Badania nad syntezą C-azanukleozydów z wykorzystaniem N-tlenków 5,5-bis(hydroksymetylo)-1-piroliny

Mariola Koszytkowska-Stawińska

Abstract

The possibility of using of 5,5-bis(hydroxymethyI)-l-pyrroline N-oxides in the synthesis of C-azanucleosides was investigated. In those support the 1,3-dipolar cycloaddition reaction of 1-aza-7,14-dioxadispiro[4.5.2.51pentadec-l-ene to N-phenymaleimide was applied. Next the oxidation with m-chloroperbenzoic acid and the reduction with hydrogen in the presence of Raney-nickel of the product was carried out; the acyclic product was obtained in the oxidation reaction while the catalytic hydrogenation gave iso-Showdomycine azaanalogue. Next the addition reaction of arylmagnesium compounds to l-aza-7,14-dioxadispiro[4.5.2.5jpentadec-l-ene was applied. The products were allowed to react with acid chlorides. The appropriate derivatives of 3-acyloxy-l-pyrroline were the products, reduction of which with sodium borohydride was carried out. The mixture of cis- and trans-2-aryl-3-hydroxy-5,5-bis(hydroxymethy)-pyrrolidine derivatives was obtained.
Diploma typeDoctor of Philosophy
Author Mariola Koszytkowska-Stawińska (FC / DOC)
Mariola Koszytkowska-Stawińska,,
- Department Of Organic Chemistry
Title in PolishBadania nad syntezą C-azanukleozydów z wykorzystaniem N-tlenków 5,5-bis(hydroksymetylo)-1-piroliny
Languagepl polski
Certifying UnitFaculty of Chemistry (FC)
Disciplinechemistry / (chemical sciences domain) / (physical sciences)
Defense Date06-04-2001
Supervisor Daniela Buza (FC)
Daniela Buza,,
- Faculty of Chemistry

Pages174
Keywords in Polishchemia leków, chemia organiczna, synteza organiczna, chemia farmaceutyczna, prace doktorskie
Abstract in EnglishThe possibility of using of 5,5-bis(hydroxymethyI)-l-pyrroline N-oxides in the synthesis of C-azanucleosides was investigated. In those support the 1,3-dipolar cycloaddition reaction of 1-aza-7,14-dioxadispiro[4.5.2.51pentadec-l-ene to N-phenymaleimide was applied. Next the oxidation with m-chloroperbenzoic acid and the reduction with hydrogen in the presence of Raney-nickel of the product was carried out; the acyclic product was obtained in the oxidation reaction while the catalytic hydrogenation gave iso-Showdomycine azaanalogue. Next the addition reaction of arylmagnesium compounds to l-aza-7,14-dioxadispiro[4.5.2.5jpentadec-l-ene was applied. The products were allowed to react with acid chlorides. The appropriate derivatives of 3-acyloxy-l-pyrroline were the products, reduction of which with sodium borohydride was carried out. The mixture of cis- and trans-2-aryl-3-hydroxy-5,5-bis(hydroxymethy)-pyrrolidine derivatives was obtained.
Thesis file
Koszytkowska_Stawinska_Mariola_badania.pdf 6.2 MB
Citation count*4 (2015-07-23)

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