Atropizomēru sintēze un to fizikāli ķīmisko īpašību izpēte simetriski un nesimetriski aizvietotu 1,4-dihidropiridīnu rindā
Date
2016
Authors
Lielpētere, Anna
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Journal ISSN
Volume Title
Publisher
Latvijas Universitāte
Abstract
Modificētā Hanča sintēzē ieguva simetriski un nesimetriski aizvietotus 1,4-dihidropiridīnu atropizomērus ar 2-(benzoksi)naft-1-il)-, 2-(naft-2-ilmetoksi)naft-1-il)- un citām stēriski lielām grupām heterocikla 4-vietā. Iegūtajiem savienojumiem ir apgrūtināta C(4)-C(1’) saites rotācija, un tās enerģijas barjeras novērtēšanai izmantoja 1D un 2D KMR spektroskopiju, mainot šķīdinātājus un uzņemšanas temperatūru, kā arī rentgenstruktūranalīzi un šķidrumu hromatogrāfiju ar hirālu kolonnu. 1,4-Dihidropiridīniem noteikti arī elektroķīmiskās oksidēšanās potenciāli.
In modified Hantzsch synthesis, symmetrically and unsymmetrically substituted 1,4-dihydropyridine atropisomers with (2-(benzyloxy)naphthalen-1-yl)-, 2-(naphthalen-2-ylmethoxy)naphthalen-1-yl- and other bulky groups in the 4-position were obtained. Rotation around C(4)-C(1’) bond in the synthesized compounds is hindered, and rotational energy barriers were estimated using 1D and 2D NMR spectroscopy in different solvents and temperatures as well as X-ray analysis and LC with a chiral column. Oxidation potentials of the 1,4-dihydropyridines were also determined.
In modified Hantzsch synthesis, symmetrically and unsymmetrically substituted 1,4-dihydropyridine atropisomers with (2-(benzyloxy)naphthalen-1-yl)-, 2-(naphthalen-2-ylmethoxy)naphthalen-1-yl- and other bulky groups in the 4-position were obtained. Rotation around C(4)-C(1’) bond in the synthesized compounds is hindered, and rotational energy barriers were estimated using 1D and 2D NMR spectroscopy in different solvents and temperatures as well as X-ray analysis and LC with a chiral column. Oxidation potentials of the 1,4-dihydropyridines were also determined.
Description
Keywords
Ķīmija , atropizomēri , 1,4-dihidropiridīni , mainīgas temperatūras KMR spektroskopija , elektroķīmiskā oksidēšana , rentgenstruktūranalīze