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3-Acilamino-2H-piran-2-oni in njihovi derivati kot dieni za [4+2] cikoadicije z različnimi cikličnimi elektronsko siromašnimi alkeni
ID Kušar, Dominik (Author), ID Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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Abstract
V diplomskem delu sem z enolončno sintezno metodo uspešno sintetiziral dva različno substituirana 3-benzoilamino-2H-piran-2-ona. V nadaljevanju sem, dvakrat uspešno in enkrat neuspešno, na izbranih 3-benzoilamino-2H-piran-2-onih odstranil benzoilaminsko skupino. Odščitene derivate sem nato reagiral z enojnim in dvojnim kislinskim kloridom, pri čemer sem pri slednjem uspešno izoliral sistem, kjer sta povezana dva 2H-piran-2-onska obroča. Tri izbrane 3-benzoilamino-2H-piran-2-onske derivate sem reagiral z maleinanhidridom in pri tem izoliral serijo biciklo[2.2.2]oktenskih aduktov. Na izbranem biciklo[2.2.2]oktenskem aduktu sem s hidrazin hidratom poskušal pretvoriti sukcinanhidridni obroč v N-aminosukcinimidni obroč, vendar neuspešno. V zadnjem sklopu reakcij sem izvedel reakcijo med dvema izbranima biciklo[2.2.2]oktenskima aduktoma in dvema različnima hidrazidoma.

Language:Slovenian
Keywords:enolončna sinteza, Diels–Alderjeva reakcija, 2H-piran-2-on, biciklo[2.2.2]oktenski adukt, hidrazid, hidrazin hidrat, maleinanhidrid
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2023
PID:20.500.12556/RUL-148944 This link opens in a new window
COBISS.SI-ID:165224195 This link opens in a new window
Publication date in RUL:01.09.2023
Views:1223
Downloads:76
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Secondary language

Language:English
Title:3-Acylamino-2H-pyran-2-ones and their derivatives as dienes for [4+2] cycloadditions with various cyclic electron-deficient alkenes
Abstract:
In this diploma, I successfully synthesized two differently substituted 3-benzoylamino-2H-pyran-2-ones by one-pot synthesis method. Next, I removed the benzoylamino group on selected 3-benzoylamino-2H-pyran-2-ones, twice successfully and once unsuccessfully. Then I introduced two new protecting groups on the 3-amino end of the molecule, one with an acid chloride and the other with a double acid chloride. In the latter I successfully isolated a system where two 2H-pyran-2-ones are connected. I reacted three selected 3-benzoylamino-2H-pyran-2-one derivatives with maleic anhydride and isolated a series of bicyclo[2.2.2]octene adducts. On the selected bicyclo[2.2.2]octene adducts I tried to convert the succinic anhydride ring to the N-aminosuccinimide ring with hydrazine hydrate, but without success. In the last set I performed reactions between two selected bicyclo[2.2.2]octene adducts and two different hydrazides.

Keywords:one-pot synthesis, Diels–Alder reaction, 2H-pyran-2-one, bicyclo[2.2.2]octene adduct, hydrazide, hydrazine hydrate, maleic anhydride

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