Simetriski aizvietotu un hirālu 1,4-dihidropiridīnu sintēze un elektroķīmiskā izpēte
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Latvijas Universitāte
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Abstract
Darbā izstrādātas divas metodes jaunu 1,4-dihidropiridīnu rindu iegūšanai. Elektroķīmiski reducējot piridīnija perhlorātu alkilhalogenīdu klātbūtnē, iegūti heterociklā pilnīgi aizvietoti 1,4-dihidropiridīni ar atšķirīgiem aizvietotājiem pie C-4 atoma. Iegūta jauna nesimetriski aizvietotu 1,4-dihidropiridīnu rinda, izmantojot modificēto Hanča sintēzi; izpētīts iegūto savienojumu elektroķīmiskās oksidēšanas mehānisms. Pat vāji bāziskās vidēs oksidēšanas produktā – piridīnija sālī elektronakceptorie aizvietotāji iekšmolekulārās ciklizācijas rezultātā veido laktona ciklu.
Two methods have been developed for obtaining new derivatives of 1,4-dihydropyridines. Fully substituted 1,4-dihydropyridines bringing two different substituents at C-4 were obtained by electrochemical reduction of a pyridinium salt in the presence of alkyl halides. The new row of unsymmetrically substituted 1,4-dihydropyridines was synthesized using modified Hantzsch method; the mechanism of their electrochemical oxidation has been investigated. Electron withdrawing groups in the pyridinium salt – the product of the oxydation, undergo intramolecular cyclization producing the lactone cycle even in the weakly basic media.
Two methods have been developed for obtaining new derivatives of 1,4-dihydropyridines. Fully substituted 1,4-dihydropyridines bringing two different substituents at C-4 were obtained by electrochemical reduction of a pyridinium salt in the presence of alkyl halides. The new row of unsymmetrically substituted 1,4-dihydropyridines was synthesized using modified Hantzsch method; the mechanism of their electrochemical oxidation has been investigated. Electron withdrawing groups in the pyridinium salt – the product of the oxydation, undergo intramolecular cyclization producing the lactone cycle even in the weakly basic media.