Reaction of arylamines with aromatic aldehydes and β-ketoesters in the presence of bismuth nitrate or crystalline iodine as a catalyst afforded to alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3carboxy-lates. Antimicrobial activity of the obtained compounds was studied.The IR spectra of compounds Ia-Iy contained absorption bands of stretching vibrations of amino group (3220-3280 cm -1 ) and ester carbonyl moiety in the position 3 (1644-1670 cm -1 ). In the 1 H NMR spectra of compounds Ia-Iy there were the signals of aromatic ring (6.06-7.88 ppm), methylene group in the position 5 as AB system (2.42-2.97, 2.61-3.38 ppm, J 15.6 Hz ), the protons H 6 (4.93-6.12 ppm) and H 2 (5.50-6.40 ppm) as well as of NH group (9.89-10.69 ppm).
Mass spectrum ofIa contained the molecular ion peak [M] + with m/z 460 and the fragment ion peaks with m/z 383 [M -Ph] + , 368 [M -PhNH] + , 180 [PhNCH 2 Ph] + , 77 [Ph] + that confirmed the suggested structure. Mass spectra of other compounds Ib-Iy were similar.The assumed mechanism of this reaction is analogous to that described previously in the literature [2,10,12,13,17]. The aromatic amine reacts with βketoester and an aromatic aldehyde in the presence of a catalyst to form enamine A and imine B, respectively.
Reaction of 4-aryl-2-hydroxy-4-oxo-2-butenoic acid N-hetarylamides with copper, zinc, and cadmium dichlorides led to the formation of bis[3-aryl-1-(N-hetaryl)carboxamido-1,3-propanedionato]copper, -zinc, and -cadmium, respectively. Compounds with high antimicrobial activity were found among these products.
3890091-150X/08/4207-0389
A series of 17 new substituted amides and hydrazides of N-acyl-5-bromanthranilic acids were synthesized. The antimicrobial activity of these compounds with respect to St. aureus and E. coli was evaluated. It was found that of N-chloracetyl-5-bromanthranlic acid methylamide and hydrazide significantly suppressed the growth of test microbes, with a minimum inhibitory concentration of 15.6 mg/ml against St. aureus and 15.6 -31.5 mg/ml against E. coli. The other tested compounds were significantly less active. 483 0091-150X/07/4109-0483
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