Elektrokemijske in termične pretvorbe derivatov dihidropirazinov ter derivatov indolov z uporabo grafitnih elektrod in aktivnega oglja

Užmah, Blaž (author), Kranjc, Krištof (mentor)

V magistrskem delu so predstavljene elektrokemijske pretvorbe derivatov indolov ter derivatov dihidropirazinov, izvedene z uporabo grafitnih elektrod, in termične pretvorbe derivatov dihidropirazinov v zaprtih ACE cevkah z uporabo aktivnega oglja kot katalizatorja. Pri elektrokemijskih pretvorbah sem se odločil, da iz komercialno dostopnih komponent sestavim in preučim za uporabnika preprost sistem za elektrokemijske sinteze. Tekom sintez sem uporabljal grafitne elektrode; želel sem namreč preveriti njihovo učinkovitost pri sintezah glede na dražje platinaste elektrode. Pri termičnih pretvorbah sem hotel preveriti, ali je možno reakcijo aromatizacije 5,6-difenil-2,3-dihidropirazina v 2,3-difenilpirazin posplošiti na ostale derivate dihidropirazinov, ki sem jih sintetiziral sam. Reakcije sem spremljal s TLC in končne produkte ovrednotil s spektroskopskimi metodami – 1H NMR ter HRMS. Ugotovil sem, da so grafitne elektrode pri pretvorbah derivatov dihidropirazinov relativno uspešne, pri indolih reakcije potekajo le v sledovih. Pri reakcijah termične aromatizacije sem ugotovil, da se lahko takšne reakcije aromatizacije posploši na različne derivate dihidropirazinov.

• Language: Slovenian
• Keywords: elektrokemijska sinteza, dehidrogeniranje, indoli, derivati dihidropirazinov, aktivno oglje
• Work type: Master's thesis/paper
• Typology: 2.09 - Master's Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2023
• PID: 20.500.12556/RUL-151872
• COBISS.SI-ID: 174359299
• Publication date in RUL: 24.10.2023

Secondary language

• Language: English
• Title: Electrochemical and thermal transformations of dihydropyrazine derivatives and indole derivatives using graphite electrodes and activated carbon

Abstract

In this study I have examined electrochemical transformations of indole and dihydropyrazine derivatives using graphite electrodes, and thermal conversions of dihydropyrazine derivatives in closed ACE tubes employing activated carbon as a catalyst. Regarding electrochemical transformations, I have tried to build an electrochemical setup from simple commercially available components that would be easy to use as an everyday means of electrochemical synthesis. By using graphite electrodes during the syntheses, I tried to compare their efficiency with more expensive platinum electrodes. In thermal conversions I have tried to test if it is possible to generalize the reaction of aromatization of 5,6-diphenyl-2,3-dihydropyrazine to 2,3-diphenylpyrazine so it would be applicable to other derivatives of dihydropyrazines, which I have synthesised. Reactions were followed with TLC and final products were characterised with spectroscopic methods – 1H NMR and HRMS. I have found that graphite electrodes were suitable for transformations of dihydropyrazine derivatives but with indoles, products were observed only in trace amounts. Regarding thermal aromatization reactions, I have found that such type of reaction can be generalized to various dihydropyrazine derivatives.

• Keywords: electrochemical transformations, dehydrogenation, indoles, dihydropyrazine derivatives, activated carbon