamides with propargyl halides or by aminolysis of ω-chloroalkyl-8-quinolinesulfonamides with N-methylpropargylamine.