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SINTEZA NEKATERIH 5,6-DISUBSTITUIRANIH 3-BENZOILAMINO-2H-PIRAN-2-ONOV IN NJIHOVA UPORABA V CIKLOADICIJAH Z MALEINANHIDRIDOM IN N-SUBSTITUIRANIM MALEIMIDOM
ID Ponikvar, Žiga (Author), ID Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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Abstract
V diplomskem delu so predstavljene enolončne sinteze 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov. Preučil sem različne metode, tudi uporabo mikrovalovnega obsevanja in sinteze pod visokim tlakom, primerne za izvajanje cikloadicij sintetiziranih 2H-piran-2-onov na maleinanhidrid in derivate maleimida. V eksperimentalnem delu sem želel ugotoviti, če so ti novejši pristopi primerni za sinteze izbranih biciklo[2.2.2]oktenskih aduktov, saj literaturni postopki vključujejo uporabo škodljivih topil, segrevanje pod refluksom in daljše reakcijske čase, kar vse predstavlja okolju neprijazne reakcijske pogoje. Sintetizirane produkte sem ovrednotil s TLC in spektroskopskimi metodami (1H NMR, IR, HRMS). Zaključil sem, da je enolončna metoda sinteze 2H-piran-2-onov uspešna z zadovoljivimi izkoristki, željeni cikloadukti pa nastanejo le z uporabo klasičnih pogojev segrevanja (refluks).

Language:Slovenian
Keywords:2H-piran-2-on, enolončna sinteza, cikloadicija, Diels–Alderjeva reakcija, mikrovalovna sinteza
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2018
PID:20.500.12556/RUL-102625 This link opens in a new window
COBISS.SI-ID:1537884867 This link opens in a new window
Publication date in RUL:05.09.2018
Views:1766
Downloads:603
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Secondary language

Language:English
Title:SYNTHESIS OF SOME 5,6-DISUBSTITUTED 3-BENZOYLAMINO-2H-PYRAN-2-ONES AND THEIR USE IN CYCLOADDITIONS WITH MALEIC ANHYDRIDE AND N-SUBSTITUTED MALEIMIDE
Abstract:
In this diploma I present one-pot synthetic approaches to 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones. Different methods were investigated, including microwave irradiation and high-pressure conditions, that can be used to prepare cycloadducts between 2H-pyran-2-ones and maleic anhydride, and maleimide derivatives respectively. In the experimental work I wanted to evaluate new approaches to the synthesis of the desired bicyclo[2.2.2]octene adducts, since the literature procedures use hazardous solvents, heating under reflux and longer reaction times which all represent environmentally detrimental reaction conditions. The synthesized products were characterized by TLC and spectroscopic methods (1H NMR, IR, HRMS). I concluded that the one-pot method of preparing 2H-pyran-2-ones results in satisfactory yiels, however, conventional approaches have to be used to successfully synthesize the desired cycloadducts.

Keywords:2H-pyran-2-one, one-pot synthesis, cycloaddition, Diels–Alder reaction, microwave synthesis

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