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Mehanizam ciklizacionih reakcija za sintezu prekursora nekih fizioloških važnih jedinjenja

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2013
Disertacija.pdf (8.316Mb)
Author
Rvović, Marina
Mentor
Bugarčić, Zorica
Committee members
Vukićević, Rastko
Pavlović, Vladimir
Petrović, Biljana
Soldatović, Tanja
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Abstract
Supstituisana heterociklična kiseonikova jedinjenja, posebno ciklični etri terahidrofuransko- i terahidropiranskog tipa, privlače posebnu pažnju poslednjih godina, jer predstavljaju strukturne jedinice mnogih prirodnih proizvoda. Veliki broj ovih jedinjenja ispoljava citotoksičnu ili antibiotsku aktivnost. Zbog izuzetnog značaja ove klase molekula razvijen je veliki broj metoda za sintezu njihovih prekursora. Danas je dobro poznato da ciklofunckionalizacija nezasićenih alkohola pomoću elektrofilnih selenovih reagenasa predstavlja efikasnu metodu za sintezu ovog tipa kiseoničnih heterocikala. Prednosti ove metode se ogledaju u tome da se uvođenje heteroatoma u ciklični molekul, transformacija dobijenih proizvoda i uklanjanje funkcionalnih grupa u bočnom lancu dešavaju pri jednostavnim i blagim reakcionim uslovima. Prisustvo pažljivo odabranog katalizatora u ovim reakcijama može uticati na promenu raspodele reakcionih proizvoda i poboljšanje prinosa cikličnih etara. Iako su ove reakcije ...detaljno ispitivane, ostaje pitanje uloge katalizatora na kinetiku i mehanizam reakcija.

Substituted oxygen heterocycles, particularly cyclic ethers of tetrahydrofuran- and tetrahydropiran- types, have attracted special attention in recent years due to their occurrence as structural units of many marine natural products. A considerable fraction of these compounds exhibits notable cytotoxic and antibiotic activities. Due to the importance of this class of molecules, a number of methods have been developed for construction of its precursors. It is now well established that selenium-induced cyclofunctionalization of unsaturated alcohols represents a useful method for the synthesis of this type of oxygen heterocycles. This synthetic protocol has advantage that introduction of heteroatom, the manipulation of obtained product and the removal of the function in side chain is facilitated by simple and mild experimental conditions. The presence of properly selected catalyst can change distribution and improve the yields of obtained cyclic ether precursors. While the reaction has be...en thoroughly studied, questions remain pertaining to the role of catalyst on reaction kinetics and mechanistic pathway.

Faculty:
University of Kragujevac, Faculty of Science
Date:
10-06-2013
Projects:
  • Mechanistic studies of the reactions of transition metal ion complexes with biologically relevant molecules (RS-172011)
[ Google Scholar ]
URI
http://eteze.kg.ac.rs/application/showtheses?thesesId=359
http://nardus.mpn.gov.rs/handle/123456789/3598
https://fedorakg.kg.ac.rs/fedora/get/o:249/bdef:Content/download

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