diplomsko delo
Boštjan Adamlje (Author), Uroš Grošelj (Mentor)

Abstract

Iz N-Boc-L-levcina smo po dveh različnih sinteznih poteh pripravili 2-izobutil-3-metoksipirazin (IBMP). Po prvi smo pripravili amid z 2-aminoetanolom in alkoholni del oksidirali do aldehida. Le-tega smo pod kislimi pogoji ciklizirali do pirazinona, ki smo ga klorirali in z nukleofilno aromatsko substitucijo pretvorili do končnega metoksipirazina. Po drugi sintezni poti smo iz N-Boc-L-levcina pripravili L-levcinamid. Sledila je ciklizacija z glioksalom do pirazinona. Slednjega smo nato alkilirali z metil jodidom ali pa ga, kot v prvi sintezni poti, klorirali in z nukleofilno aromatsko substitucijo pretvorili do metoksipirazina.

Keywords

metoksipirazini;dišave;sintezne poti;ciklizacija;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [B. Adamlje]
UDC: 547.86.057(043.2)
COBISS: 164152067 Link will open in a new window
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Downloads: 6
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Other data

Secondary language: English
Secondary title: Synthesis of 2-isobutyl-3-methoxypyrazine
Secondary abstract: 2-Isobutyl-3-methoxypyrazine (IBMP) was prepared from N-Boc-L-leucine using two different synthesis pathways. Following the first synthesis pathway, an amide was synthesized with 2-aminoethanol and then the alcohol part was oxidized to an aldehyde. Afterwards, the aldehyde was cyclized under acidic conditions to pyrazinone, which was chlorinated and converted to the final methoxypyrazine by nucleophilic aromatic substitution. Using another synthesis pathway, L-leucinamide was prepared from N-Boc-L-leucine. This was followed by cyclization with glyoxal to pyrazinone. Pyrazinone was than alkylated with methyl iodide or, as in the first synthesis pathway, chlorinated and converted into methoxypyrazine by nucleophilic aromatic substitution.
Secondary keywords: fragrances;pyrazine;cyclization;Organska sinteza (kemija);Pirazin;Univerzitetna in visokošolska dela;
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: 34 f.
ID: 19908971