magistrsko delo
Simon Kebelj (Avtor), Krištof Kranjc (Mentor), Romana Cerc Korošec (Član komisije za zagovor), Franc Požgan (Član komisije za zagovor)

Povzetek

V okviru magistrske naloge sem pripravil serijo novih 3-acilamino-2H-piran-2-onom z uvedbo nove zaščitne skupine na 3-aminsko skupino z izbranimi kislinskimi kloridi. Te sem nadalje pod termičnimi pogoji reagiral z maleinanhidridom z namenom priprave novih biciklo[2.2.2]oktenskih sistemov s pripojenima sukcinanhidridnima fragmentoma (produkti dvojne Diels–Alderjeve cikloadicije), vendar so v nekaterih primerih namesto bicikličnih dvojnih aduktov nastali termodinamsko stabilnejši aromatski produkti (derivati izobenzofurana). Nekatere izmed pripravljenih biciklo[2.2.2]oktenskih aduktov sem uporabil pri nadaljnjih reakcijah derivatizacije z izbranimi dušikovimi nukleofili (hidrazinom, n-butilaminom ter 3-pikolil aminom). Serijo izbranih 3-acilamino-2H-piran-2-onov sem preizkusil tudi pri reakciji z etil vinil etrom v prisotnosti DABCO pod pogoji mikrovalovnega obsevanja, pri čemer sem s prilagajanjem reakcijskih pogojev (temperatura, moč segrevanja, reakcijski čas) uspel pripraviti nekaj novih benzenskih derivatov. Z namenom priprave oksabiciklo[2.2.2]oktenskih aduktov, ki jih ni mogoče pripraviti po konvencionalni poti s segrevanjem reakcijske zmesi zaradi termične neobstojnosti tovrstnih struktur, sem izbrane 2H-piran-2-one reagiral z različnimi dienofili pod pogoji visokega tlaka, vendar sem bil uspešen le v dveh primerih. Pod pogoji visokega tlaka sem med drugim uspešno pripravil dvojni CO2-premosten adukt, ki vsebuje dve oksabiciklo[2.2.2]oktenski enoti, povezani med seboj prek izoftalamidnega mostička.

Ključne besede

2H-piran-2-on;Diels-Alderjeva cikloadicija;benzenovi derivati;biciklo[2.2.2]okten;visokotlačna sinteza;mikrovalovna sinteza;magistrska dela;

Podatki

Jezik: Slovenski jezik
Leto izida:
Tipologija: 2.09 - Magistrsko delo
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
Založnik: [S. Kebelj]
UDK: 547.81(043.2)
COBISS: 173367043 Povezava se bo odprla v novem oknu
Št. ogledov: 80
Št. prenosov: 27
Ocena: 0 (0 glasov)
Metapodatki: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Ostali podatki

Sekundarni jezik: Angleški jezik
Sekundarni naslov: Preparation of substituted 2H-pyran-2-ones, followed by conversions to bicyclic adducts and benzene derivatives via Diels-Alder reactions
Sekundarni povzetek: As part of this master's thesis a series of novel 3-acylamino-2H-pyran-2-ones were prepared by introduction of a new protecting group on the 3-amine group with selected acid chlorides. Those were further reacted under thermal conditions with maleic anhydride in order to prepare new bicyclo[2.2.2]octene systems with two attached succinic anhydride fragments (products of double Diels–Alder cycloaddition), however in some cases thermodynamically more stable aromatic products (isobenzofuran derivatives) were formed instead of otherwise kinetically favoured bicyclic double adducts. Some of the prepared bicyclo[2.2.2]octene adducts were used in further derivatization reactions with selected nitrogen nucleophiles (hydrazine, n-butylamine and 3-picolyl amine). A series of selected 3-acylamino-2H-pyran-2-ones were also tested under microwave irradiation conditions in the presence of ethyl vinyl ether and DABCO. By adjusting the reaction conditions (temperature, heating power, duration of reaction time) some novel benzene derivatives were successfully prepared. In order to prepare oxabicyclo[2.2.2]octene adducts, which cannot be prepared by the conventional route by heating the reaction mixture due to the thermal instability of structures of this type, reactions with selected 2H-pyran-2-ones with various dienophiles were carried out under high-pressure conditions. However, I was only successful in two cases. In one case a double CO2-bridged adduct containing two oxabicyclo[2.2.2]octene units connected via an isophthalamide bridge was successfuly synthesized.
Sekundarne ključne besede: 2H-pyran-2-one;Diels-Alder sycloaddition;benzene derivative;bicyclo[2.2.2]octene;high-pressure synthesis;microwave synthesis;Pirani;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
Vrsta dela (COBISS): Magistrsko delo/naloga
Študijski program: 1000375
Konec prepovedi (OpenAIRE): 1970-01-01
Komentar na gradivo: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Strani: 139 str.
ID: 20041927