Katalitska fotoredoks C-H arilacija 1-ciano-4-okso-4H-kinolizin-3-diazonijevega tetrafluoroborata z aromatskimi aminokislinskimi derivati

Avsec, Urban (author), Svete, Jurij (mentor)

V diplomskem delu sem izvedel fotoredoks katalizirane C-H arilacije 1-ciano-4-okso-4H-kinolizin-3-diazonijevega tetrafluoroborata (1) z N-Boc-L-fenilalanin metil estrom (2), N-Boc-L-tirozin metil estrom (3), N-Boc-L-histidin metil estrom (4), N-Boc-L-triptofan metil estrom (5) ter z dinatrijevo soljo eozina Y, kot fotokatalizatorjem. Reakcije so potekale pri sobni temperaturi in pri obsevanju z zeleno svetlobo. Pri vseh reakcijah so nastali predvideni regioizomeri produktov arilacije, pri reakciji s histidinom 4, pa sta nastala tudi azo adukta 4c,d. Dobljene produkte sem delno ločil z bliskovito kolonsko kromatografijo in jih okarakteriziral s 1H in 13C spektroskopijo ter HRMS analizo.

• Language: Slovenian
• Keywords: diazonijeva sol, aminokislinski derivati, fotoredoks kataliza, biokonjugacija
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2025
• PID: 20.500.12556/RUL-171440
• COBISS.SI-ID: 247089923
• Publication date in RUL: 26.08.2025

Secondary language

• Language: English
• Title: Catalytic photoredox C-H arylation of 1-cyano-4-oxo-4H-quinolizine-3-diazonium tetrafluoroborate with derivatives of aromatic aminoacids

Abstract

In my thesis, I performed photoredox-catalyzed C-H arylations of 1-cyano-4-oxo-4H- quinolizine-3-diazonium tetrafluoroborate (1) with N-Boc-L-phenylalanine methyl ester (2), N-Boc-L-tyrosine methyl ester (3), N-Boc-L-histidine methyl ester (4) and N-Boc-L- tryptophan methyl ester (5) using the disodium salt of eosin Y as the photocatalyst. The reactions were carried out at room temperature and under green light irradiation. All reactions yielded the expected regioisomers of the arylation products, while the reaction with histidine 4 also yielded azo adducts 4c,d. The obtained products were partially separated by flash column chromatography and characterized by 1H and 13C spectroscopy and HRMS analysis.

• Keywords: diazonium salt, amino acid derivatives, photoredox catalysis, bioconjugation