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Acetofenonele în sinteza compuşilor heterociclici


Author: Serghei Pogrebnoi
Degree:doctor of chemistry
Speciality: 02.00.03 - Organic chemistry
Year:2006
Scientific adviser: Fliur Macaev
doctor habilitat, professor, Institute of Chemistry, Academy of Sciences of Moldova
Institution:
Scientific council:

Status

The thesis was presented on the 10 February, 2006
Approved by NCAA on the 27 April, 2006

Abstract

Adobe PDF document0.36 Mb / in romanian
Adobe PDF document0.41 Mb / in russian

Thesis

CZU 547.572+547.78+547.792

Adobe PDF document 0.77 Mb / in russian
91 pages


Keywords

Acetophenones, synthesis, heterocyclic compounds, 1,3-dioxolanes, pyrazolines, chalcones, oxoindoles, 2-mercapto-5-phenyl-1,3,4-oxadiazoles, 2-amino-1-arylidenaminoimidazoles, 1-arylidenaminoimidazo[1,2-α]imidazoles

Summary

This monograph presents the synthesis of new heterocyclic compounds possessed a potential biological activity. Starting from acetophenones, benzoic and salicylic acids, syntheses of five-member heterocycles, contained 1,2,4-triazol, oxadiazol, pyrazol, thiazol, and 1,3-dioxolan fragments, were performed. Initial acetophenones were transformed to corresponding phenacyl bromides, 1,3 –dioxolanes, 2–bromomethyl-2-phenyl-1,3-dioxolanes, and chalkones. It was shown that ketalization of phenacyl bromides gives higher yields of 2–bromomethyl-2-phenyl-1,3-dioxolanes then bromination of 2–methyl-2-phenyl-1,3-dioxolanes.

Reaction of phenacyl bromides with benzalguanidine was investigated, and it was shown that the nature of reaction products depends on the ratio of initial reagent: when the ration is equimolar, derivatives of 1,2-diamino-4-phenylimidazole were obtained; using of two equivalents of phenacyl bromide leads to derivatives of imidazo-[1,2α]-imidazole. A new preparative procedure for the synthesis of active compound of system fungicide “TILT” was developed.

At the first time it was obtained that using one-pot reaction it is possible to transform available chalkones to very stable pyrazolines with a high yield. It was shown that derivatives of acetophenones with pyrazolin and oxindol fragments possess an antidepression activity. Based on hydrazides of benzoic and salicylic acids, the synthesis of 5-aryl-2-thio-1,3,4-oxadiazoles was performed. A number of synthesized compounds possess a high antituberculosis activity.