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Sinteza 2-izobutil-3-metoksipirazina
ID Adamlje, Boštjan (Author), ID Grošelj, Uroš (Mentor) More about this mentor... This link opens in a new window

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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.

Language:Slovenian
Keywords:dišave, pirazin, ciklizacija
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-149532 This link opens in a new window
COBISS.SI-ID:164152067 This link opens in a new window
Publication date in RUL:07.09.2023
Views:492
Downloads:52
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Secondary language

Language:English
Title:Synthesis of 2-isobutyl-3-methoxypyrazine
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.

Keywords:fragrances, pyrazine, cyclization

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