diplomsko delo
Jakob Muhič (Author), Bogdan Štefane (Mentor)

Abstract

Oksazoloni so zaradi svoje reaktivnosti odlični izhodni substrati za odkrivanje sinteznih poti za nove heterociklične in aminokislinske produkte. Iz hipurne kisline in 2-bromobenzaldehida, v prisotnosti acetanhidrida in kalijevega acetata, sem po Erlenmeyer azlakton postopku sintetiziral 4-(2-bromobenziliden)-2-feniloksazolon. Produkt sem z dodatkom trietilamina v metanolu pretvoril do metil 2-N-benzamido-3-(2-bromofenil)akrilata. Za zaključek sem izvedel še hidrogeniranje akrilata, raztopljenega v metanolu, s 10 mol% katalizatorja tris(trifenilfosfin)rutenijev (II) diklorid in dobil končni produkt metil 2-N-benzamido-3-(2-bromofenil)propanoat. Ugotovil sem, da je celotna sintezna pot zadosti ponovljiva, ter ima dobre izkoristke na vseh sinteznih korakih.

Keywords

organska sinteza;heterociklične spojine;heterocikli;oksazoloni;4-benziliden-2-feniloksazolon;oksazolonski obroč;hidrogeniranje;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [J. Muhič]
UDC: 547.787(043.2)
COBISS: 84650755 Link will open in a new window
Views: 292
Downloads: 57
Average score: 0 (0 votes)
Metadata: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Other data

Secondary language: English
Secondary title: Synthesis and transformations of 4-benzylidene-2-phenyloxazolones
Secondary abstract: Due to their reactivity, oxazolones make excellent starting substrates in diversity oriented synthesis for discovering new synthetic pathways for the formation of amino acid and heterocyclic products. Using the Erlenmeyer azlactone synthesis, I synthesized 4-(2-bromobenzylidene)-2-phenyloxazolone, using hippuric acid and 2-bromobenzaldehyde as starting substrates in the presence of acetic anhydride and potassium acetate. I converted the product to methyl 2-N-benzamido-3-(2-bromophenyl) acrylate by adding triethylamine in methanol. I finished the process with the hydrogenation of the obtained acrylate in methanol with 10 mol% of the catalyst tris(triphenylphosphine)ruthenium(II) dichloride. The final product was methyl 2-N-benzamido-3-(2-bromophenyl) propanoate. I found the method of synthesis to be sufficiently repeatable, and has good efficiencies at all steps.
Secondary keywords: oxazolone;heterocycle;hydrogenation;
Type (COBISS): Bachelor thesis/paper
Study programme: 1000373
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages: 23 str.
ID: 13381020