Synthesis and antimonoamine oxidase activity of 8-(N-methyl-N-2-propynyl)aminomethylquinolines


The starting 5-chloroand 5-bromo-8-methylquinolines (IIIb and d) were prepared by direct halogenation of 8-methylquinoline in concentrated sulfuric acid in the presence of silver sulfate [8]. 7-~11oro-8-methylquinoline (IIIc) was obtained by the Skraup reaction [9], and 5-fluoro-8-methylquinoline (IIIa) by the Baltz--Schiemann reaction [i0, ii] from 5-amino8-methylquinoline [12]. The nitrile (IIIe), esters (IIIf and g), and 8-bromomethyl derivatives (IVa, b, d-h) were obtained as described in [8] and [13]. 7-Chloro-8-bromomethylquinoline (IVc) and 5-nitro-8-bromomethylquinoline (IVh) were synthesized by hrominating (IIIc) and (IIIh) with N-bromosuccinimide. The nitro compound (IVh) was also obtained by nitrating 8-bromomethylquinoline as described in [14]. Reaction of quinolines (IVa-h) with N-methylpropargylamine (V) in methanol in the presence of potassium carbonate gave the propynylated derivatives (IIa-h); in the case of (IIc) and (IIh), (V) was used as the solvent. Alkylation of 8-(N-methyl)aminomethyl-5-quinolinecarboxylic acid (VI) [13] with propargyl bromide in the presence of alkali gave the acid (IIi)

DOI: 10.1007/BF00764174

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@article{Gracheva2004SynthesisAA, title={Synthesis and antimonoamine oxidase activity of 8-(N-methyl-N-2-propynyl)aminomethylquinolines}, author={I. N. Gracheva and I. R. Kovel'man and A. I. Tochilkin and I. V. Verevkina and D. I. Ioffina and V. Z. Gorkin}, journal={Pharmaceutical Chemistry Journal}, year={2004}, volume={17}, pages={625-629} }