Marrugo G. Chalcones, 2 pyrazolines, 2,3 dihydro-1H-1,5 benzodiazepines, containing 8 hydroxyquinoline fragment

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0409U000328

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

16-01-2009

Specialized Academic Board

Д 64.051.14

V.N. Karazin Kharkiv National University

Essay

Objects of investigation:. ?,?-unsaturated ketones, containing 5 (8 hydroxyquinoline) fragment, 2 pyrazolines and 2,3-dihydro-1Н-1,5-benzodiazepines. The aim: the synthesis and investigation of structure, physical-chemical, spectral and che-lating properties of ?,?-unsaturated ketones, containing 5 (8 hydroxyquinoline) fragment and obtained on their base 2 pyrazolines and 2,3-dihydro-1Н-1,5-benzodiazepines. The methods: organic synthesis, NMR1H, IR, UV-VIS spectroscopy of absorbance and emission, element analysis, PASS (Prediction of Activity Spectra for Substance). Scientific novelty: It is shown, that chalcones, based on 5 formyl and 5 acetylderivatives of 8 hydroxyquinoline, are obtained with good yields under alkali catalysis and have major s cis-trans-geometry of propenone fragment with its anti-orientation toward quinoline fragment. It is discovered, that the most basic center of these molecules is nitrogen atom of heterocycle, estimated constants its protona-tion and deprotonation of HO-group.It is shown, that the bro-mination of enone system may be done after the process of bro-mination of heterocycle is complete. It is estimated, that 5 (8 hydroxyquinoline) fragment causes considerable bato-chrome and batophlore effect, when it is introduced in position 3 of 2 pyrazoline. First the ability of 5 (8 hydroxyquinoline) derivatives of 2,3 dihydro-1H-1,5 benzodiazepine obtaining is shown. It is shown, that their synthesis is complicated by side process of contraction of seven-membered ring to five-membered. Application: it was optimized of synthesis conditions of 5 formyl-8 hydroxyquinoline by Reimer-Timan reaction. It was proposed of new group of ?,?-unsaturated ketones, containing 5 (8 hydroxyquinoline) fragment, with chelating properties and revealed opportunities of their application in 2 pyrazolines and 2,3-dihydro-1Н-1,5-benzodiazepines synthesis, investigated their complexing and chromophoric properties. Computer esti-mation of biological activity of compounds obtained was done using PASS.

Files

Similar theses