Sinteza izotiocianatov na osnovi oksindola in njihova uporaba v organokataliziranih pretvorbah

Šegina, Jan (author), Grošelj, Uroš (mentor)

Oksindoli in njihovi spirociklični derivati zaradi svojih bioloških aktivnosti predstavljajo pomembno skupino molekul za tvorbo potencialnih farmacevtskih učinkovin. Te morajo običajno imeti točno določeno stereokemijo, kar dosežemo z uporabo različnih (organo)katalizatorjev. V diplomskem delu v uvodu najprej na kratko opišem zgodovino organokatalize ter prikažem delovanje različnih tipov organokatalizatorjev. Nato predstavim oksindol ter njegove derivate, njihovo uporabo in mehanizme, po katerih se jih da sintetizirati. Opišem tudi postopek, po katerem pridemo iz isatina do 3-izotiocianatooksindola. V četrtem poglavju naredim pregled znanih organokataliziranih reakcij izotiocianatov na osnovi oksindola z različnimi reaktanti, opišem optimalne reakcijske pogoje, katalizatorje, izkoristke in stereoselektivnosti pretvorb. V zaključku naredim kratek povzetek organokataliziranih reakcij in uporabljenih katalizatorjev.

• Language: Slovenian
• Keywords: organokataliza, izotiocianati, oksindol, spirociklični oksindoli, asimetrična sinteza.
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2020
• PID: 20.500.12556/RUL-117333
• COBISS.SI-ID: 22022659
• Publication date in RUL: 07.07.2020

ŠEGINA, Jan, 2020, Sinteza izotiocianatov na osnovi oksindola in njihova uporaba v organokataliziranih pretvorbah [online]. Bachelor’s thesis. [Accessed 30 June 2025]. Retrieved from: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=eng&id=117333

Secondary language

• Language: English
• Title: Synthesis of oxindole-based isothiocyanates and their application in organocatalyzed transformations

Abstract

Due to their varied and complex biological activities, oxindole and its spirocyclic derivatives represent an important group of molecules for the synthesis of potential pharmaceutically active compounds. Chiral active compounds require specific stereochemistry, which is achieved through the use of various (organo)catalysts. In the introduction of the diploma thesis, the history of organocatalysis and the mode of action of different organocatalysts is described, followed by the description of oxindole and its derivatives, their application, and the different mechanisms/routes of their synthesis. A typical procedure for the preparation of 3-isothiocyantooxindole from isatin is described. In the fourth chapter, a survey of known organocatalyzed transformations of isothiocyanates based on oxindole is presented. Optimal reaction conditions, catalysts, yields, and stereoselectivities are included. Closing remarks include a short summary of organocatalyzed transformations and applied catalysts.

• Keywords: organocatalysis, isothiocyanates, oxindole, spirocyclic oxindoles, asymmetric synthesis.