20.500.12556/RUL-186954 Sinteza sterično oviranih 1,2,3-triazolov Synthesis of sterically hindered 1,2,3-triazoles Pripravili smo sterično ovirane 1,4-disubstituirane 1,2,3-triazole iz aril azidov in aril alkinov s CuAAC reakcijo. Raziskovali smo, kako elektronske lastnosti in sterična oviranost substratov vplivajo na potek sinteze. Azide smo uspešno pripravili iz ustreznih anilinov, alkine pa smo poskušali pripraviti s Corey–Fuchsovo reakcijo, spajanjem po Sonogashiri in Seyferth–Gilbertovo homologacijo aldehidov z modifikacijo po Bestmann–Ohiri. Sinteza alkinov je bila zaradi sterične oviranosti in elektronskih lastnosti substratov nekoliko zahtevnejša, vendar smo kljub temu uspešno sintetizirali tri produkte, ki smo jih uporabili za sintezo treh 1,4-disubstituiranih 1,2,3-triazolov z različnimi steričnimi in elektronskimi lastnostmi. Sterically hindered 1,4-disubstituted 1,2,3-triazoles were prepared from aryl azides and aryl alkynes using the CuAAC reaction. The effects of electronic properties and steric hindrance of substrates on the outcome of the synthesis were investigated. Azides were successfully prepared from anilines, while the alkyne syntheses were attempted using the Corey–Fuchs reaction, Sonogashira coupling and Bestmann–Ohira modification of the Seyferth–Gilbert homologation of aldehydes. Alkyne synthesis was relatively challenging due to the unfavorable electronic properties and steric hindrance of the substrates. Nevertheless, three sterically hindered alkynes were successfully prepared and subsequently used to synthesize three 1,4-disubstituted 1,2,3-triazoles with varying steric and electronic properties. 1 2 3-triazoli sterična oviranost CuAAC azid alkin 1 2 3-triazoles steric hindrance CuAAC azide alkyne true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2026-09-08 07:15:06 2026-09-08 07:15:13 2026-09-09 04:22:02 0000-00-00 00:00:00 2026 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 1970-01-01 26199 Pungercar_Vid_-_Sinteza_stericno_oviranih_1,2,3-triazolov.pdf Pungercar_Vid_-_Sinteza_stericno_oviranih_1,2,3-triazolov.pdf 1 20C903966392076F1A310471C1D563F8 217685899d8ea3972792877c3dbd7ef8342d5b774e93f10a1d20af8a67a6f4c7 43b7b7c6-ab44-11f1-8bc5-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=246359 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0