Thesis topic proposal
Tibor Kurtán
Domino cyclization reactions for the preparation of condensed chiral heterocycles


Institute: University of Debrecen
Doctoral School of Chemistry

Thesis supervisor: Tibor Kurtán
Location of studies (in Hungarian): Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary
Abbreviation of location of studies: E-423

Description of the research topic:

Stereoselective Knoevenagel-1,5-hydride shift-cyclization, Knoevenagel-hetero-Diels-Alder cascade reactions and alternative domino cyclization sequences of substituted furan, thiophene and other derivatives are to be carried out to prepare a small library of condensed chiral heterocycles for antiproliferative activity studies.
2H-chromene, furfural and thiophene-2-carbaldehyde derivatives are to be converted to precursors of domino cyclization reactions in short sequences, the reactions of which with acyclic and cyclic active methylene reagent are studied to afford different chiral scaffolds for bioactivity screening. The Knoevenagel-cylization sequences generates new chirality centers in the novel condensed chiral O- and O,N-heterocyclic scaffolds, which is expected to occur diastereoselectively. By using chiral non-racemic Lewis acids or organocatalysts, enantioselective transformations are planned to produce optically active target heterocycles. The enantiomeric excesses are to be analyzed by chiral HPLC coupled with electronic circular dichroism polarimeter and aided with ECD calculations. New domino cyclization mechanisms will be explored and novel condensed chiral heterocycles are to be synthesized for bioactivity screening. The stereoselectivity of the reactions is to be examined by spectroscopic methods including NMR methods and chiroptical measurements, X-ray diffraction and DFT calculations. Stereochemistry-bioactivity relationships are to be identified during the bioactivity screening of different diastereomers and enantiomers.

Required language skills: English
Number of students who can be accepted: 1

Deadline for application: 2022-01-15

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